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The alkylation of (4-fluorophenyl)acetonitrile with dibrompentane and 2,2'-dichlorodiethyl ether gave the corresponding nitriles, which were reduced with lithium aluminium hydride to obtain [1-(4-fluorophenyl)cyclohexyl]- and [1-(4-fluorophenyl)tetrahydro-2H-pyran-4-yl]methanamines. Treatment of the latter products with aryloxymethyloxiranes substituted in the aromatic ring resulted in the synthesis of. Some of the synthesized aryloxypropanolamines were transformed into the corresponding oxazolidines under the action of formalin. [ABSTRACT FROM AUTHOR]

Abstract Oxazolidine derivatives (OxD) have been described as third-line antibiotics and antitumoral agents. The inclusion complexes based on cyclodextrin could improve the solubility and bioavailability of these compounds. A novel synthetic OxD was used, and its inclusion complexes were based on 2-hydroxy-beta-cyclodextrin (2-HPβCD). We conducted an in silico study to evaluate the interaction capacity between OxD and 2-HPβCD. Characterization studies were performed through scanning electron microscopy (SEM), Fourier-transformed infrared (FTIR), nuclear magnetic resonance spectroscopy (1H-NMR), X-ray diffraction (XRD), and thermal analyses. A kinetic study of the OxD was performed, including a cytotoxicity assay using peripheral blood mononuclear cells (PBMCs). The maximum increment of solubility was obtained at 70 mM OxD using 400 mM 2-HPβCD. SEM analyses and FTIR spectra indicated the formation of inclusion complexes. 1H-NMR presented chemical shifts that indicated 1:1 stoichiometry. Different thermal behaviors were obtained. The pharmacokinetic profile showed a short release time. Pure OxD and its inclusion complex did not exhibit cytotoxicity in PBMCs. In silico studies provided a foremost insight into the interactions between OxD and 2-HPβCD, including a higher solubility in water and an average releasing profile without toxicity in normal cells.

Abstract In the last decade, the number of transcatheter heart valve replacement for severe heart valve disease has increased exponentially. Although the bioprosthetic artificial heart valve (BHV) has similar fluid dynamics performance to the original heart valve compared with mechanical heart valve so that there is no need to take long-term anticoagulant drugs to prevent thromboembolism, transcatheter BHV replacement are still at risk for thrombosis during the first few months according to the clinical data. However, the use of antithrombotic drugs can also increase the risk of bleeding. Therefore, it is particularly important to improve the anticoagulant properties for the BHV itself. In this work, a kind of non-glutaraldehyde cross-linked BHV material with excellent antithrombotic ability has been prepared from carboxylated oxazolidine treated porcine pericardium (consisting of collagen, elastin and glycoprotein) with the further graft of the anticoagulant heparin sodium via hydrophilic modified chitosan. Along with the similar mechanical properties and collagen stability comparable to the glutaraldehyde cross-linked porcine pericardium (PP), these functional non-glutaraldehyde cross-linked PPs exhibit better biocompatibility, promoted endothelial proliferation and superior anti-calcification ability. More importantly, excellent anticoagulant activity can be observed in the hematological experiments in vivo and in vitro. In summary, these excellent performances make these functional non-glutaraldehyde cross-linked PPs great potentialities in the BHV applications. Graphical abstract

The condensation of 2-alkylsulfanyl-substituted 2-en-4-ynals with N,N- and N,O-binucleophiles gives the corresponding 1,3-perhydrodiazines, 1,3-imidazolidines, and 1,3-oxazolidines with the original combination of substituents. [ABSTRACT FROM AUTHOR]

[Display omitted] • Preparation of amide functionalized polymer nanoparticles with Janus dumbbell-like morphology by emulsion copolymerization. • Physical modification of amide functionalized nanoparticles with oxazolidine. • Development of photoluminescence OLEDs based on oxazolidine polymer nanoparticles. • Printing of optical tags using of photoluminescent oxazolidine polymer nanoparticles. • Optical detection of the scratch by deposition of photoluminescent oxazolidine polymer nanoparticles on the surface. Photoluminescent polymer nanoparticles based on organic compounds are a new category of advanced materials with potential applications in various fields such as chemosensors, optical devices, drug-delivery systems, anticounterfeiting inks and bioimaging. Herein, amide functionalized copolymer nanoparticles with a particle size in the range of 42–139 nm were synthesized by emulsion copolymerization of methylmathacrylate (MMA) and methacrylamide (MAAm) with different concentrations in the range of 0–20 wt%. Afterward, the photoluminescent copolymer nanoparticles (PLCNPs) were prepared by physical modification of amide functionalized copolymer nanoparticles with 5 wt% of oxazolidine derivative (OXOH). Investigation of optical properties include of photoluminescence and UV–vis spectra displayed significant dependency of emission and absorbance bands to the local polarity or the concentration of the amide groups on the surface of the nanoparticles. Study of Commission Internationale de l'Eclairage (CIE) colorimetric diagrams for PLCNPs samples confirmed the results of photoluminescence and UV–vis spectra, which a logical shift in color of the photoluminescence emission was observed by an increase in the concentration of the amide groups. The PLCNPs samples have remarkable stability (in physical and optical properties) when applied on polar substrates such as polymer sheet and cellulose paper. Therefore, the PLCNPs samples were used for development of eco-friendly water based anticounterfeiting inks, photoluminescence organic light emitting diodes (OLEDs), and also the photodetection of scratches in a fast and facile manner. The printed security tags and hand-written phrases on cellulosic papers have orange fluorescent emission with maximum intensity because nanoscale size of particles, which reduced the light scattering and increased the accessible concentration of OXOH for light absorption. A coating of poly(vinyl alcohol) (PVA)/PLCNPs solution onto a blue LED (365 nm) was led to a change in the color of emission from blue to purple, because of the excitation of OXOH molecules at 365 nm with the subsequent emission of purple light. The photodetection of created scratch on polycarbonate sheet was carried out by spray of PLCNPs solution on sheet and then illumination with UV irradiation (365 nm). Developed water based PLCNPs samples have interesting optical properties, high stability on different surfaces and nanoscale particle size which are applicable in multiple applications such as eco-friendly photoluminescent inks for anticounterfeiting technologies, photoluminescence OLEDs, and also optical detector for monitoring of scratches on different substrates. [ABSTRACT FROM AUTHOR]

In many industries, safe organic inhibitors that are soluble in corrosive media, environmentally friendly, and effective need to be developed for protection against corrosion during descaling and steel pickling in dilute acids. In this work we describe, for the first time, the effects of 2-(nitromethylene) oxazolidine (OXA) and 2-(nitromethylene) imidazolidine (IMD) as inhibitors of the corrosion of SAE 1020 steel in 0.1 mol L−1 HCl aqueous solution. Electrochemical analyses showed that the IMD inhibitor was most effective, acting as a mixed type inhibitor. SEM analysis confirmed the electrochemical results, clearly showing the excellent corrosion inhibition effect of IMD. The corrosion inhibition was related to the protective film deposited on the surface, forming a layer that reduced the corrosion reactions. DFT calculations showed that donor and acceptor interactions between the heterocyclic nitrogen lone pair electrons and the vacant d orbitals of the metal surface atoms could explain the better corrosion inhibition values obtained for IMD. Finally, in addition to its efficiency, in silico toxicity predictions indicated that IMD could be considered environmentally friendly. [ABSTRACT FROM AUTHOR]

In the last decade, the number of transcatheter heart valve replacement for severe heart valve disease has increased exponentially. Although the bioprosthetic artificial heart valve (BHV) has similar fluid dynamics performance to the original heart valve compared with mechanical heart valve so that there is no need to take long-term anticoagulant drugs to prevent thromboembolism, transcatheter BHV replacement are still at risk for thrombosis during the first few months according to the clinical data. However, the use of antithrombotic drugs can also increase the risk of bleeding. Therefore, it is particularly important to improve the anticoagulant properties for the BHV itself. In this work, a kind of non-glutaraldehyde cross-linked BHV material with excellent antithrombotic ability has been prepared from carboxylated oxazolidine treated porcine pericardium (consisting of collagen, elastin and glycoprotein) with the further graft of the anticoagulant heparin sodium via hydrophilic modified chitosan. Along with the similar mechanical properties and collagen stability comparable to the glutaraldehyde cross-linked porcine pericardium (PP), these functional non-glutaraldehyde cross-linked PPs exhibit better biocompatibility, promoted endothelial proliferation and superior anti-calcification ability. More importantly, excellent anticoagulant activity can be observed in the hematological experiments in vivo and in vitro. In summary, these excellent performances make these functional non-glutaraldehyde cross-linked PPs great potentialities in the BHV applications. [ABSTRACT FROM AUTHOR]

Single-component moisture-cured polyurethane (SPU) possesses the merit of easy preparation and high curing efficiency but suffers from poor apparent properties, mechanical performance, and thermal stability. Herein, the authors employ isophorone diisocyanate (IPDI) and 2-isopropyl-3-hydroxyethyl-1, 3-oxazolidines (IHO) to synthesize oxazolidine (termed as IPDI-IHO) for the subsequent modification of SPU. The structure and composition of the synthesized SPU/IPDI-IHO composites are unraveled by ¹H and 13C NMR and FTIR spectroscopies. Apart from the curing properties of SPU/IPDI-IHO, the apparent properties, mechanical performance, thermal stability, and self-healing ability are evaluated. SEM and AFM characterizations reveal that IPDI-IHO incorporation significantly decreased the number of bubbles and thus reduce the SPU-based sample surface roughness. The thermal stability of SPU is notably improved after IPDI-IHO modification. The tensile strength and elongation at break also increases from 830 to 3710 kPa and from 210% to 600%, respectively, due to IPDI-IHO inclusion, with the optimal mechanical properties achieved at the IPDI-IHO mass ratio of 8 wt%. Furthermore, the cracks intentionally cut for the SPU/IPDI-IHO sample can be self-healed at 60 °C. The ensemble of the performance enhancements suggests that the IPDI-IHO developed in this work opens up a new route to fabricate high-performance SPU and related polymeric materials. [ABSTRACT FROM AUTHOR]

In this paper, we report the synthesis of peptidomimetics containing oxazolidin-2-one and oxazolidine rings. The two of these heterocyclic peptidomimetics novel series were obtained from serine as starting material through an efficient intramolecular cyclization. In the case of oxazolidine, the formation of only one diastereoisomer was observed. [ABSTRACT FROM AUTHOR]

2‐(2‐Oxoalkylidene)‐1,3‐oxazolidine derivatives were synthesized in good to excellent yields regiospecifically through the catalyst‐free electrophilic ring expansion of N‐unprotected aziridines and the ketene C=O double bond of α‐oxoketenes, in situ generated from the microwave‐assisted Wolff rearrangement of 2‐diazo‐1,3‐diketones. The ring expansion predominantly underwent an SN1 process and the hydrogen bond decides the (E)‐configuration of products. [ABSTRACT FROM AUTHOR]

In the mol­ecular structure of the title compound, C20H21N3O7, the quinoline ring system is slightly bent, with a dihedral angle between the phenyl and the pyridine rings of 3.47 (7)°. In the crystal, corrugated layers of mol­ecules extending along the ab plane are generated by C—HO hydrogen bonds. The inter­molecular inter­actions were qu­anti­fied by Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are from HH (42.3%), HO/OH (34.5%) and HC/ CH (17.6%) contacts. Mol­ecular orbital calculations providing electron-density plots of the HOMO and LUMO as well as mol­ecular electrostatic potentials (MEP) were computed, both with the DFT/B3LYP/6–311 G++(d,p) basis set. A mol­ecular docking study between the title mol­ecule and the COVID-19 main protease (PDB ID: 6LU7) was performed, showing that it is a good agent because of its affinity and ability to adhere to the active sites of the protein. [ABSTRACT FROM AUTHOR]

Oxazolidine as a novel stimuli-chromic compound displays different colors, when physically incorporated into polymer nanoparticles containing different polar functional groups. These polymer inks could be used for fast and facile encryption of confidential cellulosic documents, such as paper currency, passport, and certificates. • Synthesis of highly fluorescent oxazolidine derivatives. • Incorporation of oxazolidine molecules to functionalized polymer nanoparticles. • Multi-color fluorescent polymer nanoparticles containing oxazolidine derivatives. • Development of anticounterfeiting and authentication systems and optical sensors based on fluorescent polymer nanoparticles. • Printing of security marks on cellulosic papers to increase safety in security documents. Counterfeiting of confidential documents has been a costly challenge for banks, companies, and customers. Encryption of invisible security marks, such as barcodes, quick response codes, and logos, in national or international confidential documents by high-security anticounterfeiting inks is the most significant solution for counterfeiting problems. Ecofriendly multi-color photoluminescent anticounterfeiting inks based on highly-fluorescent polymer nanoparticles functionalized with new oxazolidine derivatives were developed for the fast and facile encryption of security labels on cellulosic documents, such as paper currency, passport, and certificate. Depending on the polarity of functionalized polymer nanoparticles, a wide range of colors and fluorescence emissions were observed as a result of polar-polar interactions between the oxazolidine molecules and surface functional groups of the nanoparticles. The fluorescent polymer nanoparticles showed spherical, vesicular, and cauliflower-like morphologies resulted from different surface functional groups. Functional polymer nanoparticles displayed high stability and printability on cellulosic substrates due to hydrogen bonding interactions. The highly-fluorescent polymer nanoparticles were also used to prepare anticounterfeiting inks with different colors and fluorescence emissions. All the ecofriendly polymeric anticounterfeiting inks were loaded to stamps with specific marks, and then applied to different confidential documents. Printed labels displayed highly intense fluorescence emission in different colors (green, orange, pink, and purple depending on the matrix polarity) under UV irradiation (365 nm). These water-based multi-color fluorescent anticounterfeiting inks with highly intense, bright, and sensitive fluorescence emission have potential applications in encryption and authentication of security patterns. [ABSTRACT FROM AUTHOR]

Two derivatives of Iimidazolidin 4-one (IMID4) and Oxazolidin 5-one (OXAZ5), were investigated as corrosion inhibitors of corrosion carbon steel in sea water by employing the theoretical and experimental methods. The results revealed that they inhibit the corrosion process and their %IE followed the order: IMID4 (89.093%)  OXAZ5 (80.179%). The %IE obtained via theoretical and experimental methods were in a good agreement with each other. The thermodynamic parameters obtained by potentiometric polarization measurements have supported a physical adsorption mechanism which followed Langmuir adsorption isotherm. Quantum mechanical method of Density Functional Theory (DFT) of B3LYP with a level of 6-311++G (2d, 2p) were used to calculate the geometrical structure, physical properties and inhibition efficiency parameters, in vacuum and two solvents (DMSO and H2O), all calculated at the equilibrium geometry, and correlated with the experimental %IE. The local reactivity has been studied through Mulliken charges population analysis. The morphology of the surface changes of carbon steel were studied using SEM and AFM techniques. [ABSTRACT FROM AUTHOR]

A series of reactions between an oxazolidine ligand 2-(2-(pyridin-2-yl)oxazolidin-3-yl)-N-(pyridin-2-ylmethylene)ethanamine (POPME) and CdX2 (X = Cl, Br, I) salts with different M:L molar ratios (1:1 and 2:1) is experimentally studied to determine the most stable product of these reactions. All products are characterized by the elemental analysis, FTIR, Raman, and 1H NMR spectroscopy, and single crystal X-ray diffraction. Examinations reveal that only one product is formed from 1:1 and 2:1 M:L reactions between each cadmium(II) halide with POPME. The thermodynamic stability and charge distribution patterns of the compound containing bromide are analyzed by DFT and NBO. [ABSTRACT FROM AUTHOR]

The commitment to sustainable development has been one of the main concerns of the world. In this sense, this work aims to develop a process for the application of oxazolidine in wet-white tanning and its viability for increasing the thermal stability of leather, reducing in this way the environmental impact of the tanning process. In order to achieve the higher shrinkage temperature, different parameters have been tested, such as time of reaction of the gluteraldehyde; the time of reaction and concentration of oxazolidine; the effect of synthetic and vegetable tannins at different conditions. Important conclusions were achieved, such as the direct relation between thermal stability and oxazolidine concentration, and the direct relation with the application time of tannins. The main result, a shrinkage temperature of 84.2°C, was obtained with a concentration of 6% w/w of oxazolidine and a contact time of 8 hours. Although the shrinkage temperature is high, there are still many improvements that must be done to achieve higher stability and then be exported to a pilot scale. [ABSTRACT FROM AUTHOR]

An asymmetric [3+2] cycloaddition of racemic vinyl epoxides with N‐benzothiazolimines has been presented under Pd‐catalysis. This transformation provides rapid access to highly functionalized oxazolidine scaffolds in generally good yields along with high stereoselectivities (up to 99% ee, 8.5 : 1 d.r.) under mild conditions. The use of chiral BINAP ligand enabled this asymmetric transformation with a broad substrate tolerance. [ABSTRACT FROM AUTHOR]

[Display omitted] Strategies that enable selective C N bond activation of tertiary amines provide one of the cornerstones of modern organic synthesis. Here we describe a palladium-catalyzed selective C N bond cleavage of N -propargyl 1,3-oxazolidines, providing an efficient approach to a diverse range of oxazolines in good to excellent yields. The reaction proceeds through a domino process of the alkyne-enabled 1,5-hydrogen transfer/C N bond activation. In this way, two kinds of oxazoline skeleton that tolerates a wide variety of functional groups were formed. [ABSTRACT FROM AUTHOR]

A new synthetic route to N-alkyl-2-acylazetidines was developed through a highly stereoselective addition of organolithiums to N-alkyl-2-oxazolinylazetidines followed by acidic hydrolysis of the resulting oxazolidine intermediates. This study revealed an unusual reactivity of the C=N bond of the oxazoline group when reacted with organolithiums in a non-polar solvent such as toluene. The observed reactivity has been explained considering the role of the nitrogen lone pair of the azetidine ring as well as of the oxazolinyl group in promoting a complexation of the organolithium, thus ending up with the addition to the C=N double bond. The high level of stereoselectivity in this addition is supported by DFT calculations and NMR investigations, and a model is proposed for the formation of the oxazolidine intermediates, that have been isolated and fully characterized. Upon acidic conditions, the oxazolidine moieties were readily converted into 2-acylazetidines. This synthetic approach has been applied for the preparation of highly enantioenriched 2-acylazetidines starting from chiral not racemic N-alkyl-2-oxazolinylazetidines.

The reaction between 2‐[2‐(aminoethyl)amino]ethanol and pyridine‐2‐carbaldehyde in a 1:2 molar ratio affords a mixture containing 2‐({2‐[(pyridin‐2‐ylmethylidene)amino]ethyl}amino)ethanol (PMAE) and 2‐[2‐(pyridin‐2‐yl)oxazolidin‐3‐yl]‐N‐(pyridin‐2‐ylmethylidene)ethanamine (POPME). Treatment of this mixture with copper(II) chloride or cadmium(II) chloride gave trichlorido[(2‐hydroxyethyl)({2‐[(pyridin‐2‐ylmethylidene)amino]ethyl})azanium]copper(II) monohydrate, [Cu(C10H16N3O)Cl3]·H2O or [Cu(HPMAE)Cl3]·H2O, 1, and dichlorido{2‐[2‐(pyridin‐2‐yl)oxazolidin‐3‐yl]‐N‐(pyridin‐2‐ylmethylidene)ethanamine}cadmium(II), [CdCl2(C16H18N4O)] or [CdCl2(POPME)], 2, which were characterized by elemental analysis, FT–IR, Raman and 1H NMR spectroscopy and single‐crystal X‐ray diffraction. PMAE is potentially a tetradentate N3O‐donor ligand but coordinates to copper here as an N2 donor. In the structure of 1, the geometry around the Cu atom is distorted square pyramidal. In 2, the Cd atom has a distorted octahedral geometry. In addition to the hydrogen bonds, there are π–π stacking interactions between the pyridine rings in the crystal packing of 1 and 2. The ability of PMAE, POPME and 1 to interact with ten selected biomolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B‐DNA) was investigated by docking studies and compared with doxorubicin. [ABSTRACT FROM AUTHOR]

Abstract Carbon-heteoratom chemistry is a method of choice for rapid construction of complex molecules. In the recent decade, its various applications flourished thanks to the click chemistry approach. Herein, we use a combination of C-X bond formation reactions to complete the synthesis of 1,2,3-triazolyl spirooxazolidines, bearing the fluorenylmethoxycarbonyl (fmoc) substituent. Thanks to the application of 2D-NMR spectroscopic methods and a multilevel computational approach, including a medicinal chemistry – inspired conformational search, PM7 semiempirical and DFT-based geometry optimization finalized with DFT-GIAO NMR shielding constant calculation, we were able to investigate the conformational space and assign cis/trans configuration in complex NMR spectra. For the obtained fmoc derivatives we recorded UV-VIS absorption and emission spectra. The obtained compounds contain pharmacophoric groups characteristic for endocannabinoid system modulators- CB1 receptor ligands or FAAH inhibitors. Graphical abstract Image 1 Highlights • An efficient synthetic pathway towards novel spirooxazolidine derivatives. • PM7 semiempirical studies explored large conformational space. • 1D and 2D NMR combined with DFT allowed to explain complex spectra. • UV-VIS absorption and emission spectra were recorded. • NOESY spectra indicated dimer formation. [ABSTRACT FROM AUTHOR]

The first organocatalytic asymmetric synthesis of 2,5‐disubstituted oxazolidines has been developed via hemiaminal formation between alkyl aldehydes and N‐tosyl aminomethyl enones followed by intramolecular oxa‐Michael reaction. Quinine derived bifunctional squaramide catalyst was found to be efficient for this reaction and a variety of alkyl aldehydes and N‐tosyl aminomethyl enones were employed. [ABSTRACT FROM AUTHOR]

Graphical abstract Existence of an extra methyl group induced the different chelating mode, therefore, several structurally different palladium imine and oxazolidine complexes were obtained. Investigation of the equilibrium between imine and oxazolidine complexes were carried out by DFT method which proved that the oxazolidine is more stable than imine compound. Abstract Reaction of 2-pyridinecarboxaldehyde with l -Alaninol (as a chiral amine) or 2-amino-2-methyl-1-propanol (AMP) in the presence of PdCl 2 produced the new and attractive palladium(II) complexes which were synthesized by in situ method. The presence of an extra methyl group in AMP other than l -Alaninol induced the different chelating mode and, therefore, several structurally different palladium complexes obtained. Correspondingly, the chiral amine with PdCl 2 produced the imine product, (Iminol (1)), and an oxazolidine compound (Imizol (1′)) as minor product. Also, the use of AMP in formation of palladium complexes led to the synthesis of imine (Ampynol (2)) and oxazolidine (Ampyzol (3)) complexes. Besides utilizing of crystallization technique for the separation of the isomers, elemental analysis (CHN), FT-IR, 1H and 13C NMR spectroscopies were used for characterization of the synthesized compounds. In addition, structures of palladium complexes Iminol and Ampyzol were identified by single crystal X-ray diffraction method and investigation of the equilibrium between imine and oxazolidine complexes were carried out by DFT method. The in vitro studies revealed that the compounds have considerable cytotoxicity against human MCF-7 and HeLa cancer cell lines. [ABSTRACT FROM AUTHOR]

A method for the formal β-functionalization of aliphatic ketones via a palladium-catalyzed sp3 C–H activation pathway is reported. An N,O-ketal directs an aliphatic C–H carbonylation to form γ-lactams which upon hydrolysis generate γ-keto carboxylic acids. This C–C bond-forming reaction is tolerant of a range of functional groups, enabling the synthesis of a range of synthetically important building blocks. Furthermore, the concepts underlying this transformation have also enabled the development of a related C–H alkenylation process to highly functionalised heterocycles. [ABSTRACT FROM AUTHOR]

A simple and efficient method for the synthesis of benzoxazolidines from the reaction of sulfonamidoalcohol and vinyl acetate was reported. The Ni‐catalyzed deacylation of vinyl acetate results in O‐alkenylated intermediate, which subsequently undergoes intramolecular annulation to afford C2‐alkylated benzoxazolidines. Scope of this method was also extended for the synthesis of other heterocycles of this class such as oxazolidine, benzoxazinolidine and benzimidazolidine. Halofunctionalization was also performed in‐situ in a sequential fashion in the presence of a halogen source. Most importantly, this reaction operates under ligand‐free conditions by using a bench‐top catalyst and does not require any inert atmosphere or dry solvent or any expensive terminal oxidant. An efficient and simple method for the preparation of benzoxazolidines, benzoxazinolidine and benzimidazolidine using bench‐top nickel catalyst under ligand‐free conditions has been reported. [ABSTRACT FROM AUTHOR]

In this work, the 2-(2-(pyridin-2-yl)oxazolidin-3-yl)ethanol (AEPC) ligand was prepared under solvent free conditions using ultrasonic irradiation, before reaction with a Cu(NO3)2/KSCN mixture, CuCl2 and CuI, the products of which were characterized by elemental analysis, UV-Vis, FT-IR spectroscopy and single-crystal X-ray diffraction. The X-ray analyses results revealed that AEPC, after reactions with the three copper(I/II) halides, gave structures ([Cu(DEA)Cl2] (2), DEA = diethanolamine, [Cu(BHEG)2] (3), BHEG = bis(2-hydroxyethyl)glycinato); however, it retains its structure on treatment with Cu(NO3)2/KSCN mixture ([Cu(AEPC)(NCS)2] (1)). The geometrical parameters for the complexes were compared with the Cambridge Structural Database (CSD) and coordination modes for thiocyanate ion were extracted. In the crystal structure of 1, the copper ion has a distorted square-pyramidal geometry and a CuNpyN2NCSNtertOalc environment in which the AEPC acts as NN'O-donor in a facial coordination mode. In the crystal structure of 2, the copper ion has a Cu(Nsec)(Oalc)2Cl2 environment and distorted square-pyramidal geometry in which the DEA ligand is coordinated as a mer-NO2-donor. The copper ion in 3 has a CuN2O4 environment and distorted octahedral geometry. The ability of these compounds to interact with the nine biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS and Top II) was investigated by Docking calculations and compared with that of doxorubicin. The thermodynamic stability of 1 and its isomer and also charge distribution patterns were studied by DFT and NBO analysis, respectively. [ABSTRACT FROM AUTHOR]

of hydrazones (N3- N10) were synthesized from the reaction of compound (N2) with various substituted benzaldehydes (aceto phenone) gave hydrazone compounds(N3-N10).Substituted compounds(N11-N12) , compound (N13) , compounds(N14-N16) ,compounds (N17-N18),Were synthesized from cyclization of hydrazones (N3- N10) using chloro acetic acid or tri chloro acetic acid or thio glycolic acid or chloro acetyl chloride respectively. The synthesized compounds were identified according to their physical properties, spectroscopic data (IR and1H- NMR) in addition to systematic identification of some active functional groups in these compounds. This the research includes synthesis of some new derivatives of 2-mercapto benzimidazole (N1), the compound (N1), prepared by reaction of o-phenylene diamine with carbon disulfide in alcoholic potassium hydroxide. Then the compound (N1) was treated with hydrazine hydrate in ethanol to give 2-hydrazinobenzimidazole ( N2).A Number

Reactions of acetylene glycidyl ethers with butylamine and ethylene diamine lead to the oxirane ring opening according to the Krasusky rule with the formation of acetylene aminoalcohols. In reaction with thiourea the oxygen atom in the ring is replaced by sulfur leading to the corresponding thiiranes in a high yield. The synthesized compounds possess high antimicrobial activity. [ABSTRACT FROM AUTHOR]

Four oxazolidine compounds OX1-OX4 were prepared. Their structures were characterized using Fourier transform infrared spectra, ¹H-NMR, 13C-NMR, and ESI-MS. The hydrolysis kinetics research of oxazolidines suggested that the hydrolysis of oxazolidine followed the first-order reaction. The gap of the ground energies between the open- and closed-ring was calculated using Gaussian software, which indicated that the stability of the open-ring system of OX1 was the best. Then, the obtained oxazolidines were applied to single-component polyurethane (SPU) and filler CaCO3 was added to investigate the effect of the two above on the properties of SPU. The results show that the pore size and the number of bubbles produced in the SPU decreased with the increase of the rate of hydrolysis of the added oxazolidine, and the bondability of the polyurethane was better. With the increase of CaCO3 content, the polyurethane surface became smoother and the bond strength was stronger. [ABSTRACT FROM AUTHOR]

Herein we report the straightforward preparation of novel conformationally-restricted steroids from trans -androsterone and estrone, decorated with spiranic oxazolidin-2-one or 2-aminooxazoline motifs at C-17 as potential antiproliferative agents. Such unprecedented pharmacophores were accessed using an aminomethylalcohol derivative at C-17 as the key intermediate; reaction of such functionality with triphosgene, or conversion into N-substituted thioureas, followed by an intramolecular cyclodesulfurization reaction promoted by yellow HgO, furnished such spirocycles in excellent yields. Title compounds were tested in vitro against a panel of six human tumor cell lines, named A549 (non-small cell lung), HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon), and the results were compared with steroidal chemotherapeutic agents (abiraterone and galeterone); the A-ring of the steroidal backbone, the nature of the heterocycle and the N-substituents proved to be essential motifs for establishing structure-activity relationships concerning not only the potency but also the selectivity against tumor cell lines. Estrone derivatives, particularly those bearing a spiranic 2-aminooxazoline scaffold were found to be the most active compounds, with GI 50 values ranging from the low micromolar to the submicromolar level (0.34–1.5 μM). Noteworthy, the lead compounds showed a remarkable increase in activity against the resistant cancer cell lines (T-47D and WiDr) compared to the anticancer reference drugs (up to 120-fold). [ABSTRACT FROM AUTHOR]

Two binuclear complexes,fac-[Cd2(AEPC)2(μ-Cl)2Cl2] (1) and [Hg2(AEPC)2(μ-Cl)2Cl2] (2), of 2-(2-(pyridin-2-yl)oxazolidin-3-yl)ethanol (AEPC) were prepared and identified by elemental analysis, FT-IR,1H NMR spectroscopies, and single-crystal X-ray diffraction. All coordination modes of 2-(pyridin-2-yl)oxazolidine derivatives were studied by analysis of the Cambridge Structural Database (CSD) for determination of coordination behaviors of the AEPC ligand with metals. In the crystal structure of1, the cadmium ion has a distorted octahedral geometry and CdN2OCl3environment in which each ligand acts as an NN′O-donor. In the crystal structure of2, the AEPC acts as NN′-donor toward the mercury ion to form a square-pyramidal geometry with three chloride ions. Each complex contains four chiral centers with a center of inversion and Cisymmetry. In the crystal networks of the complexes, the alcohol groups of the ligands participate in hydrogen bonding and form(28) and(44) hydrogen bond motifs (observed for1). In addition to the hydrogen bonds, the crystal network is stabilized byπ–πstacking interactions between pyridine rings of the AEPC ligands of adjacent complexes. The thermodynamic stability of the isolated complexes and their charge distribution patterns were studied by DFT and NBO analysis. [ABSTRACT FROM PUBLISHER]

A short and efficient strategy for the synthesis of (−)-cytoxazone, (−)-4- epi -cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydroxy methyl to methyl group increased the cellular immunity in in-vitro cultures. Changes in the stereochemistry of oxazolidine haven't influenced the biological activity. [ABSTRACT FROM AUTHOR]

A facile and convergent approach has been developed for the stereoselective construction of biologically important polyhydroxylated 2-acyl indolizidine framework using aza-Cope rearrangement-Mannich cyclization as a key step. The generality of this methodology is demonstrated with various lactol-tosylates derived from carbohydrates. The presented method provides an easy access to indolizidine- and tetrahydroindolizine-based iminosugar derivatives in good yields. [ABSTRACT FROM AUTHOR]

[Display omitted] • Synthesis of amphiphilic polymer nanoparticles containing amide functionality by emulsion polymerization. • Physical modification of anisotropic Janus polymer nanoparticles with oxazolidine. • Development of a fast and facile method for designing OLEDs with photoluminescence emission. • Using photoluminescent polymer nanoparticles as water-based anticounterfeiting inks for printing of optical tags. • A portable optical sensor for photodetection of the scratch by deposition on the surface. In this study, a new category of amphiphilic nanoparticles based on random copolymers was prepared by polymerization of the methyl methacrylate (MMA) with methacrylamide (MAAm) in emulsion media to develop functionalized nanoparticles containing amide polar groups in different concentrations, and also the size of nanoparticles is in the range of 47–145 nm. Subsequently, the physical modification of amide groups on the surface of functionalized amphiphilic nanoparticles by using oxazolidine derivative (OXOH) with a concentration of 5 wt% led to the development of photoluminescent copolymer nanoparticles (PLCNPs). The MAAm monomer was used to functionalize polymer nanoparticles with amide groups acting as electron donor groups for oxazolidine molecules and their stability on the surface of the polymer nanoparticles by hydrogen bonding. To investigate of optical properties, the PLCNPs samples containing different concentrations of amide groups (0–20 wt%) were studied by photoluminescence and UV–Vis spectroscopy. Obtained results indicate that the emission and absorbance bands (intensity and wavelength) can be influenced significantly by the concentration of amide groups located on the surface of amphiphilic nanoparticles, and most importantly the local polarity. Investigation of the color change of photoluminescence emission for PLCNPs samples as a function of amide group concentration by CIE colorimetric diagrams displayed regular shifts in color position by the increase of local polarity, which observed color shifts are in agreement with results of photoluminescence and UV–Vis spectra. It was observed that PLCNPs samples displayed suitable adhesion to the surface and stable optical properties when deposited or coated on substrates that have polar surfaces, such as thermoset/thermoplastic polymer sheets and also cellulose papers. Hence, the PLCNPs samples were used directly as the colloid solution to develop photoluminescence organic light emitting diodes, water-based and ecofriendly anticounterfeiting inks, and the portable sensor for the detection of artificially created scratches on the surface of the polycarbonate sheet by fluorescence imaging. The results displayed that printed security tags and encrypted information on cellulose papers have orange fluorescence emission with remarkable intensity because the size of latex particles is in the range of nanoscale (below 100 nm) which led to a reduction of light scattering and an increase of light absorption. In a new approach and for the first time, a solution of poly(vinyl alcohol) (PVA)/PLCNPs was deposited on LED (has blue light emission with a wavelength of 365 nm) to change the color of photoluminescence emission from blue to orange-purple by excitation of an organic photoluminescent polymer layer with UV light of LED (365 nm). On the other hand, the PLCNPs solutions were sprayed on the substrate to detect created scratches on the polycarbonate sheet under irradiation with UV light (365 nm) and fluorescence imaging. The advantages of developed water-based PLCNPs samples resulted in to use as an all-in-one nanomaterial in a different and wide range of applications, such as photoluminescent inks for ecofriendly anticounterfeiting technologies, photoluminescence OLEDs, and also a portable detector for optical visualization of scratches and micro-cracks on various substrates. [ABSTRACT FROM AUTHOR]