306 results on '"Thiomorpholine"'
Search Results
2. Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry.
- Author
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Palme, Paul R., Goddard, Richard, Imming, Peter, and Seidel, Rüdiger W.
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CHEMICAL precursors , *PHARMACEUTICAL chemistry , *MOLECULAR structure , *MORPHOLINE , *MOLECULAR crystals , *X-ray crystallography , *NUCLEOPHILIC substitution reactions - Abstract
4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately CS-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking. [ABSTRACT FROM AUTHOR]
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- 2024
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3. Structural Characterization of 4-(4-Nitrophenyl)thiomorpholine, a Precursor in Medicinal Chemistry
- Author
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Paul R. Palme, Richard Goddard, Peter Imming, and Rüdiger W. Seidel
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thiomorpholine ,nucleophilic aromatic substitution ,crystal structure ,Hirshfeld surface analysis ,DFT calculation ,hydrogen bonding ,Inorganic chemistry ,QD146-197 - Abstract
4-(4-nitrophenyl)thiomorpholine, the title compound, has been used as a precursor for the corresponding 4-thiomorpholinoaniline, which is a useful building block in medicinal chemistry. The crystal and molecular structures of the title compound, however, have not been described thus far. We synthesized the title compound by means of a nucleophilic aromatic substitution reaction of 4-fluoronitrobenzene and thiomorpholine and structurally characterized it by X-ray crystallography, DFT calculations, and Hirshfeld surface analysis. In the crystal, the molecule exhibits an approximately CS-symmetric structure, with the nitrogen-bound 4-nitrophenyl group in a quasi axial position on the six-membered thiomorpholine ring in a low-energy chair conformation. The solid-state structure of the title compound is markedly different from that of its morpholine analogue. This can be ascribed to the formation of centrosymmetric dimers through intermolecular C–H···O weak hydrogen bonds involving the methylene groups adjacent to the sulfur atom and face-to-face aromatic stacking.
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- 2024
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4. Microwave-supported one-pot reaction for the synthesis of 5-alkyl/arylidene-2-(morpholin/thiomorpholin-4-yl)-1,3-thiazol-4(5H)-one derivatives over MgO solid base
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Nguyen Thi Son, Nguyen Van Duc, Thuy Linh Nguyen Nhat, Nam Anh Pham, Luu Van Boi, and Do Huy Hoang
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morpholine ,thiomorpholine ,thiazolidin-4-one ,microwave ,green chemistry ,solid base mgo ,Chemistry ,QD1-999 - Abstract
In this study, we synthesized 5-alkyl/arylidene-2-(morpholin/thiomorpholin-4-yl)-1,3-thiazol-4(5H)-one through a one-pot reaction using all starting materials in a microwave oven. The presence of the solid base MgO catalyzed the reaction in the eco-friendly solvent of ethanol as a green chemistry approach owing to the noticeable advantages of short reaction times to save energy and less toxic starting materials for environmental friendliness. This indicates that the one-pot reaction makes the process simpler, in which the reaction time (1 h) is shorter than that of conventional methods (10 h). The yield of the reactions reached 55–76% for 18 final products consisting of 17 derivatives of morpholine or thiomorpholine with various aldehydes and one extended moiety of the primary amine, of which 13/18 final compounds were new. The purification procedure was performed without using polluting solvents. The structures were confirmed using IR, 1H-NMR, 13C-NMR, and MS analyses.
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- 2024
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5. (E)-3-Heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide as Solvatochromic and Fluorogenic Dye for Spectroscopy Applications.
- Author
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Vasilev, Aleksey A., Kandinska, Meglena I., Kostadinov, Anton, Dietz, Laura, and Baluschev, Stanislav
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ORGANELLES , *IODIDES , *DYES & dyeing , *SPECTROMETRY , *BENZOTHIAZOLE , *CELL anatomy - Abstract
The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye. [ABSTRACT FROM AUTHOR]
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- 2023
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6. (E)-3-Heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide as Solvatochromic and Fluorogenic Dye for Spectroscopy Applications
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Aleksey A. Vasilev, Meglena I. Kandinska, Anton Kostadinov, Laura Dietz, and Stanislav Baluschev
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fluorogenic probes ,cellular components ,DNA ,RNA ,styryl dyes ,thiomorpholine ,Inorganic chemistry ,QD146-197 - Abstract
The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments may help to determine the mechanism of pathogenesis of new pathogens in living cells. The easy and reliable synthetic strategy for the direct preparation of chemically pure styryl dye (E)-3-heptyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide is described. The photophysical properties in different solvents and in water medium neat and in the presence of the dsDNA and RNA of the dye is demonstrated and compared with that of the known structure analogue. The cellular uptake and the ability to bind cell organelles is determined. The introduction of a heptyl substituent attached to the quaternary nitrogen atom of the benzothiazole ring leads to an improvement in the photophysical properties of the dye.
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- 2023
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7. Styryl Hemicyanine Dye (E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide for Nucleic Acids and Cell Nucleoli Visualization.
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Vasilev, Aleksey A., Miteva, Marina, Ishkitiev, Nikolay, Dragneva, Maria, Topalova, Lora, and Kandinska, Meglena I.
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NUCLEOLUS , *NUCLEIC acids , *IODIDES , *STEM cells , *ARYL iodides , *ETHYL acetate , *VISUALIZATION - Abstract
(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli. [ABSTRACT FROM AUTHOR]
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- 2022
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8. Styryl Hemicyanine Dye (E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium Iodide for Nucleic Acids and Cell Nucleoli Visualization
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Aleksey A. Vasilev, Marina Miteva, Nikolay Ishkitiev, Maria Dragneva, Lora Topalova, and Meglena I. Kandinska
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monomethyne cyanine dyes ,thiomorpholine ,DNA ,stem cells ,apical papilla ,Inorganic chemistry ,QD146-197 - Abstract
(E)-3-Methyl-2-(4-thiomorpholinostyryl)benzo[d]thiazol-3-ium iodide 1 was prepared by a convenient and reliable reaction procedure. The slight molar excess of the starting benzaldehyde and the mixture of ethanol: ethyl acetate in the ratio 3:1 as a solvent afforded a pure reaction product. The photophysical properties of the dye in a TE buffer in the absence and presence of double-stranded DNA (dsDNA) were elucidated. The low intrinsic fluorescence of 1 in TE buffer is followed by an increase in the fluorescence after dsDNA binding. The dye is nontoxic for stem cells from apical papilla and the most concentrated fluorescence is detected in the cell nucleoli.
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- 2022
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9. Amphipol-Mediated Immobilization of Membrane Proteins and Its Applications
- Author
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Popot, Jean-Luc, Aizawa, Masuo, Series Editor, Austin, Robert H., Series Editor, Gerstman, Bernard S., Editor-in-Chief, Barber, James, Series Editor, Berg, Howard C., Series Editor, Callender, Robert, Series Editor, Feher, George, Series Editor, Frauenfelder, Hans, Series Editor, Giaever, Ivar, Series Editor, Joliot, Pierre, Series Editor, Keszthelyi, Lajos, Series Editor, King, Paul W., Series Editor, Lazzi, Gianluca, Series Editor, Lewis, Aaron, Series Editor, Lindsay, Stuart M., Series Editor, Liu, Xiang Yang, Series Editor, Mauzerall, David, Series Editor, Mielczarek, Eugenie V., Series Editor, Niemz, Markolf, Series Editor, Parsegian, V. Adrian, Series Editor, Powers, Linda S., Series Editor, Prohofsky, Earl W., Series Editor, Rostovtseva, Tatiana K., Series Editor, Rubin, Andrew, Series Editor, Seibert, Michael, Series Editor, Tao, Nongjian, Series Editor, Thomas, David, Series Editor, and Popot, Jean-Luc
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- 2018
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10. One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity.
- Author
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Sreerama, Rakesh, T., Narasimha Swamy, M., Ravinder, N., Vasudeva Reddy, and Narsimha, Sirassu
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SULFONYL azides , *MORPHOLINE , *CHEMICAL synthesis , *SULFONIC acids , *TRIAZOLE derivatives , *MASS spectrometry , *FREE radicals - Abstract
A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs. [ABSTRACT FROM AUTHOR]
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- 2021
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11. Synthesis of Oxazine, Thiazine, and Quinoxaline Derivatives Containing a Benzyl Fragment from 3-Aryl-2-Bromopropanoic Acids and Their Esters.
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Pokhodylo, N. T., Martyak, R. L., Rogovyk, M. P., Matiychuk, V. S., and Obushak, M. D.
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QUINOXALINES , *ESTERS , *OXAZINES , *ACIDS , *CYSTEINE , *CHLORIDES - Abstract
3-Aryl-2-bromopropanoic acid esters reacted with o-phenylenediamine, 2-sulfanylaniline, and L-cysteine to give quinoxaline, 1,4-thiazine, and thiomorpholine derivatives, respectively, containing an aryl-methyl substituent. Analogous 1,4-benzoxazine derivatives were synthesized by reactions of 3-aryl-2-bromo-propanoyl chlorides with 2-aminophenol or 2-methoxyaniline. [ABSTRACT FROM AUTHOR]
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- 2021
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12. Reaction of 4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with Morpholine and Thiomorpholine.
- Author
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Fedoseev, S. V. and Ershov, O. E.
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ETHYL acetate , *MORPHOLINE , *ISONICOTINIC acid - Abstract
4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones reacted with morpholine and thiomorpholine in ethyl acetate to give in a few minutes 3-(morpholin-4-yl)- and 3-(thiomorpholin-4-yl)-substituted 4-halofuro-[3,4-c]pyridin-1(3H)-ones. [ABSTRACT FROM AUTHOR]
- Published
- 2021
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13. Polymer-Supported Syntheses of Heterocycles Bearing Oxazine and Thiazine Scaffolds.
- Author
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Králová, Petra, Ručilová, Veronika, and Soural, Miroslav
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- 2018
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14. Synthesis of Oxazine, Thiazine, and Quinoxaline Derivatives Containing a Benzyl Fragment from 3-Aryl-2-Bromopropanoic Acids and Their Esters
- Author
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R. L. Martyak, M. P. Rogovyk, Mykola D. Obushak, Nazariy T. Pokhodylo, and Vasyl S. Matiychuk
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chemistry.chemical_compound ,Thiomorpholine ,Quinoxaline ,chemistry ,Fragment (computer graphics) ,Thiazine ,Aryl ,Organic Chemistry ,Substituent ,Medicinal chemistry - Abstract
3-Aryl-2-bromopropanoic acid esters reacted with o-phenylenediamine, 2-sulfanylaniline, and L-cysteine to give quinoxaline, 1,4-thiazine, and thiomorpholine derivatives, respectively, containing an arylmethyl substituent. Analogous 1,4-benzoxazine derivatives were synthesized by reactions of 3-aryl-2-bromopropanoyl chlorides with 2-aminophenol or 2-methoxyaniline.
- Published
- 2021
15. Lead Sulphide Nanoparticles as Photocatalyst for the Degradation of Methylene Blue: Effects of pH, Time, Adsorption Kinetics and Recyclability Studies
- Author
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Thandi B. Mbuyazi, Abimbola E. Oluwalana, and Peter A. Ajibade
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chemistry.chemical_classification ,Polymers and Plastics ,Scanning electron microscope ,Nanoparticle ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Thiomorpholine ,chemistry ,Materials Chemistry ,Photocatalysis ,0210 nano-technology ,Dithiocarbamate ,Photodegradation ,High-resolution transmission electron microscopy ,Methylene blue ,Nuclear chemistry - Abstract
We report the synthesis and morphological studies of lead sulphide nanoparticles prepared from lead(II) complexes of morpholine dithiocarbamate (PbS1), thiomorpholine dithiocarbamate (PbS2), and N-(2-hydroxyethyl)phenyl dithiocarbamate (PbS3). Powder X-ray diffraction patterns (p-XRD) of the PbS nanoparticles are indexed to face-centered cubic phase of PbS. High-resolution transmission electron microscopy (HRTEM) micrograph revealed quasi-spherical PbS nanoparticles with particle size in the range 13.86–36.06 nm while scanning electron microscopy (SEM) revealed flaky/spherical/rough surface morphology. Photocatalytic degradation of methylene blue dye by the PbS nanoparticles showed degradation efficiency of 72.6 % for PbS1, 75.9 % for PbS2, and 47.4 % for PbS3. The photodegradation efficiency shows a correlation between efficiency and morphological properties. Total organic content removal by PbS2 is 69.5 % while that of PbS1 is 64.2 % and PbS3 is 40.1 %. The as-prepared PbS nanoparticles exhibited remarkable photostability in the recyclability studies.
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- 2021
16. Dassonmycins A and B, Polycyclic Thioalkaloids from a Marine Sponge-Derived Nocardiopsis dassonvillei SCSIO 40065
- Author
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Haibo Zhang, Weimin Zhang, Xinya Zhang, Changsheng Zhang, Li-Ping Zhang, Wenjun Zhang, Qingbo Zhang, Yuchan Chen, and Siqiang Chen
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biology ,010405 organic chemistry ,Nocardiopsis dassonvillei ,Chemistry ,Stereochemistry ,Organic Chemistry ,Ether ,010402 general chemistry ,biology.organism_classification ,Ring (chemistry) ,01 natural sciences ,Biochemistry ,Naphthoquinone ,0104 chemical sciences ,chemistry.chemical_compound ,Sponge ,Piperazine ,Thiomorpholine ,Physical and Theoretical Chemistry - Abstract
Two polycyclic thioalkaloides dassonmycins A (1) and B (2) were isolated from Nocardiopsis dassonvillei SCSIO 40065 associated with marine sponge Petrosia sp. Structures of 1 and 2 were elucidated by comprehensive spectroscopic analysis and confirmed by single-crystal X-ray diffraction experiments, to have a 6/6/6/6-fused tetracyclic ring featuring a naphthoquinone[2,3-e]piperazine[1,2-c]thiomorpholine scaffold. Compound 2 formed a caged core through an additional ether bridge. Both compounds exhibited moderate antibacterial and cytotoxic activities.
- Published
- 2021
17. Elucidating preparation-structure relationships for the morphology evolution during the RAFT dispersion polymerization of N-acryloyl thiomorpholine
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Maren T. Kuchenbrod, Fabian H. Sobotta, Johannes C. Brendel, Stephanie Hoeppener, Christian Grune, and Dagmar Fischer
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chemistry.chemical_classification ,Dispersion polymerization ,Aqueous solution ,Materials science ,Polymers and Plastics ,Organic Chemistry ,Bioengineering ,Raft ,Polymer ,Biochemistry ,chemistry.chemical_compound ,Thiomorpholine ,Monomer ,chemistry ,Polymerization ,Chemical engineering ,Copolymer - Abstract
Polymerization-induced self-assembly (PISA) is an emerging methodology for the in situ preparation of complex polymeric nanostructures in aqueous solution. However, the scope of monomers allowing morphology transitions remains limited, which is related to the low solubility of many monomers in water. Morphology transitions have therefore been restricted to more hydrophilic monomers necessitating rather long hydrophobic blocks to induce aggregation. Even longer ones are required to induce the changes of the morphology deviating from a spherical shape – a fact that limits the accessible hydrophobic domain sizes or morphologies. Here, we demonstrate that N-acryloyl thiomorpholine (NAT) represents a unique monomer which is fully miscible with water, but results in hydrophobic polymers at degrees of polymerization (DP) below 10, while morphology transitions can occur at DPs of 25 and even less. Synthesizing over 70 block copolymers in total we identified key parameters, such as hydrophilic block length, temperature, ratio of co-solvent, and concentration, influencing the self-assembly process. While the high glass transition temperature (Tg) of PNAT may cause frozen and kinetically trapped micellar cores, suitable synthesis conditions enable access to all common morphologies including spheres, worms, and vesicles as well as intermediate phases. Applying this technique, various nanostructures are reproducibly formed in situ in aqueous dispersions rendering the presented PISA system a highly versatile, new route to functional block copolymer nanostructures for various applications.
- Published
- 2021
18. One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity
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N. Vasudeva Reddy, Mettu Ravinder, Rakesh Sreerama, T Narasimha Swamy, and Sirassu Narsimha
- Subjects
Sulfonyl ,chemistry.chemical_classification ,1,2,3-Triazole ,010405 organic chemistry ,Organic Chemistry ,One-pot synthesis ,Biological activity ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,Thiomorpholine ,chemistry ,Organic chemistry ,Antibacterial activity - Abstract
A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.
- Published
- 2020
19. Polymer-Supported Stereoselective Synthesis of Benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides.
- Author
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Králová, Petra, Maloň, Michal, Volná, Tereza, Ručilová, Veronika, and Soural, Miroslav
- Abstract
Herein, we report the stereoselective synthesis of trisubstituted benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides from polymer-supported Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH. After the solid-phase synthesis of N-alkylated-N-sulfonylated intermediates using various 2-nitrobenzenesulfonyl chlorides and bromoketones, the target compounds were obtained via trifluoroacetic acid (TFA)-mediated cleavage from the resin, followed by cyclization of the diazepinone scaffold. Except for the threonine-based intermediates, the inclusion of triethylsilane (TES) in the cleavage cocktail yielded a specific configuration of the newly formed C3 chiral center. The final cyclization resulted in minor or no inversion of the C12a stereocenter configuration. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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20. Synthesis and biological evaluation of novel indole-pyrimidine hybrids bearing morpholine and thiomorpholine moieties.
- Author
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Diao, Peng-Cheng, Li, Qiu, Hu, Meng-Jin, Ma, Yu-Feng, You, Wen-Wei, Hong, Kwon Ho, and Zhao, Pei-Liang
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PYRIMIDINES , *MORPHOLINE , *HELA cells , *TUBULINS , *POLYMERIZATION , *MOIETIES (Chemistry) , *ANTINEOPLASTIC agents - Abstract
Based on our previous screening hit compound 1 , a series of novel indole-pyrimidine hybrids possessing morpholine or thiomorpholine moiety were synthesized via an efficient one-pot multistep synthetic method. The antiproliferative activities of the synthesized compounds were evaluated in vitro against four cancer cell lines including HeLa, MDA-MB-231, MCF-7, and HCT116. The results revealed that most compounds possessed moderate to excellent potency. The IC 50 values of the most promising compound 15 are 0.29, 4.04, and 9.48 μM against MCF-7, HeLa, and HCT116 cell lines, respectively, which are 48.0, 4.9, and 1.8 folds more active than the lead compound 1 . Moreover, fluorescence-activated cell sorting analysis revealed that compound 14 showing the highest activity against HeLa (IC 50 = 2.51 μM) displayed a significant effect on G 2 /M cell-cycle arrest in a concentration-dependent manner in HeLa cell line. In addition, representative nine active hybrids were evaluated for tubulin polymerization inhibitory activities, and compound 15 exhibited the most potent anti-tubulin activity showing 42% inhibition at 10 μM. These preliminary results encourage a further investigation on indole-pyrimidine hybrids for the development of potent anticancer agents that inhibit tubulin polymerization. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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21. Stereoselective Polymer-Supported Synthesis of Morpholine- and Thiomorpholine-3-carboxylic Acid Derivatives.
- Author
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Králová, Petra, Fülöpová, Veronika, Maloň, Michal, Volná, Tereza, Popa, Igor, and Soural, Miroslav
- Abstract
Herein we report the polymer-supported synthesis of 3,4-dihydro-2H-1,4-oxazine-3-carboxylic acid derivatives using immobilized Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH as the starting materials. After the solid-phase-synthesis of N-alkyl-N-sulfonyl/acyl intermediates, the target dihydrooxazines were obtained using trifluoroacetic acid-mediated cleavage from the resin. This approach was also studied for the preparation of dihydrothiazines from immobilized Fmoc-Cys(Trt)-OH. Inclusion of triethylsilane in the cleavage cocktail resulted in the stereoselective formation of the corresponding morpholine/thiomorpholine-3-carboxylic acids. Stereochemical studies revealed the specific configuration of the newly formed stereocenter and also the formation of stable N-acylmorpholine rotamers. [ABSTRACT FROM AUTHOR]
- Published
- 2017
- Full Text
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22. Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study
- Author
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Agnieszka Chylewska, Morgan Donnard, Marko V. Rodić, Predrag Ristić, Goran V. Janjić, Mariusz Makowski, Vladimir A. Blagojević, Mihaela Gulea, Tamara R. Todorović, Nenad Filipovic, Predrag Vulić, Laboratoire d'innovation moléculaire et applications (LIMA), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'Innovation Thérapeutique (LIT), and Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)
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crystal structure ,metals ,molecular structure ,Crystal structure ,010402 general chemistry ,DFT ,01 natural sciences ,Pd(II) ,chemistry.chemical_compound ,C–H/Cl interactions ,Molecule ,General Materials Science ,Pt(II) ,Pd complexes ,Molecular interactions ,M–S bond ,ligands ,010405 organic chemistry ,C–H/S interactions ,General Chemistry ,C–H/M interactions ,Condensed Matter Physics ,Pt complexes ,0104 chemical sciences ,Crystallography ,Thiomorpholine ,chemistry ,[CHIM.OTHE]Chemical Sciences/Other ,Derivative (chemistry) ,molecular interactions - Abstract
Pt(II) and Pd(II) complexes (1 and 2, respectively) with thiomorpholine-4-carbonitrile (TM-CN), an N-substituted thiomorpholine derivative, were synthesized from tetrachlorido precursors in water. Structural analysis has shown that 1 represents the first monomeric metal complex with this ligand type with an axial M–S bond with respect to the TM-CN ring chair conformation, while in 2 a typical equatorial M–S bond position with respect to the ring chair conformation was observed. A detailed DFT investigation revealed that axial conformers are more stable for molecular forms of both metals, while intermolecular interactions in the crystals stabilize the axial conformer for Pt(II) and the equatorial conformer for Pd(II). The magnitude of this stabilization in the case of 2 is large enough to change the most stable axial conformer in the molecular form to the equatorial conformer in the crystal. Further investigation of the strength of individual intermolecular interactions revealed significant differences of some interactions between the two structures. The likely cause of the difference in the crystal structures of experimentally obtained complexes is the fact that 1 and 2 exhibit different dominant interactions: C–H/M and C–H/S are more dominant in 1 and C–H/Cl interactions are more dominant in 2. In addition, DFT calculations have shown that while the axial position of the Pt–S bond with respect to the ring chair conformation results in a significantly shorter C–H/Pt interaction distance than that in the hypothetical equatorial conformer, there is very little difference in C–H/Pd interaction distances in conformers with axial and equatorial positions of Pd–S bond with respect to the ring chair conformation. This is the peer-reviewed version of the article: Predrag Ristić, Vladimir Blagojević, Goran Janjić, Marko Rodić, Predrag Vulić, Morgan Donnard, Mihaela Gulea, Agnieszka Chylewska, Mariusz Makowski, Tamara Todorović, Nenad Filipović, Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study, Cryst. Growth Des. 2020, 20, 5, 3018–3033, DOI: [https://doi.org/10.1021/acs.cgd.9b01661] The published version: [https://cer.ihtm.bg.ac.rs/handle/123456789/4028]
- Published
- 2020
23. Thioether-Based Polymeric Micelles with Fine-Tuned Oxidation Sensitivities for Chemotherapeutic Drug Delivery
- Author
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Masoud Ghasemi, Bin Liu, Enrique D. Gomez, Urara Hasegawa, André J. van der Vlies, Jiayi Xu, Amanda Bell, Brett Rosoff-Verbit, and Carol M. Bator
- Subjects
Polymers and Plastics ,Cell Survival ,Substituent ,Bioengineering ,Sulfides ,Micelle ,Redox ,Article ,Biomaterials ,chemistry.chemical_compound ,Drug Delivery Systems ,Thioether ,Materials Chemistry ,Humans ,Reactivity (chemistry) ,Hydrogen peroxide ,Micelles ,Drug Carriers ,Endothelial Cells ,Hydrogen Peroxide ,Hydrogen-Ion Concentration ,Combinatorial chemistry ,Drug Liberation ,Thiomorpholine ,chemistry ,Doxorubicin ,Drug delivery - Abstract
Oxidation-sensitive drug delivery systems (DDS) have attracted attention due to the potential to improve efficacy and safety of chemotherapeutics. These systems are designed to release the payload in response to oxidative stress conditions, which are associated with many types of cancer. Despite extensive research on the development of oxidation-sensitive DDS, the lack of selectivity towards cancer cells over healthy cells remains a challenge. Here, we report the design and characterization of polymeric micelles containing thioether groups with varying oxidation sensitivities within the micellar core, which become hydrophilic upon thioether oxidation leading to destabilization of the micellar structure. We first used the thioether model compounds, 3-methylthiopropylamide (TPAM), thiomorpholine amide (TMAM), and 4-(methylthio)benzylamide (TPhAM), to investigate the effect of the chemical structures of the thioethers on the oxidation by hydrogen peroxide [Formula: see text]. TPAM shows the fastest oxidation followed by TMAM and TPhAM, showing that the oxidation reaction of thioethers can be modulated by changing the substituent groups bound to the sulfur atom. We next prepared micelles containing these different thioether groups within the core (TP, TM and TPh micelles). The micelles containing the thioether groups with a higher oxidation sensitivity were destabilized by [Formula: see text] at lower concentration. Micelle destabilization was also tested in human liver cancer (HepG2) cells and human umbilical vein endothelial cells (HUVECs). The TP micelles having the highest oxidation sensitivity were destabilized in both HepG2 cells and HUVECs while the TPh micelles, which showed the lowest reactivity towards [Formula: see text] , were stable in those cell lines. The TM micelles possessing a moderate oxidation sensitivity were destabilized in HepG2 cells but were stable in HUVECs. Furthermore, the micelles were loaded with doxorubicin (Dox) to evaluate their potential in drug delivery applications. Among the micelles, the TM micelles loaded with Dox showed the enhanced relative toxicity in HepG2 cells over HUVECs. Therefore, our approach to fine-tune the oxidation sensitivity of the micelles has potential for improving therapeutic efficacy and safety of drugs in cancer treatment.
- Published
- 2021
24. Reaction of 4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with Morpholine and Thiomorpholine
- Author
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Sergey V. Fedoseev and O. E. Ershov
- Subjects
chemistry.chemical_compound ,Thiomorpholine ,chemistry ,010405 organic chemistry ,Morpholine ,Organic Chemistry ,Ethyl acetate ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences - Abstract
4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones reacted with morpholine and thiomorpholine in ethyl acetate to give in a few minutes 3-(morpholin-4-yl)- and 3-(thiomorpholin-4-yl)-substituted 4-halofuro[3,4-c]pyridin-1(3H)-ones.
- Published
- 2021
25. Crystal structure of 2-methylsulfanyl-1-(thiomorpholin-4-yl)ethanone
- Author
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Gihaeng Kang, Jineun Kim, Eunjin Kwon, and Tae Ho Kim
- Subjects
crystal structure ,thiomorpholine ,hydrogen bonding ,Crystallography ,QD901-999 - Abstract
In the title compound, C7H13NOS2, the thiomorpholine ring adopts a chair conformation and the bond-angle sum at the N atom is 360°. The dihedral angle between the amide group and the thiomorpholine ring (all atoms) is 36.48 (12)°. In the crystal, C—H...O and C—H...S hydrogen bonds link adjacent molecules, forming two-dimensional networks extending parellel to the (011) plane.
- Published
- 2015
- Full Text
- View/download PDF
26. Synthesis of new pyrazolo[5,1-c][1,2,4]triazines with antifungal and antibiofilm activities
- Author
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Salah A. Al-Trawneh, Shoroq A. Al-Dawdieh, Ehab A. Salama, Mustafa M. El-Abadelah, Nader S. Abutaleb, Amer H. Tarawneh, and Mohamed N. Seleem
- Subjects
General Chemical Engineering ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Industrial and Manufacturing Engineering ,chemistry.chemical_compound ,Minimum inhibitory concentration ,Morpholine ,Materials Chemistry ,medicine ,Candida albicans ,Triazine ,biology ,General Chemistry ,021001 nanoscience & nanotechnology ,biology.organism_classification ,Combinatorial chemistry ,Corpus albicans ,0104 chemical sciences ,Thiomorpholine ,chemistry ,Growth inhibition ,0210 nano-technology ,Fluconazole ,medicine.drug - Abstract
Fungal infection is a significant global health challenge in part due to the emergence of strains exhibiting resistance to nearly all classes of antifungals. This underscores the urgent need for the development of new antifungal agents that can circumvent this burgeoning problem. For the present research, a new selected set of pyrazolo[5,1-c][1,2,4]triazine derivatives 3a–g was prepared in high yield via the reaction of N1-(5-methylpyrazol-3-yl)hydrazonoyl chloride 1 with morpholine, thiomorpholine, 4-phenylpiperidine and N-(substituted)piperazines. The new compounds were evaluated for their in vitro antifungal and antibacterial activities. The screening revealed compounds with specific activity against pathogenic fungi, including Candida albicans, Candida auris, and Cryptococcus. Compound 3d, which incorporated N-phenylpiperazine moiety, exhibited the highest growth inhibition against C. albicans with a minimum inhibitory concentration of 16 µg/mL. The compounds were superior to fluconazole in inhibiting Candida biofilm mass at sub-inhibitory concentration. Furthermore, the MTS assay confirmed that compounds 1 and 3d exhibited an excellent toxicity profile (not toxic, up to 256 μg/mL, for mammalian cells). Collectively, the presented results demonstrate that the synthesized pyrazolo-triazines warrant further exploration for potential use as antifungal agents.
- Published
- 2019
27. Synthesis, spectroscopic characterization, DFT studies, and preliminary antimicrobial evaluation of new antimony(III) and bismuth(III) complexes derived from 1,3,5-triazine
- Author
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Gerd B. Rocha, Edeltrudes de Oliveira Lima, Evandro Paulo Soares Martins, Felipe T. Martins, and Mário L. A. A. Vasconcellos
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Thermogravimetric analysis ,biology ,Chemical shift ,Organic Chemistry ,Carbon-13 NMR ,biology.organism_classification ,Analytical Chemistry ,Inorganic Chemistry ,Candida tropicalis ,Piperazine ,chemistry.chemical_compound ,Thiomorpholine ,chemistry ,1,3,5-Triazine ,Candida krusei ,Spectroscopy ,Nuclear chemistry - Abstract
Herein, we describe the synthesis and characterizations of 2,4,6-tris(thiomorpholine)-1,3,5-triazine, 2,4,6-tris(piperazine)-1,3,5-triazine and their new Sb(III) and Bi(III) complexes. Characterizations of the ligands and complexes were carried out by elemental analysis, thermogravimetric analysis (TGA), and spectroscopic methods such as infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), and single crystal X-ray. Theoretical vibrational frequencies and 1H and13C NMR chemical shifts of free ligands as well as their Sb(III) and Bi(III) complexes have been calculated using density functional theory (DFT/B3LYP and M06-2X) methods. Our theoretical results matched the corresponding experimental data and helped with the interpretation of the IR and 1H and 13C NMR spectra. The antimicrobial in vitro studies were carried out against bacterial species Staphylococcus aureus and fungal species Candida albicans, Candida tropicalis, and Candida krusei by the microdilution method. The preliminary antimicrobial evaluations indicated that Sb(III) complexes showed moderate activities against all tested strains of bacterial and fungal with minimum inhibitory concentration (MIC) in range of 512–1024 μg mL−1.
- Published
- 2019
28. A novel hydrogel containing thioether group as selective support material for preparation of gold nanoparticles: Synthesis and catalytic applications
- Author
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Pinar Ilgin, Hava Ozay, and Ozgur Ozay
- Subjects
Reducing agent ,Process Chemistry and Technology ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Catalysis ,0104 chemical sciences ,chemistry.chemical_compound ,Thiomorpholine ,Monomer ,Thioether ,chemistry ,Polymerization ,Colloidal gold ,Self-healing hydrogels ,0210 nano-technology ,General Environmental Science ,Nuclear chemistry - Abstract
In this study, firstly N-metacrylamido thiomorpholine containing thioether group was synthesized as monomer. Then, p(AAm-co-MTM) hydrogels were prepared from the redox polymerization of acrylamide and N-metacrylamido thiomorpholine as a selective support material. p(AAm-co-MTM) hydrogel-gold nanoparticles were obtained as a result of the reduction of the selectively absorbed gold(III) ions by the hydrogel network using NaBH4 as reducing agent. All materials were characterized using techniques such as SEM, EDX, TEM and XRD analysis. It was determined that p(AAm-co-MTM)-Au composite material has high catalytic activity for the reduction of 4-nitrophenol. The activation parameters of the reduction reaction of 4-nitrophenol using NaBH4 in the presence of p(AAm-co-MTM)-Au catalyst were calculated as Ea = 38.80 kJ/mol, ΔH# = 36.16 kJ/mol and ΔS#= −161.37 J/mol K.
- Published
- 2019
29. Copper Catalyzed Synthesis of Thiomorpholine Derivatives: A New Entry of Multicomponent Reaction Between Terminal Alkynes, Isothiocyanates, and Aziridines
- Author
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Alireza Samzadeh‐Kermani
- Subjects
chemistry.chemical_compound ,Thiomorpholine ,Terminal (electronics) ,chemistry ,010405 organic chemistry ,Organic Chemistry ,Copper catalyzed ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences - Published
- 2018
30. Morpholine- and Thiomorpholine-Based Amidodithiophosphonato Nickel Complexes: Synthesis, Characterization, P-N Cleavage, Antibacterial Activity and Silica Nano-Dispersion
- Author
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Enrico Podda, M. Carla Aragoni, Massimiliano Arca, Giulia Atzeni, Simon J. Coles, Guido Ennas, Francesco Isaia, Vito Lippolis, Germano Orru, Alessandra Scano, James B. Orton, and Anna Pintus
- Subjects
Materials science ,Biomedical Engineering ,chemistry.chemical_element ,Bioengineering ,010402 general chemistry ,01 natural sciences ,Metal ,03 medical and health sciences ,Hydrolysis ,chemistry.chemical_compound ,Morpholine ,General Materials Science ,Reactivity (chemistry) ,0303 health sciences ,030306 microbiology ,Sorption ,General Chemistry ,Condensed Matter Physics ,0104 chemical sciences ,Nickel ,Thiomorpholine ,chemistry ,visual_art ,visual_art.visual_art_medium ,Antibacterial activity ,Nuclear chemistry - Abstract
The reactivity of thiomorpholinium P-(4-methoxyphenyl)-N-thiomorpholin-amidodithiophosphonate (S-MorH+2)(S-Mor-adtp−) and morpholinium P-(4-methoxyphenyl)-N-morpholin-amidodithiophosphonate (O-MorH+2)(O-Mor-adtp−) towards nickel (II) dichloride hexahydrated is presented and the hydrolysis of the relevant metal complexes investigated. The hydrolytic products (S-MorH+2)2 [Ni(dtp)2]2− and (O-MorH+2)2[Ni(dtp)2]2− were characterized by means of FT-IR, 1H, and 31P NMR and XRD and the experimented P–N cleavage investigated and elucidated by means of DFT calculations. The antimicrobial activity of the neutral nickel complex [Ni(S-Mor-adtp)2] was tested against a set of Gram-positive and Gram-negative bacteria alongside with its nanodispersion in a silica matrix. The complex [Ni(S-Mor-adtp)2] did not show antibacterial activity, whilst the nano-dispersed sample [Ni(S-Mor-adtp)2]_SiO2 demonstrated inhibition to growth of Staphylococcus aureus. The nanocomposites were fully characterized by means of XRPD, TGA, SEM and dinitrogen sorption techniques.
- Published
- 2021
31. Tedaniophorbasins A and B—Novel Fluorescent Pteridine Alkaloids Incorporating a Thiomorpholine from the Sponge Tedaniophorbas ceratosis
- Author
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Asadhawut Hiranrat, Vicky M Avery, Wilawan Mahabusarakam, Anthony R. Carroll, Darren C. Holland, and J.N.A. Hooper
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Magnetic Resonance Spectroscopy ,Stereochemistry ,Plasmodium falciparum ,Trypanosoma brucei brucei ,malaria ,Pharmaceutical Science ,Tedaniophorbas ceratosis ,Antineoplastic Agents ,Trypanosoma brucei ,010402 general chemistry ,01 natural sciences ,Article ,tedaniophorbasin A ,sponge ,pteridine alkaloids ,chemistry.chemical_compound ,Alkaloids ,Cell Line, Tumor ,Drug Discovery ,parasitic diseases ,medicine ,Animals ,Humans ,Pharmacology, Toxicology and Pharmaceutics (miscellaneous) ,lcsh:QH301-705.5 ,biology ,010405 organic chemistry ,Alkaloid ,Pteridines ,Carbon-13 NMR ,biology.organism_classification ,Fluorescence ,0104 chemical sciences ,Porifera ,Thiomorpholine ,chemistry ,lcsh:Biology (General) ,fluorescence ,Two-dimensional nuclear magnetic resonance spectroscopy ,Pteridine ,medicine.drug - Abstract
Two new fluorescent pteridine alkaloids, tedaniophorbasins A (1) and B (2), together with the known alkaloid N-methyltryptamine, were isolated, through application of mass directed purification, from the sponge Tedaniophorbas ceratosis collected from northern New South Wales, Australia. The structures of tedaniophorbasins A and B were deduced from the analysis of 1D/2D NMR and MS data and through application of 13C NMR DFT calculations. Tedaniophorbasin A possesses a novel 2-imino-1,3-dimethyl-2,3,7,8-tetrahydro-1H-[1,4]thiazino[3,2-g]pteridin-4(6H)-one skeleton, while tedaniophorbasin B is its 2-oxo derivative. The compounds show significant Stokes shifts (~14,000 cm−1) between excitation and emission wavelengths in their fluorescence spectra. The new compounds were tested for bioactivity against chloroquine-sensitive and chloroquine-resistant strains of the malaria parasite Plasmodium falciparum, breast and pancreatic cancer cell lines, and the protozoan parasite Trypanosoma brucei brucei but were inactive against all targets at 40 µM.
- Published
- 2021
32. Synthesis and Characterization of S,S-, S,S,S-, and Thiomorpholinyl-Substituted Nitrodiene Compounds and a Structural Study.
- Author
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Gokmen, Zeliha and Deniz, Nahide Gulsah
- Subjects
- *
SULFUR compounds synthesis , *SUBSTITUTION reactions , *THIOL synthesis , *SODIUM hydroxide , *RING formation (Chemistry) - Abstract
S,S- and S,S,S-substituted nitrodienes3a,3b, and4awere synthesized by reactions of 1,1,2,4,4-pentachloro-3-nitro-1,3-butadiene with some thiols 4-chlorobenzylmercaptan and 2-chlorobenzylmercaptan in ethanol in the presence of sodium hydroxide. Thiomorpholine ring substituted nitrodienes6cand6dand were obtained from the reactions of the mono(thio)substituted nitrodienes with thiomorpholine in dichloromethane. The single crystal X-ray structure of 4-(1-thiomorpholinyl)-4-(butylsulfanyl)-1,1,2-trichloro-3-nitro-1,3-butadiene (6c) is reported. In this present paper, the structures of new compounds were characterized by using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and Fourier transform infrared (FTIR) spectroscopy spectroscopic data. [ABSTRACT FROM AUTHOR]
- Published
- 2015
- Full Text
- View/download PDF
33. Synthesis of 5-(het)aryl- and 4,5-di(het)aryl-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via S and cross-coupling reactions.
- Author
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Cheprakova, E., Verbitskiy, E., Ezhikova, M., Kodess, M., Pervova, M., Slepukhin, P., Toporova, M., Kravchenko, M., Medvinskiy, I., Rusinov, G., and Charushin, V.
- Subjects
- *
MYCOBACTERIUM tuberculosis , *PYRIMIDINE derivatives , *COUPLING reactions (Chemistry) , *NUCLEOPHILIC aromatic photosubstitution , *HYDROGEN bonding - Abstract
It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (S), S and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)aryl-2-(thio)morpholinopyrimidine and 4,5-di(het)aryl-2-(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis HRv. [ABSTRACT FROM AUTHOR]
- Published
- 2014
- Full Text
- View/download PDF
34. Complexation, thermal and catalytic studies of N-substituted piperazine, morpholine and thiomorpholine with some metal ions.
- Author
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Kacan, Mesut, Turkyilmaz, Murat, Karabulut, Ferhat, Altun, Ozlen, and Baran, Yakup
- Subjects
- *
COMPLEXATION reactions , *CATALYTIC activity , *PIPERAZINE , *MORPHOLINE , *METAL ions , *METAL complexes - Abstract
Highlights: [•] Nine new metal complexes were prepared. [•] Catalytic activity of the complexes were studied. [•] Thermal stabilities of the complexes were determined. [•] Cataltytic epoxidation of cis-diphenylethylene was studied. [Copyright &y& Elsevier]
- Published
- 2014
- Full Text
- View/download PDF
35. Metabolite-Based Modification of Poly(l-lysine) for Improved Gene Delivery
- Author
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Raffaele Colombo, Morgan Urello, Alexander Ma, Lucia Xiang, Herren Wu, R. James Christie, Changshou Gao, Norman C. Peterson, Jonathan Boyd, and Augustine Joseph
- Subjects
Polymers and Plastics ,Biocompatibility ,Metabolite ,Bioengineering ,02 engineering and technology ,Gene delivery ,010402 general chemistry ,Transfection ,01 natural sciences ,Polyethylene Glycols ,Biomaterials ,chemistry.chemical_compound ,In vivo ,Morpholine ,Materials Chemistry ,Polylysine ,Gene Transfer Techniques ,DNA ,Genetic Therapy ,021001 nanoscience & nanotechnology ,0104 chemical sciences ,Thiomorpholine ,chemistry ,Biophysics ,0210 nano-technology - Abstract
Synthetic gene delivery systems employ multiple functions to enable safe and effective transport of DNA to target cells. Here, we describe metabolite-based poly(l-lysine) (PLL) modifiers that improve transfection by imparting both pH buffering and nanoparticle stabilization functions within a single molecular unit. PLL modifiers were based on morpholine (M), morpholine and niacin (MN), or thiomorpholine (TM). PLL modification with (MN) or (TM) imparted buffering function over the pH range of 5-7 both in solution and live cells and enhanced the stability of PLL DNA nanoparticles, which exhibited higher resistance to polyanion exchange and prolonged blood circulation. These properties translated into increased transfection efficiency in vitro coupled with reduced toxicity compared to unmodified PLL and PLL(M). Furthermore, PEG-PLL(MN) DNA nanoparticles transfected muscle tissue in vivo for >45 days following intramuscular injection. These polymer modifiers demonstrate the successful design of multifunctional units that improve transfection of synthetic gene delivery systems while maintaining biocompatibility.
- Published
- 2020
36. 1D and 2D Silver-Based Coordination Polymers with Thiomorpholine-4-carbonitrile and Aromatic Polyoxoacids as Coligands: Structure, Photocatalysis, Photoluminescence, and TD-DFT Study
- Author
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Predrag Ristić, Predrag Vulić, Olivera R. Klisurić, Miguel Monge, Vladimir A. Blagojević, Ivana Marjanović, Tamara R. Todorović, Morgan Donnard, Nenad Filipovic, María Rodríguez-Castillo, Berta Barta Holló, José M. López-de-Luzuriaga, Mihaela Gulea, Laboratoire d'Innovation Thérapeutique (LIT), Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC), Laboratoire d'innovation moléculaire et applications (LIMA), and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Materials science ,Photoluminescence ,010402 general chemistry ,01 natural sciences ,Metal ,chemistry.chemical_compound ,General Materials Science ,Singlet state ,Photocatalysis ,Intermolecular interactions ,010405 organic chemistry ,Ligand ,ligands ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Intermolecular force ,Silver complexes ,General Chemistry ,Condensed Matter Physics ,0104 chemical sciences ,Coordination polymers ,Crystallography ,coordination polymers ,Thiomorpholine ,chemistry ,visual_art ,visual_art.visual_art_medium ,photoluminescence ,Luminescence ,TD-DFT ,photocatalysis - Abstract
Four silver-based coordination polymers, {[Ag(L)2](BF4)}∞ (1), {[Ag(H2BTC)(L)]·(H3BTC)}∞ (2), {[Ag2(H2BTEC)(L)2]·3.33H2O}∞ (3), and [Ag(H25SSA)(L)]∞ (4), were synthesized using thiomorpholine-4-carbonitrile (L) as the primary ligand and three aromatic polyoxoacids as coligands: trimesic (H3BTC), pyromellitic (H4BTEC), and 5-sulfosalicylic acid (H35SSA). Compounds 1 and 3 are two-dimensional, while 2 and 4 are one-dimensional. L acts as a bis-monodentate ligand, while the Ag(I) ion is three-coordinated in 2 and four-coordinated in all of the other compounds. The tetrahedral coordination of Ag(I) in 3 leads to an almost complete absence of intermolecular interactions with the metal center. All compounds show reasonable photocatalytic activity for photocatalytic degradation of mordant blue 9 dye, with reaction rates in the 0.036–0.056 min–1 range. Changes in the reaction rates can be correlated with the type and coordination of the coligand. Complex 3 exhibits photoluminescence at 77 K, while 4 exhibits photoluminescence at both room temperature and 77 K. Luminescence lifetimes indicate electronic transitions of singlet parentage, where transitions are allowed. A TD-DFT study determined the contributions of individual singlet–singlet electronic excitations to the fluorescence, indicating that metal– intraligand transitions are responsible for luminescence in both complexes. This is the peer-reviewed version of the article: Ristić, P.; Todorović, T. R.; Blagojević, V.; Klisurić, O. R.; Marjanović, I.; Holló, B. B.; Vulić, P.; Gulea, M.; Donnard, M.; Monge, M.; Rodríguez-Castillo, M.; López-de-Luzuriaga, J. M.; Filipović, N. R. 1D and 2D Silver-Based Coordination Polymers with Thiomorpholine-4-Carbonitrile and Aromatic Polyoxoacids as Coligands: Structure, Photocatalysis, Photoluminescence, and TD-DFT Study. Crystal Growth & Design 2020, 20 (7), 4461–4478. [https://doi.org/10.1021/acs.cgd.0c00287] Supplementary material: [https://cherry.chem.bg.ac.rs/handle/123456789/4206]
- Published
- 2020
37. Polymer-Supported Syntheses of Heterocycles Bearing Oxazine and Thiazine Scaffolds
- Author
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Veronika Ručilová, Miroslav Soural, and Petra Králová
- Subjects
Polymers ,Morpholines ,Thiazines ,010402 general chemistry ,01 natural sciences ,Small Molecule Libraries ,chemistry.chemical_compound ,Solid-phase synthesis ,Thiazine ,Morpholine ,Oxazines ,Solid-Phase Synthesis Techniques ,Cycloaddition Reaction ,Molecular Structure ,010405 organic chemistry ,Stereoisomerism ,General Chemistry ,General Medicine ,Combinatorial chemistry ,0104 chemical sciences ,Thiomorpholine ,chemistry ,Pyrazoles ,Literature survey ,Oxidation-Reduction ,Polymer supported - Abstract
In this review, we summarize synthetic approaches to preparing single or fused oxazine and thiazine derivatives using solid-phase synthesis (SPS). The literature survey revealed that diverse compounds bearing variously functionalized 1,2-oxazine, 1,3-oxazine, or 1,4-oxazine scaffolds and the corresponding thiazines are accessible by SPS. The latest contributions involving the stereoselective polymer-supported syntheses of morpholines indicate that the field is continuing to expand.
- Published
- 2018
38. Amine over-alkylation side products in the synthesis of BMS-955176
- Author
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Alice Yang, Matthew W. Haley, Susanne Kiau, Sloan Ayers, Zhongmin Xu, and Regina Black
- Subjects
0301 basic medicine ,Primary (chemistry) ,Chemistry ,Maturation inhibitor ,030106 microbiology ,Organic Chemistry ,Alkylation ,Biochemistry ,Combinatorial chemistry ,03 medical and health sciences ,chemistry.chemical_compound ,Thiomorpholine ,Drug Discovery ,Side chain ,Molecule ,Amine gas treating ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
Over-alkylation side products are common in the alkylation of amines by substitution. In the synthesis of the novel HIV Maturation inhibitor BMS-955176, two over-alkylation byproducts were routinely observed at the penultimate synthetic step, in which a thiomorpholine dioxide side chain was added to the core molecule by alkylation of a primary amine. These two byproducts had drastically different HPLC relative retention times, despite both containing only one additional side chain. Adding complexity to the challenge of solving their structures was the proclivity of the two byproducts to interconvert. Positive- and negative-ion HRMS, as well as isolation and 1D and 2D NMR were utilized to determine their structures. These byproducts were additionally problematic in that they led to daughter impurities at the API step.
- Published
- 2018
39. Development of a Safe and High-Throughput Continuous Manufacturing Approach to 4-(2-Hydroxyethyl)thiomorpholine 1,1-Dioxide
- Author
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Neil A. Strotman, Kyle W. Powers, Yichen Tan, Simon Leung, and Maxime Soumeillant
- Subjects
Exothermic reaction ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences ,Solvent ,chemistry.chemical_compound ,Thiomorpholine ,Ethanolamine ,Volume (thermodynamics) ,Moiety ,Steady state (chemistry) ,Physical and Theoretical Chemistry ,Conjugate - Abstract
Continuous processing enabled the highly energetic double conjugate addition of ethanolamine to divinylsulfone to prepare 2 kg of 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide, as an intermediate in the synthesis of HIV Maturation Inhibitor BMS-955176. In situ IR was employed to monitor the steady state of the transformation for increased robustness via appearance of the thiomorpholine dioxide moiety and disappearance of the divinylsulfone. Surprisingly, a series of oligomers formed as intermediates, which converted to product with extended aging or heating, consistent with computational predictions. By running this process in flow, the highly exothermic reaction could be safely executed in an equal volume of water as the only solvent, despite an adiabatic temperature rise of 142 °C, leading to a streamlined and efficient process.
- Published
- 2018
40. Regulating glutathione-responsiveness of naphthalimide-based fluorescent probes by an oxidation strategy
- Author
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Fengying Ye, Guotao Liu, Sheng Hua Liu, Weijie Chen, Zhiqiang Xu, Yingle Pan, Lintao Zeng, Jun Yin, and Xiaoqiang Chen
- Subjects
chemistry.chemical_classification ,Organic Chemistry ,02 engineering and technology ,Glutathione ,010402 general chemistry ,021001 nanoscience & nanotechnology ,medicine.disease_cause ,01 natural sciences ,Biochemistry ,Fluorescence ,In vitro ,0104 chemical sciences ,Sulfonamide ,chemistry.chemical_compound ,Thiomorpholine ,chemistry ,Morpholine ,Biophysics ,medicine ,Moiety ,Physical and Theoretical Chemistry ,0210 nano-technology ,Oxidative stress - Abstract
Two naphthalimide-based fluorescent probes containing a thiomorpholine (Np-NS) or a sulfoxide-morpholine (Np-NSO) component are reported. The morpholine unit of non-fluorescent Np-NS and Np-NSO can transform into sulphone-morpholine and be accompanied by blue fluorescence upon oxidative stress, ascribed to the formation of sulphone-morpholine on probes. This sensing behavior displays that they can selectively respond to glutathione to generate a green emission by a sulfonamide-based detection moiety both in vitro and in living cells. Interestingly, the different oxidation states of a sulphur atom on a thiomorpholine ring can be utilized to regulate responsiveness of these probes towards glutathione. Such an oxidation strategy would provide a possibility for enhancing the response rate.
- Published
- 2018
41. Novel thiomorpholine tethered isatin hydrazones as potential inhibitors of resistant Mycobacterium tuberculosis
- Author
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Vishal Kumar, Mavela Cleopus Mahlalela, Balakumar Chandrasekaran, Srinivas Reddy Merugu, Sanjeev Dhawan, Sivanandhan Karunanidhi, Harun M. Patel, Francis Kayamba, Rajshekhar Karpoormath, and Babita Kushwaha
- Subjects
Isatin ,Cell Survival ,Stereochemistry ,Morpholines ,Antitubercular Agents ,Microbial Sensitivity Tests ,01 natural sciences ,Biochemistry ,DNA gyrase ,Mycobacterium tuberculosis ,Structure-Activity Relationship ,chemistry.chemical_compound ,Drug Resistance, Multiple, Bacterial ,Drug Discovery ,Humans ,Molecular Biology ,IC50 ,ADME ,Binding Sites ,Strain (chemistry) ,biology ,010405 organic chemistry ,Organic Chemistry ,Hydrazones ,bacterial infections and mycoses ,biology.organism_classification ,0104 chemical sciences ,Molecular Docking Simulation ,010404 medicinal & biomolecular chemistry ,Thiomorpholine ,chemistry ,DNA Gyrase ,Docking (molecular) ,Drug Design ,Rifampin ,Half-Life - Abstract
Novel chemotherapeutic agents against multidrug resistant-tuberculosis (MDR-TB) are urgently needed at this juncture to save the life of TB-infected patients. In this work, we have synthesized and characterized novel isatin hydrazones 4(a-o) and their thiomorpholine tethered analogues 5(a-o). All the synthesized compounds were initially screened for their anti-mycobacterial activity against the H37Rv strain of Mycobacterium tuberculosis (MTB) under level-I testing. Remarkably, five compounds 4f, 4h, 4n, 5f and 5m (IC50 = 1.9 µM to 9.8 µM) were found to be most active, with 4f (IC50 = 1.9 µM) indicating highest inhibition of H37Rv. These compounds were further evaluated at level-II testing against the five drug-resistant strains such as isoniazid-resistant strains (INH-R1 and INH-R2), rifampicin-resistant strains (RIF-R1 and RIF-R2) and fluoroquinolone-resistant strain (FQ-R1) of MTB. Interestingly, 4f and 5f emerged as the most potent compounds with IC50 of 3.6 µM and 1.9 µM against RIF-R1 MTB strain, followed by INH-R1 MTB strain with IC50 of 3.5 µM and 3.4 µM, respectively. Against FQ-R1 MTB strain, the lead compounds 4f and 5f displayed excellent inhibition at IC50 5.9 µM and 4.9 µM, respectively indicating broad-spectrum of activity. Further, molecular docking, ADME pharmacokinetic and molecular dynamics simulations of the compounds were performed against the DNA gyrase B and obtained encouraging results.
- Published
- 2021
42. Evaluation of Inhibitory Activity In Silico of In-House Thiomorpholine Compounds between the ACE2 Receptor and S1 Subunit of SARS-CoV-2 Spike
- Author
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Nathan M. Markarian, Victor H. Vázquez-Valadez, Ma. Fernanda Jiménez-Cabiedes, Ingrid González-Tapia, Levon Abrahamyan, Enrique Angeles, Ana María Velázquez-Sánchez, Yoshio A. Alarcón-López, Alejandro Hernández-Serda, Laura Carreño-Vargas, Pablo A. Martínez-Soriano, Pablo Aguirre-Vidal, Miguel Lugo Álvarez, and Andrea Espejel-Fuentes
- Subjects
Microbiology (medical) ,Protein subunit ,In silico ,Biology ,Pharmacology ,010402 general chemistry ,medicine.disease_cause ,Inhibitory postsynaptic potential ,01 natural sciences ,Article ,thiomorpholine derivatives ,03 medical and health sciences ,chemistry.chemical_compound ,antivirals ,medicine ,Immunology and Allergy ,Receptor ,Molecular Biology ,030304 developmental biology ,Coronavirus ,0303 health sciences ,General Immunology and Microbiology ,SARS-CoV-2 ,Angiotensin-converting enzyme ,spike ,0104 chemical sciences ,3. Good health ,Infectious Diseases ,Thiomorpholine ,chemistry ,biology.protein ,Medicine ,Spike (software development) - Abstract
At the end of 2019, the world was struck by the COVID-19 pandemic, which resulted in dire repercussions of unimaginable proportions. From the beginning, the international scientific community employed several strategies to tackle the spread of this disease. Most notably, these consisted of the development of a COVID-19 vaccine and the discovery of antiviral agents through the repositioning of already known drugs with methods such as de novo design. Previously, methylthiomorphic compounds, designed by our group as antihypertensive agents, have been shown to display an affinity with the ACE2 (angiotensin converting enzyme) receptor, a key mechanism required for SARS-CoV-2 (severe acute respiratory syndrome coronavirus 2) entry into target cells. Therefore, the objective of this work consists of evaluating, in silico, the inhibitory activity of these compounds between the ACE2 receptor and the S1 subunit of the SARS-CoV-2 spike protein. Supported by the advances of different research groups on the structure of the coronavirus spike and the interaction of the latter with its receptor, ACE2, we carried out a computational study that examined the effect of in-house designed compounds on the inhibition of said interaction. Our results indicate that the polyphenol LQM322 is one of the candidates that should be considered as a possible anti-COVID-19 agent.
- Published
- 2021
43. Synthesis and antischistosomal activity of linker‐ and thiophene‐modified biaryl alkyl carboxylic acid derivatives
- Author
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Arnold Grünweller, Christoph G. Grevelding, Martin Schlitzer, Simone Haeberlein, Alejandra M. Peter Ventura, Leonie Konopka, and Wiebke Obermann
- Subjects
Male ,Sulfonyl ,chemistry.chemical_classification ,Carboxylic acid ,Carboxylic Acids ,Pharmaceutical Science ,Thiophenes ,Amides ,Medicinal chemistry ,Schistosomicides ,Structure-Activity Relationship ,chemistry.chemical_compound ,Piperazine ,Thiomorpholine ,chemistry ,Morpholine ,Drug Discovery ,Thiophene ,Animals ,Schistosoma ,Schistosomiasis ,Structure–activity relationship ,Female ,Linker - Abstract
Schistosomiasis is a neglected tropical disease caused by blood flukes of the genus Schistosoma and causes severe morbidity in infected patients. In 2018, 290.8 million people required treatment, and 200,000 deaths are reported per year. Treatment of this disease depends on a single drug, praziquantel (PZQ). However, in the past few years, reduced sensitivity of the parasites toward PZQ has been reported. Therefore, there is an urgent need for new drugs against this disease. In the past few years, we have focused on a new substance class called biaryl alkyl carboxylic acid derivatives, which showed promising antischistosomal activity in vitro. Structure-activity relationship (SAR) studies of the carboxylic acid moiety led to three promising carboxylic amides (morpholine, thiomorpholine, and methyl sulfonyl piperazine) with an antischistosomal activity down to 10 µM (morpholine derivative) and no cytotoxicity up to 100 µM. Here, we show our continued work on this substance class. We investigated, in extended SAR studies, whether modification of the linker and the thiophene ring could improve the antischistosomal activity. We found that the exchange of the alkyl linker by a pentadienyl or benzyl linker was tolerated and led to similar antischistosomal effects, whereas the exchange of the thiophene ring was not tolerated. Our data suggest that the thiophene ring is important for the antischistosomal activity of this compound class.
- Published
- 2021
44. Selective, stoichiometric and fast-response fluorescent probe based on 7-nitrobenz-2-oxa-1,3-diazole fluorophore for hypochlorous acid detection
- Author
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Marcin Szala, Radosław Podsiadły, Karolina Pierzchała, Radosław Michalski, Przemysław Siarkiewicz, Jaroslaw Romanski, Daniel Słowiński, Aleksandra Grzelakowska, and Małgorzata Świerczyńska
- Subjects
Fluorophore ,Hypochlorous acid ,Process Chemistry and Technology ,General Chemical Engineering ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,Fluorescence ,0104 chemical sciences ,Sulfone ,chemistry.chemical_compound ,Thiomorpholine ,chemistry ,Diazole ,0210 nano-technology ,Hydrogen peroxide ,Peroxynitrite - Abstract
A new selective probe containing the thiomorpholine unit (TM) was synthesized and examined for the fluorescence-based detection of hypochlorous acid (HOCl). Connection of TM with the fluorophore, 7-nitrobenz-2-oxa-1,3-diazole (NBD) effectively suppresses NBD fluorescence, whereas a HOCl-induced oxidation of TM to its S-oxide turns on a green emission. HPLC analysis shows that the reaction is stoichiometric and no sulfone is formed. Moreover, neither hydrogen peroxide nor peroxynitrite are able to oxidize the probe. Experimental data indicates that NBD-TM probe can be used to detect HOCl generated by myeloperoxidase (MPO). Presented results may be helpful in developing a novel class of fluorescent and luminogenic probes for the imaging of HOCl.
- Published
- 2021
45. Erratum to: Reaction of 4-Halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with Morpholine and Thiomorpholine Synthesis and Antimicrobial Activity
- Author
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Sergey V. Fedoseev and Oleg V. Ershov
- Subjects
chemistry.chemical_compound ,Thiomorpholine ,chemistry ,Morpholine ,Organic Chemistry ,Organic chemistry ,Halo ,Antimicrobial - Published
- 2021
46. Synthesis of novel N-, S-substituted-polyhalo-1, 3-butadienes and crystal structure of dibutadienyl homopiperazine.
- Author
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DENIZ, NAHIDE and IBIS, CEMIL
- Subjects
- *
BUTADIENE synthesis , *CRYSTAL structure , *PIPERAZINE , *NUCLEAR magnetic resonance spectroscopy , *HETEROCYCLIC compounds , *CHEMICAL precursors , *THIOLS - Abstract
Polyhalogenated-2-nitro-1, 3-butadienes are important synthetic precursors for a variety of polyfunctionalized bioactive heterocycles. Herein, we report the reactions of 1, 1, 3, 4, 4-pentachloro-2-nitro-1, 3-butadiene 1 and 4-bromo-1, 1, 3, 4-tetrachloro-2-nitro-1, 3-butadiene 2 with amino and thiol containing nucleophiles to obtain highly functionalized (E)-polyhalodiene-2-nitro-1, 3-butadiene derivatives. Most of these reactions were found to be highly selective resulting in good to high yields of the products. All new compounds have been characterized by nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS) and Fourier transform infrared spectroscopy (FT-IR) spectroscopic data. Single crystal X-ray structure analysis of compound 8c is reported. [Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]
- Published
- 2013
- Full Text
- View/download PDF
47. SnAP Reagents for the Transformation of Aldehydes into Substituted Thiomorpholines-An Alternative to Cross-Coupling with Saturated Heterocycles.
- Author
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Vo, Cam ‐ Van T., Mikutis, Gediminas, and Bode, Jeffrey W.
- Abstract
Die Umwandlung von Aldehyden in N ‐ unsubstituierte 3 ‐ Thiomorpholine bildet eine einfache Alternative zu metallkatalysierten Kreuzkupplungen, die zur Funktionalisierung gesättigter N ‐ Heterocyclen im Allgemeinen ungeeignet sind. Eine kupfervermittelte radikalische Cyclisierung ist der Schlüssel für die milden Bedingungen, die hohe Verträglichkeit mit funktionellen Gruppen und den großen Substratbereich, den diese Reagentien bieten. [ABSTRACT FROM AUTHOR]
- Published
- 2013
- Full Text
- View/download PDF
48. Synthesis of 4-chloro-2-(thiomorpholin-4-ylmethyl)phenol
- Author
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O. Olvera-Neria, R. López-Castañares, R. Hernández, A. Ramírez, L. Martínez, I. Martínez, I. Menconi, A. Pecina, A. Valencia, R. González, L. Torres, A. Ma. Velázquez, and E. Angeles
- Subjects
phenol ,thiomorpholine ,Inorganic chemistry ,QD146-197 - Abstract
n/a
- Published
- 2005
- Full Text
- View/download PDF
49. Distinct rhodamine B derivatives exhibiting dual effect of anticancer activity and fluorescence property
- Author
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Sivaganesh Bommi, Subbalakshmi Jayanty, Tarun Patel, Balaram Ghosh, Himabindu Battula, and Yamini Bobde
- Subjects
chemistry.chemical_classification ,010405 organic chemistry ,Carboxylic acid ,Rhodamine B amides ,Bandgap ,Cancer cell imaging agents ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Fluorescence ,Anticancer activity ,0104 chemical sciences ,Chemistry ,chemistry.chemical_compound ,Thiomorpholine ,chemistry ,Morpholine ,Amide ,Fluorescent probes ,Rhodamine B ,Proton NMR ,Amine gas treating ,QD1-999 ,CT-DNA interaction - Abstract
Design and application of novel Rhodamine B amide derivatives achieved especially with simple secondary amines, and furthermore exhibiting fluorescence property and anticancer activity is not reported elsewhere. Further functionalization of rhodamine B at the carboxylic acid group with selected secondary amines generated amides, avoiding cyclization and simultaneously sustaining fluorescence. Currently, we have designed and developed three well defined novel rhodamine B amide derivatives by reacting rhodamine B (RHB) with thiomorpholine, bis-(2-chloroethyl) amine and morpholine (the side chains of several anticancer drugs) via rhodamine B acid chloride which resulted in fluorophores namely rhodamine B thiomorpholine amide (1), rhodamine B bis(2-chloroethyl)amine amide (2) and rhodamine B morpholine amide (3). All the three RHB amides were thoroughly characterized using analytical techniques like FT-IR, Mass, 1H NMR, 13C NMR spectroscopy and HPLC. Obtained compounds displayed molecular material attributes as well as anticancer activity. The wavelength of maximum absorption and emission of solutions occurred at ~560 nm and ~583 nm. Quantum yields (Φf = 0.40) and average fluorescence decay (~1.60 ns) of amides was comparable to RHB (1.72 ns). Optical bandgap of solids revealed semiconducting property (~ 2.9 eV). Acquired rhodamine B amides were found to be insensitive over a wide range of pH i.e. from 2 to 10 suggesting their plausible utility in biological labeling, moreover, showed potential anticancer activity against B16F10 (murine melanoma cells), MDA-MB231 (human breast cancer cells), A549 (human lung cancer cells) while they displayed less toxicity to normal HEK 293 (human embryonic kidney) cells. Interestingly, the cellular uptake study manifested that more quantity of the compound were taken up by the cancer cells compared to normal cells which indicate that these amides might become potential candidates to be developed as theranostic agents.
- Published
- 2021
50. New N,S-Substituted Nitrobutadienes from Mono(Arylthio)Substituted Nitrobutadienes.
- Author
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Ibis, Cemil and Yıldırım, Hatice
- Subjects
- *
BUTADIENE , *X-ray diffraction , *CRYSTAL whiskers , *DERIVATIZATION , *PIPERAZINE , *MOLECULAR models - Abstract
N,S-Substituted nitrobutadienes 3a-g were synthesized from the reaction of the thiosubstituted derivatives 1a-g with thiomorpholine 2. The N,S-substituted nitrobutadienes 5a-g were obtained from the reaction of the thiosubstituted butadienes 1a-g with N-diphenylmethyl piperazine 4. The structure of butadiene 3c was elucidated by single crystal X-ray diffraction. [ABSTRACT FROM AUTHOR]
- Published
- 2009
- Full Text
- View/download PDF
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