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The microwave spectrum of 2,4-dimethylpyrrole was investigated using a Fourier-transform microwave spectrometer in a supersonic expansion. Torsional splittings arising from two inequivalent methyl internal rotors in combination with hyperfine splittings due to the nuclear quadrupole coupling of the 14N nucleus were observed. The experiments were accompanied by quantum chemical calculations. A total of 1561 rotational lines were assigned and fitted in global fits using the programs XIAM and BELGI-Cs-2Tops-hyperfine, both achieved the measurement accuracy of 4 kHz. Local separate fits were also performed to verify the correctness of the assignment. Accurate experimental molecular and internal rotation parameters could be deduced and compared to the calculated ones. The barrier to internal rotation of the 2-methyl rotor was determined to be 277.830(26) cm−1, essentially the same as the value of about 280 cm−1 found for 2-methylpyrrole but lower than the value of 317 cm−1 found for 2,5-dimethylpyrrole. The torsional barrier value of the 4-methyl rotor is 262.210(27) cm−1, slightly higher than the value of 246 cm−1 found for 3-methylpyrrole. Benchmarking the rotational constants for 2,4- and 2,5-dimethylpyrrole revealed that the MP2/6-31G(d,p) level could be helpful to guide the assignment of microwave spectra of pyrrole derivatives. [ABSTRACT FROM AUTHOR]

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Comprehensive Summary: Indolizine is a nitrogen‐containing heterocycle with strong aromaticity, possessing a delocalized 10π‐electron system. Based on the indolizine scaffolds, numerous molecules with biological activity and organic functional materials have been synthesized. Since 2016, over 110 papers have been published on the synthesis of indolizine scaffolds, but the reviews on synthesizing indolizine scaffolds have been incomplete and not up‐to‐date. Herein, from the perspective of the structure of indolizine with the combination of pyrrole and pyridine ring, we focus on the construction of indolizine scaffolds through the diversity of starting substrates, including pyridine derivatives (N1‐substituted pyridinium salt derivatives, C2‐substituted pyridine derivatives, N1‐ and C2‐free substituted pyridine derivatives), pyrrole derivatives and unoriginal ring substrates. Furthermore, the corresponding reaction mechanisms of synthetic methodologies are also elaborated. Therefore, this review not only paves the way for indolizine synthesis but also provides insight into exploring new reaction modes for constructing nitrogen‐containing heterocycles. Key Scientists: Indolizine was discovered by Angeli in 1890 and first prepared by Scholtz in 1912 from α‐picoline and acetic anhydride. A general approach was developed by Chichibabin in 1927, that is of practical value for the preparation of 2‐alkyl‐ or 2‐arylindolizines. The Chichibabin reaction was the ring closure of quaternary pyridinium halides. At the begining of the 21st century, Basavaiah introduced a new dimension in the Baylis‐Hillman chemistry leading to a novel facile convenient methodology for synthesis of indolizine scaffolds in one‐pot operation. In 2010, Barluenga reported Cu(I)‐catalyzed regioselective [3+2] cyclization of unsubstituted pyridines toward alkenyldiazoacetates leading to functionalized indolizine derivatives, that was the first successful example of metal‐catalyzed cyclization of a π‐deficient heterocyclic system with alkenyldiazo compounds. In 2019 and 2022, Xi and Liu exploited the methods of non‐pyridine derivatives as starting materials to synthesize indolizines, respectively. In 2022, Guo developed an environmentally benign electrooxidative approach for constructing formyl‐ and acyl‐substituted indolizines. [ABSTRACT FROM AUTHOR]

We designed and synthesized two novel blue pyrrole derivatives, 2-(3-cyano-4-(4-(dibutylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (BAPCP) and 2-(3-cyano-4-(4-(dihexylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (HAPCP), as potential candidates for use in image sensor color filters. The properties of these new compounds were evaluated, focusing on their optical and thermal characteristics in solution and color filter film forms. The molar extinction coefficient values of BAPCP and HAPCP in solution were 6.03 × 104 and 6.91 × 104 L/mol·cm. The molar extinction coefficient of HAPCP was 4.5 times higher than that of the commercially used Disperse Blue 359. The synthesized compounds exhibited transmittance values that meet commercial requirements, with 88.6% at 450 nm and 0.73% at 530 nm. Both newly synthesized compounds met the decomposition temperature requirement of over 230 °C, which is necessary for the manufacturing process of image sensor color filters. The decomposition temperatures of both compounds were approximately 19 °C higher than that of Disperse Blue 359. When the thermal stability of color filter films for image sensors was evaluated, BAPCP demonstrated excellent optical properties before and after thermal stability testing, maintaining its characteristics in an optimized molecular form. Accordingly, BAPCP appears to have favorable potential as a blue colorant for image sensors, attributed to its superior optical and thermal stability characteristics. [ABSTRACT FROM AUTHOR]

Two novel copper-catalyzed cyclization reactions involving a remote propargylic substitution/cyclization/isomerization cascade are disclosed. Derivatives of the seldomly studied heterocycles thieno[2,3- c ]pyrrole and thieno[2,3- d ]pyridazine are conveniently synthesized in moderate to good yields from primary amines or arylhydrazines through [4+1] and [4+2] reactions, respectively. Preliminary mechanistic experiments corroborated the occurrence of the designed cascade reactions. [ABSTRACT FROM AUTHOR]

This study focused on investigating the synthesis of new spiropyrrole derivatives with high yields. The two nanocatalyst CuO/ZnO@Graphen Oxide nanocomposites (CuO/ZnO@GO NCs) and Ag/CuO/ZnO@Graphen Oxide (Ag@CuO/ZnO@GO NCs) were employed in a multicomponent reaction at room temperature to synthesize new compounds. The reaction involved isatins, N‐alkyl isatins, and ninhydrin as activated carbonyl compounds, ammonium acetate, ethyl 2‐arylamino‐4‐dioxo‐4‐arylbutanoates, hydrazonoyl chloride, or ethylbromopyruvate in water. Also, the catalytic activity of the green synthesized CuO/ZnO@GO and Ag@CuO/ZnO@GO was evaluated in the reduction of organic pollutants such as 4‐nitrophenol (4‐NP) in water at mild conditions. The results indicated that the biosynthesized MNCs have very high and effective catalytic activity for organic pollutants within a few seconds. The newly synthesized spiro compounds demonstrate antioxidant activity as a result of two assessment processes conducted by its NH group. In addition, the antibacterial activity of newly created spiro compounds was assessed using a disk distribution method, involving two types of Gram‐negative bacteria. These compounds were found to limit the growth of Gram‐positive bacteria as well. Also, to better understand the reaction mechanism, density functional theory (DFT)–based quantum chemical methods have been applied. The advantages of this technology encompass rapid response times, high product yields, and uncomplicated catalyst and product separation via simple procedures. [ABSTRACT FROM AUTHOR]

Pyrroles are a fundamental class of heterocyclic compounds that play a crucial role in many biologically active natural products and synthetic pharmaceuticals. Their unique electronic properties and structural versatility make them indispensable for the development of molecules with significant therapeutic potential. In this work, we introduce a novel approach to the formation of the pyrrole core, catalysed by L -proline, employing Paal–Knorr synthesis as the key transformation. This innovative method facilitates the efficient construction of the core structure while allowing for the introduction of diverse substituents, leading to the synthesis of over 20 highly functionalized pyrrole derivatives. Building upon this pyrrole core synthesis, we have extended our strategy to the construction of the pyrrolo[2,1-a]isoquinoline scaffold, an essential structural motif present in several alkaloids and pharmacologically active compounds. This scaffold is notable for its biological relevance, particularly in anti-cancer and anti-inflammatory applications. Our method showcases the versatility of the Paal–Knorr synthesis, enabling precise construction of the pyrrolo[2,1-a]isoquinoline core, starting from substituted chalcones. The synthetic route offers a reliable pathway for constructing complex heterocyclic structures, advancing our understanding of pyrrole and isoquinoline chemistry and providing valuable insights for the development of new therapeutic agents. [ABSTRACT FROM AUTHOR]

Nitrogen heterocycles are valuable structural elements in the molecules of antibacterial drugs approved and used to treat bacterial infections. Pyrrole is a five-atom heterocycle found in many natural compounds with biological activity, including antibacterial activity. Numerous compounds are being develop based on the pyrrole heterocycle as new potential antibacterial drugs. Due to the phenomenon of antibacterial resistance, there is a continuous need to create new effective antibacterials. In the scientific literature, we have identified the most relevant studies that aim to develop new compounds, such as pyrrole derivatives, that are proven to have antibacterial activity. Nature is an endless reservoir of inspiration for designing new compounds based on the structure of pyrrole heterocycles such as calcimycin, lynamycins, marinopyrroles, nargenicines, phallusialides, and others. However, many other synthetic compounds based on the pyrrole heterocycle have been developed and can be optimized in the future. The identified compounds were classified according to the type of chemical structure. The chemical structure–activity relationships, mechanisms of action, and antibacterial effectiveness of the most valuable compounds were highlighted. This review highlights scientific progress in designing new pyrrole-containing compounds and provides examples of lead compounds that can be successfully optimized further. [ABSTRACT FROM AUTHOR]

An unexpected route for the synthesis of pyrano [3,4-c] pyrrole derivatives has been reported via catalyst-free, three-component reaction of 1,3-dicarbonyl pyrazole, aromatic primary amines and fumaryl chloride. This novel cascade reaction sequence led to create two new rings and four new σ bonds containing two C–N, one C–C, and one C–O bond. The newly synthesized compounds were elucidated on the basis of their spectroscopic data (1H, 13C, 2D NMR, HRMS, IR) and additionally confirmed by single-crystal X-ray diffraction analysis. The molecular docking simulation was performed utilizing the AutoDock 4.2 program to predict the binding affinity of one derivative of the synthesized compounds to the target mitogen-activated protein kinase P38 (MAPK P38) and mitogen-activated protein kinase 14 (MAPK 14). [ABSTRACT FROM AUTHOR]

A base promoted oxidative [4+2] annulation of pyrrole‐2‐carbaldehyde derivatives with o‐hydroxyphenyl propargylamines for the synthesis of highly substituted indolizines has been developed. Using DBN as base, a broad range of 5,6,7‐trisubstituted indolizines have been prepared in good to excellent yields under mild conditions, and many useful functional groups can be tolerated. [ABSTRACT FROM AUTHOR]

ABSTRACT Nowadays, environmentally sustainable organic synthesis is demanding. In this context, nanoparticles are particularly interesting owing to their green synthesis aspects. Specifically, magnetic nanoparticles have been continuously utilized in organic synthesis for a decade. Among heterocycles, pyrrole and its analogs have a unique place due to its vast spectrum of applications. Derivatives of pyrrole help to find lead structures for new synthetic pharmaceutical compounds and other valuable compounds. Thus, magnetic nanoparticles accelerate organic chemists to develop pyrrole derivatives through green synthesis. Moreover, magnetic nanoparticles in pyrrole scaffold synthesis improve reaction efficiency and sustainability and create unique functional molecular hybrids for many scientific applications. This paper reviews the utilization of magnetic nanoparticles to afford a variety of valuable pyrrole derivatives, with a focus on their environmental friendliness. [ABSTRACT FROM AUTHOR]

Chlorfenapyr is a novel broad-spectrum insecticide derived from natural pyrrole derivatives produced by Streptomyces spp. It acts as a pro-insecticide and is metabolically converted to the active metabolite, tralopyril. Chlorfenapyr poisoning is known for its delayed neurological symptoms and high mortality. Unfortunately, information on the toxicokinetics, metabolism and tissue distribution of chlorfenapyr and tralopyril is still lacking. In this study, the metabolic profile, toxicokinetics and tissue distribution of chlorfenapyr and tralopyril after oral administration at a toxic dose in mice were investigated. Twenty metabolites were identified in plasma, urine and feces, which were mainly formed by dealkylation, oxidative dechlorination and reductive dechlorination. Toxicokinetic results showed that chlorfenapyr was rapidly converted to tralopyril after administration, and the in vivo half-life (t1/2), area under the curve (AUC) and peak concentration (Cmax) values of tralopyril were significantly higher than those of chlorfenapyr (P < 0.05). Tissue distribution experiments confirmed that the metabolite tralopyril had a longer half-life, a lower clearance and a wide distribution in different organs and tissues compared to chlorfenapyr. It was also able to cross the blood–brain barrier, suggesting a potential association with brain lesions. In addition, a sensitive and rapid LC–MS/MS analytical method was established for the detection of chlorfenapyr and tralopyril. In conclusion, this study provided valuable metabolic, toxicokinetic and tissue distribution information, contributing to future risk assessment and forensic identification in cases of chlorfenapyr poisoning. We recommend considering the assessment of tralopyril levels, which may be of greater therapeutic importance in the management of chlorfenapyr poisoning. [ABSTRACT FROM AUTHOR]

A new series of 1,2,3-triazole skeleton incorporated pyrrole derivatives (11a–j) were developed and their chemical structures were confirmed by analytical data. Further, the anticancer profile of these newly derived compounds 11a–j was assessed against four types of human cancer cell lines such as human breast cancer (MCF-7), lung cancer (A549), colon cancer (Colo-205) and ovarian cancer (A2780) by employing of the MTT method and was compared with etoposide used as a positive control. Most of the examined derivatives displayed moderate to good activity compared with the positive control. Among them, five compounds 11a, 11b, 11c, 11d, and 11e showed more potent activity. Particularly, compound 11a showed superior activity. [ABSTRACT FROM AUTHOR]

The article discusses the synthesis of new indeno[1,2-b]pyrroles and pyrrole-fused isocoumarins in aqueous media using a three-component domino reaction. These compounds have shown various biological activities, including antimicrobial properties. The study explores the feasibility of preparing these compounds, which are structurally similar to known antimicrobial agents, and evaluates their antibacterial activity against different strains. The results show promising antimicrobial activities, suggesting the potential of these compounds as novel antimicrobial agents. [Extracted from the article]

In recent years, nitrogen‐based ruthenium complexes have become an important material for dye‐sensitized solar cells and photo‐catalytic H2O and CO2 reduction research and applications, thanks to their charge transfer feature from the metal to the ligand. The electronic and spectral properties of such materials can be easily modified by changing the substituents and ligands. In this study, a new ruthenium (II) complex with N‐functionalized pyrrole derivative ([Ru(bpy)2(bpyCONHArPy)]+2 complex) was successfully synthesized and characterized. Its optical and electrochemical properties were studied by means of fluorescence, UV‐vis spectrometry, FTIR spectroscopy and cyclic voltammetry. These results were compared with that of its components (4‐(1H‐pyrrol‐1‐yl) aniline, N4,N4′‐bis(4‐(1H‐pyrrol‐1‐yl)phenyl)‐[2,2′‐bipyridine]‐4,4′‐dicarboxamide and ligand [Ru(bpy)3]+2). Related theoretical studies were also studied to find energy levels of complex. The present work is carried out to understand what chemical changes bring when combination of all the pieces of the puzzle into a chemical structure step by step. [ABSTRACT FROM AUTHOR]

Drawing inspiration from the structural resemblance between a natural product N-(3-carboxypropyl)-2-acetylpyrrole and phenylbutyric acid, a pioneer HDAC inhibitor evaluated in clinical trials, we embarked on the design and synthesis of a novel array of HDAC inhibitors containing an N-linked 2-acetylpyrrole cap by utilizing the pharmacophore fusion strategy. Among them, compound 20 exhibited potential inhibitory activity on HDAC1, and demonstrated notable potency against RPMI-8226 cells with an IC50 value of 2.89 ± 0.43 μM, which was better than chidamide (IC50 = 10.23 ± 1.02 μM). Western blot analysis and Annexin V-FTIC/propidium iodide (PI) staining showed that 20 could enhance the acetylation of histone H3, as well as remarkably induce apoptosis of RPMI-8226 cancer cells. The docking study highlighted the presence of a hydrogen bond between the carbonyl oxygen of the 2-acetylpyrrole cap group and Phe198 of the HDAC1 enzyme in 20, emphasizing the crucial role of introducing this natural product-inspired cap group. Molecular dynamics simulations showed that the docked complex had good conformational stability. The ADME parameters calculation showed that 20 possesses remarkable theoretical drug-likeness properties. Taken together, these results suggested that 20 is worthy of further exploration as a potential HDAC-targeted anticancer drug candidate. [ABSTRACT FROM AUTHOR]

A rapid practical new synthesis of multi-substituted pyrrole derivatives with high yields through a novel four-component reaction of sulfonyl azides, terminal alkynes, nitro compounds, and trichloroacetonitril is a remarkable achievement in organic chemistry. This strategy offers a direct and efficient route to access complex molecular structures from readily available starting materials. To expand the work, the reaction of the final product with sulfinate salt under simple conditions and room temperature, poly-substituted pyrroles with sulfone functional group are formed. The combination of available starting materials, catalytic systems, mild reaction conditions, and ease of purification procedures contributes to the attractiveness of this method for the synthesis of diverse multi-substituted pyrrole derivatives. [ABSTRACT FROM AUTHOR]

Herein, we report a new method for the synthesis of functionalized pyrrole and isoquinoline derivatives using isoxazole based precursors. The reaction proceeds through the ring opening and ring closing cascade mechanism (ROCC) to afford pyrrole or isoquinoline derivatives in good to excellent yields under very mild experimental conditions. Product outcome relies on the strategic placement of different substituents on the isoxazole moiety. The present method is also applicable to synthesize functionalized isoquinolone derivatives. [ABSTRACT FROM AUTHOR]

Copyright of China Pulp & Paper is the property of China Pulp & Paper Magazines Publisher and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

A ruthenium‐catalyzed reductive amination via asymmetric transfer hydrogenation (ATH) has been used to perform an efficient dynamic kinetic resolution (DKR) of N‐aryl 2‐formyl pyrroles decorated with a phosphine moiety positioned at the ortho' position. The strategy relies on the labilization of the stereogenic axis in the substrate facilitated by a transient Lewis acid‐base interaction (LABI) between the carbonyl carbon and the phosphorus center. The reaction features broad substrate scope of aliphatic amines and N‐aryl pyrrole scaffolds, and proceeds under very mild conditions to afford P,N atropisomers in good to high yields and excellent enantioselectivities (up to 99 % ee) for both diphenyl and dicyclohexylphosphino derivatives. [ABSTRACT FROM AUTHOR]

A synthetic strategy involving salicylaldehyde, 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF), and pyrrole has been developed to construct novel pyrrole-4H-chromene-embedded vinyl sulfonyl fluoride derivatives with exclusive regioselectivity. This method exhibits moderate to excellent yields (45–93%) and showcases a wide substrate scope with excellent functional group compatibility. Additionally, the resulting sulfonyl fluorides were further diversified via sulfur fluoride exchange (SuFEx) reactions to produce sulfonates and sulfonamides, which are valuable structural motifs in medicinal chemistry. [ABSTRACT FROM AUTHOR]

Arylethynyl‐substituted dipyrrolyldiketone BF2 complexes as anion‐responsive π‐electronic molecules exhibited characteristic electronic properties derived from conformation changes upon anion binding, which caused an increase in UV/vis absorption and associated two‐photon absorption. The anion complexes showed expanded planar regions assisted by intramolecular interactions, resulting in charge‐by‐charge ion‐pairing assemblies in the solid state. [ABSTRACT FROM AUTHOR]

Considering the complex pathogenesis of Alzheimer's disease (AD), the multi-target ligand strategy is expected to provide superior effects for the treatment of the neurological disease compared to the classic single target strategy. Thus, one novel pyrrole-based hydrazide (vh0) and four corresponding hydrazide–hydrazones (vh1-4) were synthesized by applying highly efficient MW-assisted synthetic protocols. The synthetic pathway provided excellent yields and reduced reaction times under microwave conditions compared to conventional heating. The biological assays indicated that most of the novel pyrroles are selective MAO-B inhibitors with IC50 in the nanomolar range (665 nM) and moderate AChE inhibitors. The best dual-acting MAO-B/AChE inhibitor (IC50 hMAOB–0.665 μM; IC50 eeAChE—4.145 μM) was the unsubstituted pyrrole-based hydrazide (vh0). Importantly, none of the novel molecules displayed hMAOA-blocking capacities. The radical-scavenging properties of the compounds were examined using DPPH and ABTS in vitro tests. Notably, the hydrazide vh0 demonstrated the best antioxidant activities. In addition, in silico simulations using molecular docking and MM/GBSA, targeting the AChE (PDB ID: 4EY6) and MAO-B (PDB: 2V5Z), were utilized to obtain active conformations and to optimize the most prominent dual inhibitor (vh0). The ADME and in vitro PAMPA studies demonstrated that vh0 could cross the blood–brain barrier, and it poses good lead-like properties. Moreover, the optimized molecular structures and the frontier molecular orbitals were examined via DFT studies at 6-311G basis set in the ground state. [ABSTRACT FROM AUTHOR]

Three 2,4‐diarylpyrroles were synthesized starting from 4‐nitrobutanones and the crystal structures of two derivatives were analysed. These are 4‐(4‐methoxyphenyl)‐2‐(thiophen‐2‐yl)‐1H‐pyrrole, C15H13NOS, and 3‐(4‐bromophenyl)‐2‐nitroso‐5‐phenyl‐1H‐pyrrole, C16H11BrN2O. Although pyrroles without substituents at the α‐position with respect to the N atom are very air sensitive and tend to polymerize, we succeeded in growing an adequate crystal for X‐ray diffraction analysis. Further derivatization using sodium nitrite afforded a nitrosyl pyrrole derivative, which crystallized in the triclinic space group P with Z = 6. Thus, herein we report the first crystal structure of a nitrosyl pyrrole. Interestingly, the co‐operative hydrogen bonds in this NO‐substituted pyrrole lead to a trimeric structure with bifurcated halogen bonds at the ends, forming a two‐dimensional (2D) layer with interstitial voids having a radius of 5 Å, similar to some reported macrocyclic porphyrins. [ABSTRACT FROM AUTHOR]

Pyrrole is a heterocyclic structure with diverse pharmacophores, enabling the creation of an extensive lead molecule library. Its broad range of pharmacological profiles has concerned significant global research interests. This review highlights recent advancements in pyrrole scaffolds, focusing on their structure active relationship and bioactivities. Pyrrole derivatives recognized for their biological activities, are promising scaffolds for developing antimicrobial, antimalarial, antiviral, antituberculosis, and enzyme‐inhibiting properties. Their unique anti‐inflammatory and antioxidant features have prompted the development of novel cardioprotective and neuroprotective compounds. The review aims to elucidate the SAR of pyrrole mimics, aiding future therapeutic developments. [ABSTRACT FROM AUTHOR]

In this study, Co3O4 nanoparticles were used as nanocatalyst for two different series of nitrogen-containing heterocyclic compounds, including pyrrole (Pyo) derivatives and pyrano [2, 3-c]pyrazole (Pya[2, 3-c]Pyz) derivatives. In the synthesis of derivatives, using 15 mol% and 10 mol% of the catalyst for Pyo derivatives and Pya[2, 3-c]Pyz derivatives, respectively, an efficiency between 83% and 96%, were observed. In addition, novel derivatives of Pyo and Pya[2,3- c]Pyz were synthesized and their structures were confirmed. In general, the advantages of using cobalt nanoparticles compared to previous reports include the synthesis of new derivatives, lower temperature used in the synthesis of derivatives, shorter synthesis time and high efficiency. The biological properties of the synthesized products, such as antibacterial, antifungal, and antioxidant properties, were tested and investigated. In antibacterial and antifungal tests, IZD, MIC, MBC, and MFC were measured and reported. In antioxidant activity, IC50 was calculated and reported. High reusability, green and environmentally friendly, synthesis of new derivatives and synthesis of products with higher efficiency and shorter time were the important benefits of using cobalt nanoparticles as a catalyst. In antioxidant tests, the IC50 for synthesized Pyo derivatives and Pya[2, 3-c] Pyz derivatives were between 12.2 and 13.71 μg/mL, and 16.18--17.75 μg/mL, respectively. In antimicrobial testes, the MIC for synthesized Pyo derivatives and Pya[2, 3-c]Pyz derivatives were between 2 and 4,096 μg/mL, and 2--2048 μg/mL, respectively. The results showed that the antioxidant property of Pyo derivatives were more than Pya[2, 3-c] Pyz derivatives, but the antimicrobial effect of Pya[2,3-c] Pyz derivatives were more than Pyo derivatives. The antioxidant results proved that the activity of Pyo derivatives and Pya[2, 3-c] Pyz derivatives does not depend on the substitutions of the derivatives and is close to each other. Therefore, based on this, a proposed mechanism for stability of DPPH by Pyo derivatives and Pya[2, 3-c] Pyz derivatives were suggested. Finally, based on the more stable resonance structures of Pyo derivatives, compared to Pya[2, 3-c] Pyz derivatives, its high antioxidant property was justified. Pya[2, 3-c] Pyz derivatives has two heterocyclic rings connected together pyrano and pyrazole, but Pyo derivatives has only one heterocyclic ring (pyrrole). So high antimicrobial property of Pya[2, 3-c] Pyz derivatives compared to Pyo derivatives can be attributed to having two bioactive heterocyclic rings. [ABSTRACT FROM AUTHOR]

A novel dithieno[3,2-b:2',3'-d]pyrrole (DTP) derivative, namely, 4-(4-(1H-pyrrol-1-yl)phenyl)-4H-dithieno[3,2-b:2',3'-d]pyrrole (DTP-Ph-Pyr) was synthesized, and its corresponding polymer (P(DTP-Ph-Pyr)) was successfully obtained via electrochemical polymerization. Electrochemical and optical properties of this novel polymer were discussed in detail. It was found that the polymer film also exhibited a reversible electrochromic behavior (orange color in the neutral state and blue color in the oxidized state) with a high optical contrast (52.5% at 950 nm) and coloration efficiency (123 cm2/C at 950 nm). Moreover, the electrochemical and optical properties of the polymer were compared with both its electrochromic P(DTP) analogues and its sister polymer structure, poly(1-(4-(1H-pyrrol-1-yl)phenyl)-2,5-di(thiophen-2-yl)-1H-pyrrole) (P(SNS-Ph-Pyr)), possessing same subunit. [ABSTRACT FROM AUTHOR]

This article discusses the synthesis of 5-amino-1H-pyrazole-4-carbonitriles using Ag/ZnO nanoparticles as a recyclable catalyst. The authors developed a one-pot procedure using environmentally friendly plant extracts to prepare the nanoparticles and optimized the reaction conditions to achieve high yields. The protocol proved to be effective for the synthesis of the desired compounds, which have various biological activities and are found in important drugs. The document also provides spectroscopic data for the synthesized compounds and acknowledges the institutions for support. [Extracted from the article]

Copyright of Al-Mustansiriyah Journal for Pharmaceutical Sciences is the property of Republic of Iraq Ministry of Higher Education & Scientific Research (MOHESR) and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

In the present research, the design and synthesis of polyfunctionalized pyrrole derivatives using one-pot, multi-component reactions including aromatic aldehydes, ethyl acetoacetate, thiadiazole derivatives, and nitromethane in the presence of 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate ([Simp]HSO4]) ionic liquid and under solvent-free conditions were discussed. Since pyrrole derivatives have various medicinal properties such as antibacterial, antiviral, anti-inflammatory, and antioxidant activity, and they are very important from biological and medicinal points of view, therefore, it is very important to provide efficient and green methods for preparing these compounds.On the other hand, considering the environmental pollution and the development of the green chemistry approach, and the recommendation to reduce the use of toxic solvents in chemical reactions, extensive research to find new synthetic methods based on the use of environmentally friendly solvents and catalysts that lead to the reduction of waste materials and products. This method used the ionic liquid 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate ([Simp]HSO4]) as a recoverable catalyst in the green synthesis of pyrrole derivatives.This method has some advantages such as high yield, no use of organic solvents, mild reaction conditions, short reaction time, and easy separation without using chromatography. The structure of all products was characterized using physical data as well as 1HNMR, 13CNMR and IR spectrum.

We designed and synthesized two novel blue pyrrole derivatives, 2-(3-cyano-4-(4-(dibutylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (BAPCP) and 2-(3-cyano-4-(4-(dihexylamino)phenyl)-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)malononitrile (HAPCP), as potential candidates for use in image sensor color filters. The properties of these new compounds were evaluated, focusing on their optical and thermal characteristics in solution and color filter film forms. The molar extinction coefficient values of BAPCP and HAPCP in solution were 6.03 × 104 and 6.91 × 104 L/mol·cm. The molar extinction coefficient of HAPCP was 4.5 times higher than that of the commercially used Disperse Blue 359. The synthesized compounds exhibited transmittance values that meet commercial requirements, with 88.6% at 450 nm and 0.73% at 530 nm. Both newly synthesized compounds met the decomposition temperature requirement of over 230 °C, which is necessary for the manufacturing process of image sensor color filters. The decomposition temperatures of both compounds were approximately 19 °C higher than that of Disperse Blue 359. When the thermal stability of color filter films for image sensors was evaluated, BAPCP demonstrated excellent optical properties before and after thermal stability testing, maintaining its characteristics in an optimized molecular form. Accordingly, BAPCP appears to have favorable potential as a blue colorant for image sensors, attributed to its superior optical and thermal stability characteristics.

The document is a contents list for the journal "Chemical Communications" published in 2024. It includes a variety of articles on topics such as cell-free synthetic biology, metal-organic framework-based materials for cancer therapy, and the formation of iminium ions in metal halide perovskites. The journal is published by The Royal Society of Chemistry, a leading chemistry community. The document provides a glimpse into the research and discoveries in the field of chemistry. [Extracted from the article]

Presented herein is the synthesis of diversely functionalized pyrrolizines from the reaction of N-alkoxycarbamoyl pyrroles with CF3-ynones. The formation of the product is based on a C–H bond activation-initiated cascade process including N-alkoxycarbamoyl group-directed alkenylation of the pyrrole scaffold followed by simultaneous intramolecular nucleophilic addition along with cleavage and transfer of the directing group. By taking advantage of the rich chemistry of the transferred alkoxycarbamoyl moiety, the products could be transformed into a series of structurally and biologically interesting pyrrolizine derivatives. To our knowledge, this is the first example in which the N-alkoxycarbamoyl unit acted as a transferable and transformable directing group for the divergent synthesis of pyrrolizines. [ABSTRACT FROM AUTHOR]

3,4-Fused pyrrolocoumarins, synthetically prepared or naturally occurring, possess interesting biological properties. In this review, the synthetic strategies for the synthesis of the title compounds are presented along with their biological activities. Two routes are followed for that synthesis. In one, the pyrrole ring is formed from coumarin derivatives, such as aminocoumarins or other coumarins. In the other approach, the pyranone moiety is built from an existing pyrrole derivative or through the simultaneous formation of coumarin and pyrrole frameworks. The above syntheses are achieved via 1,3-dipolar cycloaddition reactions, Michael reaction, aza-Claisen rearrangement reactions, multi-component reactions (MCR), as well as metal-catalyzed reactions. Pyrrolocoumarins present cytotoxic, antifungal, antibacterial, α-glucosidase inhibition, antioxidant, lipoxygenase (LOX) inhibition, and fluorescent activities, as well as benzodiazepine receptor ability. [ABSTRACT FROM AUTHOR]

The synthesis of a new tetracationic porphyrin derivative is described. Contrary to the best known derivatives in the literature, which are derived from 5,10,15,20-tetrakis-4-pyridylporphyrin (TPyP), in this procedure we start from 5,10,15,20-tetrakis-(4-carboxymethoxyphenyl)porphyrin (TPPCOOMe), obtained by the condensation reaction between pyrrole and 4-formylbenzoate. The reaction is carried out in refluxed xylene, avoiding the use of halogenated solvents. The final product, 5,10,15,20-tetrakis-(4-(3-carbamoyl-pyridyl)-methylphenyl)porphyrin bromide (P15p), exhibits four cationic portions that make it soluble in water and suitable for G4 stabilization. The choice to synthesize a derivative of TPPCOOMe is based on the idea of having a possible stabilizer that, unlike those obtained from TPyP, shows the cationic moieties farther from the porphyrin core and thus closer to the phosphate groups present on the G4 loops. [ABSTRACT FROM AUTHOR]

Pyrrole‐2,5‐dicarboxylic acid (PDCA) is a heterocyclic aromatic dicarboxylic acid that may emerge as a new monomer for polyester production. Compared to its structurally related and bio‐based furan‐2,5‐dicarboxylic acid (FDCA) that is already used for the production of polyethylene furanoate (PEF), PDCA shows excellent potential as its nitrogen can be targeted for further derivatization, thus enabling tuning of the properties of a PDCA containing polymer. In light of this, we recognized the need to explore efficient synthetic approaches for producing PDCAs in high yields. Here, we report a five‐step synthesis route for N‐substituted PDCAs starting from pyrrole, with total yields up to 42 %. The synthetic approach allowed the introduction of several different functional moieties to the pyrrole nitrogen, such as aliphatic saturated and unsaturated side‐chains, as well as benzylic groups. [ABSTRACT FROM AUTHOR]

It is still believed that the progress of Green Chemistry necessities to upsurge at a higher pace, if 'molecular science' is to meet the encounters of sustainability. And it is also aforesaid that the revolution of a particular day becomes the new-fangled belief of the next. Therefore, keeping the importance of sustainability as well as green chemistry in mind, herein we report a green perspective of a very well-known named reaction, dubbed as Paal–Knorr pyrrole synthesis. In this document, we have tried to cover some interesting synthetic green approaches belonging to this particular class. We hope that this review article will be very useful to the researchers working in organic chemistry in general and heterocyclic chemistry in particular. [ABSTRACT FROM AUTHOR]

A convenient Cu(I) Catalyzed three‐component coupling strategy for the synthesis of polysubstituted pyrroles is developed using simple and readily available building blocks like, 1, 3‐dicarbonyl compound, aryl amine, and β‐nitrostyrene. CuI has been rarely explored for the pyrrole ring synthesis and a comparative analysis of our current catalyst with a range of previously reported catalysts suggested that, CuI is one of the best catalysts for the multicomponent synthesis of polysubstituted pyrrole derivatives. Notably, this process has several advantages, including a simple and practical set‐up with hassle free reaction conditions, extensive substrate scope, short reaction time, high atom economy and environmentally favorable approach. This methodology provides an alternative approach to the highly substituted pyrroles and under optimized reaction conditions, polysubstituted pyrroles were formed in good to excellent yields. Cu(I) catalyzed Mannich reactions followed by Michael addition reactions along with subsequent intramolecular cyclization are believed to be the key steps of this reaction process. [ABSTRACT FROM AUTHOR]

Substituted pyrroles were obtained as a result of metal‐catalyzed cyclization of α propargyl acetophenone and α‐propargyl‐β‐ketoesters with semicarbazide. Optimum conditions and general procedures with high yields were established in a single pot. Eleven different N‐ureido‐pyrrole derivatives were successfully yielded. Different ynone derivatives having various functionalities did not affect the cyclization reaction but except a slight decrease in product yield. Screening of optimum catalyst revealed that gold(III) chloride was the best catalyst for the cyclization reaction. We believe that this is the first time an N‐ureido‐pyrrole skeleton starting from ynone has been synthesized in the literature. [ABSTRACT FROM AUTHOR]

2‐Nitroglycals are important synthons for biological active 2‐aminoglycosides, glycoconjugates and natural products synthesis. Herein, we summarized the recent advances of 2‐nitroglycals including its synthetic methods and its applications. Using 2‐nitroglycals, 2‐aminoglycosides, nitro‐polyol derivatives, sugar‐furan derivatives, sugar‐pyrrole molecules, 2,3‐diaminoglycosides and 2‐amino‐1,3‐dithioglycosides were obtained via Michael–type addition, retro‐Henry‐type reaction, C1/C3‐Ferrier rearrangement and [3+2] N‐heterocyclic addition. Most of these conversions are achieved via mild organo‐catalysis glycosylation methods. [ABSTRACT FROM AUTHOR]

Synthesis of heteroaryl ortho‐substituted anilines is hitherto challenging. Herein we report scope and limitation of method for annulation of 1‐(2‐nitroaryl)pyrroles and derivatives of 2‐aminobenzyl alcohol to afford ortho‐substituted pyrrolo[1,2‐a]quinoxalin‐4‐yl anilines. Reaction conditions contained elemental sulfur as promoter, while were tolerant of a wide range of aryl and heteroaryl amines. Our method would offer a feasible tactic to yield anilines steric bulk with ortho heterocyclic substituents. [ABSTRACT FROM AUTHOR]

Heterocyclic compounds such as pyrrole and pyrrolidine derivatives have a broad spectrum of biological activity, being widely used as pharmacophore to design novel bioactive compounds. In this work, sixteen pyrrole and pyrrolidine derivatives were synthesized and evaluated for their growth inhibitory activity on two human cancer cells lines: breast cancer MDA‐MB‐231 and chronic myelogenous leukemia (K562). Eight compounds showed activity against at least one tumor cell line (IC50=49.15–195.9 μM). The compounds were tested in non‐cancerous human lung fibroblasts WI‐26VA4 to evaluate their selectivity index. In addition, Hierarchical Cluster Analysis (HCA) studies were carried out in attempt to establish a structure‐activity relationship. [ABSTRACT FROM AUTHOR]

Benzimidazole-based pyrrole/piperidine analogs (1–26) were synthesized and then screened for their acetylcholinesterase and butyrylcholinesterase activities. All the analogs showed good to moderate cholinesterase activities. Synthesized compounds (1–13) were screened in cholinesterase enzyme inhibition assays and showed AChE activities in the range of IC50 = 19.44 ± 0.60 µM to 36.05 ± 0.4 µM against allanzanthane (IC50 = 16.11 ± 0.33 µM) and galantamine (IC50 = 19.34 ± 0.62 µM) and varied BuChE inhibitory activities, with IC50 values in the range of 21.57 ± 0.61 µM to 39.55 ± 0.03 µM as compared with standard allanzanthane (IC50 = 18.14 ± 0.05 µM) and galantamine (IC50 = 21.45 ± 0.21 µM). Similarly, synthesized compounds (14–26) were also subjected to tests to determine their in vitro AChE inhibitory activities, and the results obtained corroborated that all the compounds showed varied activities in the range of IC50 = 22.07 ± 0.13 to 42.01 ± 0.02 µM as compared to allanzanthane (IC50 = 20.01 ± 0.12 µM) and galantamine (IC50 = 18.05 ± 0.31 µM) and varied BuChE inhibitory activities, with IC50 values in the range of 26.32 ± 0.13 to 47.03 ± 0.15 µM as compared to standard allanzanthane (IC50 = 18.14 ± 0.05 µM) and galantamine (IC50 = 21.45 ± 0.21 µM). Binding interactions of the most potent analogs were confirmed through molecular docking studies. The active analogs 2, 4, 10 and 13 established numerous interactions with the active sites of targeted enzymes, with docking scores of −10.50, −9.3, −7.73 and −7.8 for AChE and −8.97, −8.2, −8.20 and −7.6 for BuChE, respectively. [ABSTRACT FROM AUTHOR]

In this research new derivatives of pyrroles in good yields were prepared using multicomponent reactions of amoxicillin, activated acetylenic compounds, and alkyl bromides in water as solvent at room temperature in the presence of catalytic amounts of active carbon. The short time of reaction, high yields of product, and easy separation of them are some advantages of this procedure. In this research, the adsorption process was investigated for cefixime and amoxicillin as antibiotic drugs removal using active carbon and zeolite as organic and natural adsorbents in continuous and batch reactors in lab-scale, and the experiments were continued continuously using an adsorbent that absorbed more the two drugs. According to obtained results, the active carbon adsorbed both cefixime and amoxicillin but the zeolite did not adsorb the amoxicillin but adsorbed the high percentage of cefixime in the batch procedure. It can be concluded that some advantages of the continuous process compared to batch reactor are high performance of adsorbent, short time of process, and high percentage of adsorption. Green chemistry is the use of a set of principles to reduce or eliminate the use or generation of unsafe materials in the design, fabrication, and applications of chemical products. Among solvents, water is a green solvent and very suitable for performing organic reaction. The present procedure avoids the use of toxic solvents. According to obtained results, the active carbon adsorbed both cefixime and amoxicillin, but the zeolite did not adsorb the amoxicillin but adsorbed the high percentage of cefixime in the batch procedure. [ABSTRACT FROM AUTHOR]

In the present research, the design and synthesis of polyfunctionalized pyrrole derivatives using one-pot, multi-component reactions including aromatic aldehydes, ethyl acetoacetate, thiadiazole derivatives, and nitromethane in the presence of 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate ([Simp]HSO4]) ionic liquid and under solvent-free conditions were discussed. Since pyrrole derivatives have various medicinal properties such as antibacterial, antiviral, anti-inflammatory, and antioxidant activity, and they are very important from biological and medicinal points of view, therefore, it is very important to provide efficient and green methods for preparing these compounds.On the other hand, considering the environmental pollution and the development of the green chemistry approach, and the recommendation to reduce the use of toxic solvents in chemical reactions, extensive research to find new synthetic methods based on the use of environmentally friendly solvents and catalysts that lead to the reduction of waste materials and products. This method used the ionic liquid 3-sulfonic acid 1-imidazolopyridinium hydrogen sulfate ([Simp]HSO4]) as a recoverable catalyst in the green synthesis of pyrrole derivatives.This method has some advantages such as high yield, no use of organic solvents, mild reaction conditions, short reaction time, and easy separation without using chromatography. The structure of all products was characterized using physical data as well as ¹HNMR, 13CNMR and IR spectrum. [ABSTRACT FROM AUTHOR]

Molecular docking simulation and synthesis of five compounds of N2, N4-bis (2-(4-substituted phenyl)-4-oxothiazolidin-3-yl)-3,5-dimethyl-1H-pyrrole-2,4-dicarboxamide was carried out to evaluate their theoretical binding affinities, targeting acute myeloid leukemia (AML). The chemical structure of the molecules was accurately drawn using ChemDraw Professional 19.1 software. The designed compounds were evaluated for their selectivity towards FLT3's ATP pocket (PDB ID:6JQR) in comparison with the reference ligand (Gilteritinib) by using GOLD suite from the Cambridge Crystallographic Data Centre (CCDC) software (Version 2021.2.0). All the designed compounds exhibited good binding energies with the receptor active pocket and had promising activity. Compounds 2E and 3E showed the highest PLP Fitness (83.30, 80.86 respectively) and it is higher than that of Gilteritinib (71.91). In-silico ADME and drug-likeness studies were performed by using the Swiss ADME server. The results showed that most of the designed compounds expected to be absorbed from the GIT. Compounds 2B-E have high expected GI absorption. All the investigated compounds have no predicted BBB penetration. Additionally, compounds 2A, 2C, 2D, and 3A are not a substrate to P-gps which may indicate a lower expected incidence of resistance by cancer cells in vitro studies. Finally, all of the investigated compounds are not considered to inhibit CYP1A2 enzyme, except for compounds 2A and 3D.

In this study, Co3O4 nanoparticles were used as nanocatalyst for two different series of nitrogen-containing heterocyclic compounds, including pyrrole (Pyo) derivatives and pyrano [2, 3-c]pyrazole (Pya[2, 3-c]Pyz) derivatives. In the synthesis of derivatives, using 15 mol% and 10 mol% of the catalyst for Pyo derivatives and Pya[2, 3-c]Pyz derivatives, respectively, an efficiency between 83% and 96%, were observed. In addition, novel derivatives of Pyo and Pya[2,3-c]Pyz were synthesized and their structures were confirmed. In general, the advantages of using cobalt nanoparticles compared to previous reports include the synthesis of new derivatives, lower temperature used in the synthesis of derivatives, shorter synthesis time and high efficiency. The biological properties of the synthesized products, such as antibacterial, antifungal, and antioxidant properties, were tested and investigated. In antibacterial and antifungal tests, IZD, MIC, MBC, and MFC were measured and reported. In antioxidant activity, IC50 was calculated and reported. High reusability, green and environmentally friendly, synthesis of new derivatives and synthesis of products with higher efficiency and shorter time were the important benefits of using cobalt nanoparticles as a catalyst. In antioxidant tests, the IC50 for synthesized Pyo derivatives and Pya[2, 3-c] Pyz derivatives were between 12.2 and 13.71 μg/mL, and 16.18–17.75 μg/mL, respectively. In antimicrobial testes, the MIC for synthesized Pyo derivatives and Pya[2, 3-c]Pyz derivatives were between 2 and 4,096 μg/mL, and 2–2048 μg/mL, respectively. The results showed that the antioxidant property of Pyo derivatives were more than Pya[2, 3-c] Pyz derivatives, but the antimicrobial effect of Pya[2,3-c] Pyz derivatives were more than Pyo derivatives. The antioxidant results proved that the activity of Pyo derivatives and Pya[2, 3-c] Pyz derivatives does not depend on the substitutions of the derivatives and is close to each other. Therefore, based on this, a proposed mechanism for stability of DPPH by Pyo derivatives and Pya[2, 3-c] Pyz derivatives were suggested. Finally, based on the more stable resonance structures of Pyo derivatives, compared to Pya[2, 3-c] Pyz derivatives, its high antioxidant property was justified. Pya[2, 3-c] Pyz derivatives has two heterocyclic rings connected together pyrano and pyrazole, but Pyo derivatives has only one heterocyclic ring (pyrrole). So high antimicrobial property of Pya[2, 3-c] Pyz derivatives compared to Pyo derivatives can be attributed to having two bioactive heterocyclic rings.

A palladium‐catalyzed norbornene‐mediated regioselective direct C−H glycosylation of free N−H pyrrole and electron‐deficient pyrrole derivatives has been developed. The reaction involves the use of a PdII catalyst and norbornene as a transpositional co‐catalyst, in which a pyrrole‐ and norbornyl‐fused palladaheterocycle forms as the key intermediate. The 2‐substituted pyrroles, and other 2,3‐disubstituted pyrroles underwent the selective C5 glycosylation. This reaction is compatible with various types of glycosyl chlorides including D‐mannose, L‐rhamnose, D‐mannofuranose, and D‐ribofuranose. The viability of this strategy is showed by gram‐scale, various synthetic transformation and functionalization. [ABSTRACT FROM AUTHOR]

In this study, two Bodipy compounds were synthesized using 2,4-dimethyl pyrrole as a pyrrole derivative. It was desired that both intermediates and target compounds can be obtained purely from these synthesized products, and for this reason, column chromatography was applied at every stage of the synthesis. The products were synthesized by hand and characterized by various methods. First, melting point determination and FT-IR spectra were examined, then, after the analysis of the functional group with FT-IR spectroscopy,1H and 13C-NMR spectra of these compounds were taken. While taking the NMR spectra, deuteuro-chloroform was used as the solvent. These synthesized compounds were shortly named as B1 and B2. After the initial characterization processes, some optical properties of the compounds were examined with UV–vis spectroscopy and fluorescence spectroscopy. In addition, the effect of solvent on the fluorescence properties of these compounds was investigated. [ABSTRACT FROM AUTHOR]

Herein, a palladium-catalyzed and ligand-controlled protocol for the divergent synthesis of pyrrole[2,3-b]indole and urea derivatives has been described. Pyrrole[2,3-b]indoles ("cyclization on" products) via tandem cyclization of o-alkynylanilines with isocyanides in the absence of a ligand and ureas ("cyclization off" products) via oxidative amination of anilines with isocyanides in the presence of a ligand were obtained both in moderate to good yields with high selectivity. In this chemistry, cyclic and acyclic products were easily accessed with the same starting materials under the regulation of the ligand. [ABSTRACT FROM AUTHOR]