Journal articles: 'Imidazol'

1

Ganguly, Swastika, Vatsal Vithlani, Anup Kesharwani, et al. "Synthesis, antibacterial and potential anti-HIV activity of some novel imidazole analogs." Acta Pharmaceutica 61, no. 2 (2011): 187–201. http://dx.doi.org/10.2478/v10007-011-0018-2.

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Synthesis, antibacterial and potential anti-HIV activity of some novel imidazole analogs A series of 1-(2-methyl-4-nitro-imidazol-1-yl)-3-arylaminopropan-2-ones (2a-e), 2-methyl-5-nitro-1-{2-[arylmethoxy] ethyl}-1H-imidazoles (5a-d), and N-(3-hydroxyphenyl)-2-(substituted imidazol-1-yl)alkanamides (8a-e) were synthesized with the aim to develop novel imidazole analogs with broad-spectrum chemotherapeutic properties. Title compounds were evaluated for their anti-HIV and antibacterial activities.

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Zhou, Qifan, Fangyu Du, Yajie Shi, Ting Fang, and Guoliang Chen. "Synthesis and Analysis of 1-Methyl-4-Phenyl-1H-Imidazol-2-Amine." Journal of Chemical Research 42, no. 12 (2018): 608–10. http://dx.doi.org/10.3184/174751918x15414286606248.

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A practical synthetic route to an important pharmaceutical intermediate 1-methyl-4-phenyl-1H-imidazol-2-amine, via a three-step sequence involving cyclisation, hydrolysis and methylation, is reported. In the process of optimisation, a novel chemical entity was isolated and confirmed to be 2,6-diphenyl-1H-imidazo[1,2-a]imidazole by MS, 1H NMR and 13C NMR. The scale-up experiment was carried out to provide 1-methyl-4-phenyl-1H-imidazol-2-amine in 27.4% total yield.

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3

Lipson, Victoria V., Tetiana L. Pavlovska, Nataliya V. Svetlichnaya, et al. "Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds." Beilstein Journal of Organic Chemistry 15 (May 6, 2019): 1032–45. http://dx.doi.org/10.3762/bjoc.15.101.

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The unexpectedly uncatalyzed reaction between 2-amino-4-arylimidazoles, aromatic aldehydes and Meldrum’s acid has selectively led to the corresponding Knoevenagel–Michael adducts containing a free amino group in the imidazole fragment. The adducts derived from Meldrum’s acid have been smoothly converted into 1,7-diaryl-3-amino-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-ones and 3-(2-amino-4-aryl-1H-imidazol-5-yl)-3-arylpropanoic acids. The interaction of 2-amino-4-arylimidazoles with aromatic aldehydes or isatins and acyclic methylene active compounds has led to the formation of pyrrolo[1,2-c]imidazole-6-carbonitriles, pyrrolo[1,2-с]imidazole-6-carboxylates and spiro[indoline-3,7'-pyrrolo[1,2-c]imidazoles], which can be considered as the analogues of both 3,3’-spirooxindole and 2-aminoimidazole marine sponge alkaloids.

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4

Balewski, Łukasz, Franciszek Sączewski, Patrick J. Bednarski, et al. "Synthesis, Structure and Cytotoxicity Testing of Novel 7-(4,5-Dihydro-1H-imidazol-2-yl)-2-aryl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-Imine Derivatives." Molecules 25, no. 24 (2020): 5924. http://dx.doi.org/10.3390/molecules25245924.

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The appropriate 1-arylhydrazinecarbonitriles 1a–c are subjected to the reaction with 2-chloro-4,5-dihydro-1H-imidazole (2), yielding 7-(4,5-dihydro-1H-imidazol-2-yl)-2-aryl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-imines 3a–c, which are subsequently converted into the corresponding amides 4a–e, 8a–c, sulfonamides 5a–n, 9, ureas 6a–I, and thioureas 7a–d. The structures of the newly prepared derivatives 3a–c, 4a–e, 5a–n, 6a–i, 7a–d, 8a–c, and 9 are confirmed by IR, NMR spectroscopic data, as well as single-crystal X-ray analyses of 5e and 8c. The in vitro cytotoxic potency of these compounds is determined on a panel of human cancer cell lines, and the relationships between structure and antitumor activity are discussed. The most active 4-chloro-N-(2-(4-chlorophenyl)-7-(4,5-dihydro-1H-imidazol-2-yl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)benzamide (4e) and N-(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)-[1,1′-biphenyl]-4-sulfonamide (5l) inhibits the growth of the cervical cancer SISO and bladder cancer RT-112 cell lines with IC50 values in the range of 2.38–3.77 μM. Moreover, N-(7-(4,5-dihydro-1H-imidazol-2-yl)-2-phenyl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)-4-phenoxybenzenesulfonamide (5m) has the best selectivity towards the SISO cell line and induces apoptosis in this cell line.

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5

Arduengo, Anthony J., Jens R. Goerlicha, Fredric Davidson, and William J. Marshall. "Carbene Adducts of Dimethylcadmium." Zeitschrift für Naturforschung B 54, no. 11 (1999): 1350–56. http://dx.doi.org/10.1515/znb-1999-1102.

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The first examples of carbene-cadmium complexes are reported from the reactions of a variety of imidazol-2-ylidenes or imidazolin-2-ylidenes with dimethylcadmium. Four new carbene complexes are characterized by NMR spectroscopy (1H , 13C and 113Cd). The cadmium centers are strongly shifted downfield (100 -150 ppm) by interaction with the carbenes. X-ray structures are reported for three carbene-cadmium 1:1 adducts. The cadmium centers exhibit distorted trigonal-planar geometries in which the carbene ligands have an average 18.2 pm longer bond distance to cadmium compared to the methyl groups. The planes of cadmium coordination are twisted with respect to the plane of the imidazole ring. The more basic imidazolin-2-ylidene is shown to displace imidazol-2-ylidenes from the cadmium center.

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6

Demchenko, Sergii, Roman Lesyk, Oleh Yadlovskyi, et al. "Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts." Molecules 26, no. 14 (2021): 4253. http://dx.doi.org/10.3390/molecules26144253.

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A series of novel 3-aryl-5H-pyrrolo[1,2-a]imidazole and 5H-imidazo[1,2-a]azepine quaternary salts were synthesized in 58–85% yields via the reaction of 3-aryl-6, 7-dihydro-5H-pyrrolo[1,2-a]imidazoles or 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines and various alkylating reagents. All compounds were characterized by 1H NMR, 13C NMR, and LC-MS. The conducted screening studies of the in vitro antimicrobial activity of the new quaternary salts derivatives established that 15 of the 18 newly synthesized compounds show antibacterial and antifungal activity. Synthesized 3-(3,4-dichlorohenyl)-1-[(4-phenoxyphenylcarbamoyl)-methyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-1-ium chloride 6c possessed a broad activity spectrum towards Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Cryptococcus neoformans, with a high hemolytic activity against human red blood cells and cytotoxicity against HEK-293. However, compound 6c is characterized by a low in vivo toxicity in mice (LD50 > 2000 mg/kg).

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7

Parmar, Tejasvi H., Chetan B. Sangani, and Mahesh Kulkarni. "Synthesis of novel drug-like small molecules library based on 1." Australian Journal of Chemistry 75, no. 4 (2022): 276–84. http://dx.doi.org/10.1071/ch21238.

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A series of novel ‘drug-like’ small molecules based on 1H-benzo[d]imidazole derivatives bearing furan-2-yl, 4-piperidine and 5-aryl/aminoaryl substitutions were designed and synthesised. The key intermediate tert-butyl-4-(5-bromo-2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (5) was synthesised via sequential reaction starting from 4-bromo-1-fluoro-2-nitrobenzene (1). The 5-aryl-substituted molecular library was generated via Suzuki–Miyura coupling of tert-butyl-4-(5-bromo-2-(furan-2-yl)-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (5) with various boronic acids while Buchwald coupling of 5 with various anilines generated the second molecular library of tert-butyl-4-(2-(furan-2-yl)-5-(arylamino)-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylates. The structures of all the newly synthesised compounds were confirmed by spectral analysis. The optimised procedure gives easy access to two new molecular libraries of 1H-benzo[d]imidazoles with operational simplicity and good yield.

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8

Bhat, Mashooq Ahmad, Mohamed A. Al-Omar, Ahmed M. Naglah, Atef Kalmouch, and Abdullah Al-Dhfyan. "Synthesis and Characterization of Novel Biginelli Dihydropyrimidinone Derivatives Containing Imidazole Moiety." Journal of Chemistry 2019 (May 13, 2019): 1–7. http://dx.doi.org/10.1155/2019/3131879.

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Enaminone, (2E)-1-[4-(1H-imidazol-1-yl) phenyl]-4-methylpent-2-en-1-one (II) was synthesized by refluxing 1-[4-(1H-imidazol-1-yl) phenyl] ethan-1-one (I) with dimethylforamide dimethylacetal (DMF–DMA) under solvent-free condition for 12 hours. Finally, the dihydropyrimidinone derivatives containing imidazole moiety (1–15) were obtained by reacting enaminone, (2E)-1-[4-(1H-imidazol-1-yl) phenyl]-4-methylpent-2-en-1-one (II) with urea and different substituted benzaldehydes in the presence of glacial acetic acid. Dihydropyrimidinone derivatives containing imidazole moiety were synthesized in excellent yield by means of a simple and efficient method. All the compounds were confirmed by elemental analysis. The structures of all the compounds were confirmed by modern spectroscopic methods.

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9

Grieco, Gabriele, Olivier Blacque, and Heinz Berke. "A facile synthetic route to benzimidazolium salts bearing bulky aromatic N-substituents." Beilstein Journal of Organic Chemistry 11 (September 17, 2015): 1656–66. http://dx.doi.org/10.3762/bjoc.11.182.

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An atom-economic synthetic route to benzimidazolium salts is presented. The annulated polycyclic systems: 1,3-bis(2,4,6-trimethylphenyl)-1H-benzo[d]imidazol-3-ium chloride (1-Cl), 1,3-bis(2,6-diisopropylphenyl)-1H-benzo[d]imidazol-3-ium chloride (2-Cl), 1,3-diphenyl-1H-benzo[d]imidazol-3-ium chloride (3-Cl), and 1,3-di(pyridin-2-yl)-1H-benzo[d]imidazol-3-ium chloride (4-Cl) were prepared in a two-step synthesis avoiding chromatographic work-up. In the key step triethyl orthoformate is reacted with the correspondingN1,N2-diarylbenzene-1,2-diamines and then further transformed in situ, by alkoxy abstraction using trimethylsilyl chloride (TMSCl), and concomitant imidazole ring closure.

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10

Pranabes, Bhattacharyya, Medda Arunima, Samanta Anuva, Guchhait Nikhil, and R. Das Asish. "Silica gel-mediated microwave-assisted efficient synthesis of highly substituted imidazoles and exploration of naked eye/colorimetric sensor for anions." Journal of Indian Chemical Society Vol. 88, Jul 2011 (2011): 983–93. https://doi.org/10.5281/zenodo.5785102.

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Department of Chemistry, University of Calcutta, Kolkata-700 009, India E-mail: ardchem@caluniv.ac.in, ardas66@rediffmail.com Manuscript received 09 November 2010, revised 29 December 2010, accepted 30 December 2010 Ammonium formate and silica gel have been found to be efficient reagent combination for an improved and very rapid one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in excellent yields. Multicomponent condensation in the presence of solid support with operational simplicity, inexpensive reagents, high yield or products, tolerance of sensitive functionalities, use of non-hazardous and non-toxic reagents combination under solvent-less condition makes this synthetic protocol, an attractive one. Moreover, trisubstituted Imidazole, 2-(4,5-diphenyl-1H imidazol-2-yl)-4-phenylazo-phenol or tetrasubstituted imidazole, 2-(4,5-diphenyl-l-thiazol-2-yl)-lH-imidazol-2-yl)-4-phenylazophenol have been found to be naked eye and colorimetric sensor for anions like F-, Cl-, CH3COO-, H2PO4- offering very high binding constant with F- ion (K = 1.39 x 104 M-1).

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11

Mlostoń, Grzegorz, Małgorzata Celeda, Katarzyna Urbaniak, et al. "Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium salts." Beilstein Journal of Organic Chemistry 15 (February 19, 2019): 497–505. http://dx.doi.org/10.3762/bjoc.15.43.

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Adamantyloxyamine reacts with formaldehyde to give N-(adamantyloxy)formaldimine as a room-temperature-stable compound that exists in solution in monomeric form. This product was used for reactions with α-hydroxyiminoketones leading to a new class of 2-unsubstituted imidazole 3-oxides bearing the adamantyloxy substituent at N(1). Their reactions with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or with acetic acid anhydride occurred analogously to those of 1-alkylimidazole 3-oxides to give imidazol-2-thiones and imidazol-2-ones, respectively. Treatment of 1-(adamantyloxy)imidazole 3-oxides with Raney-Ni afforded the corresponding imidazole derivatives without cleavage of the N(1)–O bond. Finally, the O-alkylation reactions of the new imidazole N-oxides with 1-bromopentane or 1-bromododecane open access to diversely substituted, non-symmetric 1,3-dialkoxyimidazolium salts. Adamantyloxyamine reacts with glyoxal and formaldehyde in the presence of hydrobromic acid yielding symmetric 1,3-di(adamantyloxy)-1H-imidazolium bromide in good yield. Deprotonation of the latter with triethylamine in the presence of elemental sulfur allows the in situ generation of the corresponding imidazol-2-ylidene, which traps elemental sulfur yielding a 1,3-dihydro-2H-imidazole-2-thione as the final product.

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Martens, Sean J., and David K. Geiger. "Structural characterization of two tetrachloridozincate salts of 4-carboxy-1H-imidazol-3-ium: a salt hydrate and a co-crystal salt hydrate." Acta Crystallographica Section E Crystallographic Communications 73, no. 2 (2017): 162–67. http://dx.doi.org/10.1107/s2056989017000317.

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Imidazole-containing compounds exhibit a myriad of pharmacological activities. Two tetrachloridozincate salts of 4-carboxy-1H-imidazol-3-ium, ImHCO2H+, are reported. Bis(4-carboxy-1H-imidazol-3-ium) tetrachloridozincate monohydrate, (C4H5N2O2)2[ZnCl4]·H2O, (I), crystallizes as a monohydrate salt, while bis(4-carboxy-1H-imidazol-3-ium) tetrachloridozincate bis(1H-imidazol-3-ium-4-carboxylato) monohydrate, (C4H5N2O2)2[ZnCl4]·2C4H4N2O2·H2O, (II), is a co-crystal salt with six residues: two ImHCO2H+cations, two formula units of the zwitterionic 1H-imidazol-3-ium-4-carboxylate, ImHCO2, one tetrachloridozincate anion and one water molecule disordered over two sites in a 0.60 (4):0.40 (4) ratio. The geometric parameters of the ImHCO2H+and the ImHCO2moieties are the same within the standard uncertainties of the measurements. Both compounds exhibit extensive hydrogen bonding, including involvement of the tetrachloridozincate anion, resulting in interconnected chains of anions joined by water molecules.

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13

Bhaskar, J. Udaya, G. Srinivasa Rao, Pranab Chatterjee, D. K. Sahoo, S. Srinivasa Rao, and B. Pulla Rao. "Synthesis, Characterization and Antibacterial Screening of Some Novel Compounds containing Multi N-Fused Heterocycles." Asian Journal of Chemistry 36, no. 9 (2024): 2185–90. http://dx.doi.org/10.14233/ajchem.2024.32265.

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An attempt has been made to synthesize novel multi N-fused heterocyclic compounds containing four divergent heterocyclic compounds such as imidazole, pyrimidine, morpholine and indole. A series of N-(4-(1H-benzo[d]imidazol-2-yl)-6-phenylpyrimidin-2-yl)-2-(4-((E)-3-(2-morpholino-9H-pyrido[2,3-b]indol-3-yl)acryloyl)phenylamino)acetamide (6a-c) was accomplished in good yields with 1-(1H-benzo-[d]imidazol-2-yl)ethanone (1) as starting compound and through the formation of (E)-1-(1H-benzo[d]imidazol-2-yl)-3-phenylprop-2-ne-1-ones (2a-c), 4-(1H-benzo[d]imidazol-2-yl)-6-phenylpyrimidin-2-amines (3a-c) and N-(4-(1H-benzo[d]imidazol-2-yl)-6-phenylpyrimidin-2-yl)-2-chloroacetamides (4a-c) as intermediates on extension of the reaction. The structural elucidation of all the synthesized compounds were characterized by IR, 1H NMR, mass spectral data and elemental analysis. Further, the title compounds were also used to evaluate their antibacterial activity.

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Li, Steven A., Rebecca J. Zheng, Kenneth Sue, et al. "Discovery and Preliminary Structure-Activity Investigation of 3-Substituted-1H-imidazol-5-yl-1H-indoles with In Vitro Activity towards Methicillin-Resistant Staphylococcus aureus." Antibiotics 11, no. 10 (2022): 1450. http://dx.doi.org/10.3390/antibiotics11101450.

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Antibiotics have been the cornerstone of modern medicine saving lives by virtue of being able to cure infectious diseases and to prevent infections in those who are immune compromised. Their intense use has led to a surging increase in the incidence of antibiotic-resistant bacteria resulting in a desperate need for antibiotics with new mechanisms of action. As part of our search for new antimicrobials we have screened an in-house library of compounds and identified two 3-substituted-1H-imidazol-5-yl-1H-indoles as weak growth inhibitors (MIC 16 µg/mL) against methicillin-resistant Staphylococcus aureus (MRSA). An extensive library of analogues was prepared using the Van Leusen three-component reaction, biological evaluation of which led to the identification of two analogues (26 and 32) with favorable anti-MRSA activity (MIC ≤ 0.25 µg/mL) which also lacked cytotoxic or hemolytic properties. The screening campaign also identified two derivatives, a phenethyl-indole-imidazole 57 and a 5-phenyl-1H-imidazole 111 that were non-toxic selective antifungals towards Cryptococcus neoformans. These results have identified 3-substituted-1H-imidazol-5-yl-1H-indoles and 5-phenyl-1H-imidazoles as new structural scaffolds for further investigation as anti-MRSA and anti-C. neoformans agents, respectively.

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15

Ovonramwen, Oluwaseyi B., Bodunde J. Owolabi, and Abiodun Falodun. "Synthesis and Antimicrobial Activities of 1-((5-Chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide." Tanzania Journal of Science 47, no. 3 (2021): 1296–302. http://dx.doi.org/10.4314/tjs.v47i3.36.

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A new 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide was synthesized from methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate and ethylamine. The compound methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate was synthesized from methyl pyrrolidine-2-carboxylate and 5-chloro-4-chlorosulfonyl-1-ethyl-2-methyl-imidazole. The compounds were characterized based on FTIR, 1H, 13C NMR, and DEPT 135 analysis. Antimicrobial activities of the 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide against Gram-positive (methicillin-susceptible Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, and Bacillus subtilis), Gram-negative (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae), and Candida albicans were carried out using the standard microbiological method. The newly synthesized 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide had no activities against the tested organisms. Keywords: 1-((5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl)-N-ethylpyrrolidine-2-carboxamide; methyl-1-[(5-chloro-1-ethyl-2-methyl-1H-imidazol-4-yl)sulfonyl]pyrrolidine-2-carboxylate; L-proline; ethylamine.

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Aonofriesei, Florin. "Increased Absorption and Inhibitory Activity against Candida spp. of Imidazole Derivatives in Synergistic Association with a Surface Active Agent." Microorganisms 12, no. 1 (2023): 51. http://dx.doi.org/10.3390/microorganisms12010051.

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This paper’s purpose was to evaluate the interaction between three imidazole derivatives, (2-methyl-1H-imidazol-1-yl)methanol (SAM3), 1,1′-methanediylbis(1H-benzimidazole (AM5) and (1H-benzo[d]imidazol-1-yl)methanol 1-hydroxymethylbenzimidazole (SAM5) on the one hand, and sodium dodecyl sulphate (SDS) on the other, as antifungal combinations against Candida spp. Inhibitory activity was assessed using the agar diffusion method and Minimal Inhibitory Concentration (MIC) and showed moderate inhibitory activity of single imidazole derivatives against Candida spp. The mean value of MIC ranged from 200 µg/mL (SAM3) to 312.5 µg/mL (SAM3), while for SDS the MIC was around 1000 µg/mL. When used in combination with SDS, the imidazole derivatives demonstrated an improvement in their antifungal activity. Their MIC decreased over five times for AM5 and over seven times for SAM3 and SAM5, respectively, and ranged from 26.56 µg/mL (SAM3) to 53.90 µg/mL (AM5). Most combinations displayed an additive effect while a clear synergistic effect was recorded in only a few cases. Thus, the FIC Index (FICI) with values between 0.311 and 0.375 showed a synergistic effect against Candida spp. when SDS was associated with SAM3 (three strains), SAM5 (two strains) and AM5 (one strain). The association of imidazole derivatives with SDS led to the increased release of cellular material as well as the intracellular influx of crystal violet (CV), which indicated an alteration of the membrane permeability of Candida spp. cells. This favored the synergistic effect via increasing the intracellular influx of imidazoles.

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Balewski, Łukasz, and Anita Kornicka. "Synthesis of the Guanidine Derivative: N-{[(7-(4,5-Dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide." Molbank 2021, no. 3 (2021): M1246. http://dx.doi.org/10.3390/m1246.

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The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) with one measure of aniline in the presence of mercury(II) chloride and triethylamine in anhydrous dimethylformamide. The structure of product 3 was confirmed by 1H and 13C-NMR, infrared spectroscopy, and elemental analysis.

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Liu, Shenggui, Rongkai Pan, Wenyi Su, Guobi Li, and Chunlin Ni. "Synthesis of a Ruthenium Complex Based on 2,6-Bis[1-(Pyridin-2-yl)-1H-Benzo[d]Imidazol-2-yl]Pyridine and Catalytic Oxidation of (1H-Benzo[d]-Imidazol-2-yl)Methanol to 1H-Benzo[d]Imidazole-2-Carbaldehyde with H2O2." Journal of Chemical Research 41, no. 2 (2017): 88–92. http://dx.doi.org/10.3184/174751917x14858862342106.

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2,6-Bis[1-(pyridin-2-yl)-1H-benzo[d]-imidazol-2-yl]pyridine (bpbp), which has been synthesised by intramolecular thermocyclisation of N2,N6-bis[2-(pyridin-2-ylamino)phenyl]pyridine-2,6-dicarboxamide, reacts with sodium pyridine-2,6-dicarboxylate (pydic) and RuCl3 to give [Ru(bpbp)(pydic)] which can catalyse the oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehyde by H2O2. The optimal reaction conditions were: molar ratios of catalyst to substrate to H2O2 set at 1: 1000: 3000; reaction temperature 50 °C; reaction time 5 h. The yield of (1H-benzo[d]imidazol-2-yl) methanol was 70%.

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Hanson, Samuel S., and Jeffrey J. Warren. "Syntheses, characterization, and electrochemical behavior of alkylated 2-(2′-quinolylbenzimidazole) complexes of rhenium (I)." Canadian Journal of Chemistry 96, no. 2 (2018): 119–23. http://dx.doi.org/10.1139/cjc-2017-0320.

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A series of ClRe(CO)3-containing complexes with 1-methyl-1H-benzo[d]imidazol-2-yl)quinoline (Me-QuBIm), 1-benzyl-1H-benzo[d]imidazol-2-yl)quinoline (Bn-QuBIm), and 2-(1-(4-methoxybenzyl)-1H-benzo[d]imidazol-2-yl)quinoline (OMeBn-QuBIm) ligands were prepared and characterized. Each complex was characterized using 1H and 13C NMR, infrared, UV–vis, and fluorescence spectroscopies, and cyclic voltammetry. The physical properties of each complex are similar to the parent ClRe(CO)3(2-(1H-benzo[d]imidazol-2-yl)quinoline) complex. However, the electrochemical behavior is distinct from the parent, showing reversible voltammograms and poor CO2 reduction activity. Addition of K+ or Mg2+ as Lewis acids modestly increases catalytic currents, but at large overpotentials. The work presented here is consistent with a mechanism that involves rhenium reduction and deprotonation of imidazole and benzimidazole prior to CO2 reduction electrocatalysis.

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Layla Amer Ibrahim and Radhiyah Abdul Baqi Aldujaili. "Synthesis , Characterization and study the Antimicrobial Activity For Benzo pyran -2-imine and Tetrazole Ring Derivatives." Journal of Kufa for Chemical Sciences 3, no. 3 (2024): 178–200. https://doi.org/10.36329/jkcm/2024/v3.i3.15835.

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The derivatives of [3-(1H-benzo[d]imidazol-2-yl)-2H-chromen-2-imine]L8 and [2-((1H-tetrazol-5-yl)methyl)-1H-benzo[d]imidazole] L7,L9 have been obtained using -(1H-benzo[d]imidazol-2-yl)acetonitrile as starting material .The latter compound was utilized as a key intermediate for the synthesis of new heterocyclic compounds L8,7,9 with good yields. Newly synthesized compounds have been screened for their antimicrobial activity and characterized by analytical and spectral data.

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21

Mlostoń, Grzegorz, Małgorzata Celeda, Marcin Jasiński, et al. "2-Unsubstituted Imidazole N-Oxides as Novel Precursors of Chiral 3-Alkoxyimidazol-2-ylidenes Derived from trans-1,2-Diaminocyclohexane and Other Chiral Amino Compounds." Molecules 24, no. 23 (2019): 4398. http://dx.doi.org/10.3390/molecules24234398.

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‘Desymmetrization’ of trans-1,2-diaminocyclohexane by treatment with α,ω-dihalogenated alkylation reagents leads to mono-NH2 derivatives (‘primary-tertiary diamines’). Upon reaction with formaldehyde, these products formed monomeric formaldimines. Subsequently, reactions of the formaldimines with α-hydroxyiminoketones led to the corresponding 2-unsubstituted imidazole N-oxide derivatives, which were used here as new substrates for the in situ generation of chiral imidazol-2-ylidenes. Upon O-selective benzylation, new chiral imidazolium salts were obtained, which were deprotonated by treatment with triethylamine in the presence of elemental sulfur. Under these conditions, the intermediate imidazol-2-ylidenes were trapped by elemental sulfur, yielding the corresponding chiral non-enolizable imidazole-2-thiones in good yields. Analogous reaction sequences, starting with imidazole N-oxides derived from enantiopure primary amines, amino alcohols, and amino acids, leading to the corresponding 3-alkoxyimidazole-2-thiones were also studied.

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22

Xu, Guo-Wang, Ye-Nan Wang, Hai-Bing Wang та Zhong-Long Wang. "Crystal structure ofcatena-poly[[diaquacobalt(II)]-bis[μ-5-(4-carboxyylatophenyl)picolinato]-κ3N,O2:O5;κ3O5:N,O2-[diaquacobalt(II)]-μ-1-[4-(1H-imidazol-1-yl)phenyl]-1H-imidazole-κ2N3:N3′]". Acta Crystallographica Section E Crystallographic Communications 71, № 7 (2015): m145—m146. http://dx.doi.org/10.1107/s2056989015012190.

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The asymmetric unit of the title polymeric CoIIcomplex, [Co2(C13H7NO4)2(C12H10N4)(H2O)4]n, contains a CoIIcation, a 5-(4-carboxylatophenyl)picolinate dianion, two coordination water molecules and half of 1-[4-(1H-imidazol-1-yl)phenyl]-1H-imidazole ligand. The CoIIcation is coordinated by two picolinate dianions, two water molecules and one 1-[4-(1H-imidazol-1-yl)phenyl]-1H-imidazole molecule in a distorted N2O4octahedral coordination geometry. The two picolinate dianions are related by an inversion centre and link two CoIIcations, forming a binuclear unit, which is further bridged by the imidazole molecules, located about an inversion centre, into the polymeric chain propagating along the [-1-11] direction. In the crystal, the three-dimensional supramolecular architecture is constructed by O—H...O hydrogen bonds between the coordinating water molecules and the non-coordinating carboxylate O atoms of adjacent polymeric chains.

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23

Tan, Fen, Zheng-Zheng Meng, Xiao-Qin Xiong, Guo-Ping Zeng, and Ming-Wu Ding. "One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes." Synlett 30, no. 07 (2019): 857–59. http://dx.doi.org/10.1055/s-0037-1611760.

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A new, one-pot, regioselective preparation of 2,5,6,7-tetrahydroimidazo[1,2-a]imidazol-3-ones by a sequential aza-Wittig/nucleophilic addition/cyclization reaction was developed. The aza-Wittig reactions of ethyl (2Z)-3-aryl-2-[(triphenylphosphoranylidene)amino] acrylates with aryl isocyanates produced carbodiimide intermediates that were then treated sequentially with 2-aminoethanol and tosyl chloride/triethylamine to give the corresponding (2Z)-2-[(substituted)benzylidene]-2,5,6,7-tetrahydro-3H-imidazo[1,2-a]imidazol-3-ones in good overall yields and with high regioselectivity.

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24

Vedekhina, T. S., M. V. Chudinov, and A. Yu Lukin. "Design and synthesis of 4-nitroimidazole derivatives with potential antitubercular activity." Fine Chemical Technologies 18, no. 3 (2023): 219–29. http://dx.doi.org/10.32362/2410-6593-2023-18-3-219-229.

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Objectives. To develop the procedures for synthesis of hybrid molecules with potential anti-tubercular activity containing heterocyclic cores of 4-nitroimidazole and 1,3,4-thiadiazole within the framework of a double-drug strategy and predict bioactivity of target structures and drug-likeness physicochemical parameters.Methods. Target compounds were prepared by classical organic synthesis methods. The structure of the obtained compounds was characterized by melting points, 1H and 13C nuclear magnetic resonance spectroscopy, and high-resolution mass spectrometry. The calculation of the physicochemical parameters of the target compounds and prediction of their biological activity were carried out using publicly available software for cheminformatics and molecular modeling.Results. Acylation of propargylamine with (2-methyl-4-nitro-1H-imidazol-1-yl)acetic and (4-nitro-1H-imidazol-1-yl)acetic acids provided the corresponding amides, which were cyclized with seven different benzylamines in the presence of zinc triflate. In this way, seven new compounds were obtained at 20–30% yields. Ten arylamines were acylated with chloroacetyl chloride and the resulting chloroacetamides were converted into corresponding thio-oxahydrazides by the Willgerodt–Kindler reaction. Following acylation by (4-nitro-1H-imidazol-1-yl)acetic acid, these compounds were converted into the target hybrid imidazolyl-thiadiazoles at 29–54% yields.Conclusions. Two series of new heterocyclic compounds with a hybrid structure including a privileged 4-nitroimidazole moiety linked to the second heterocycle, imidazole, or thiadiazole, were obtained. The synthesis and characterization of compounds by physicochemical methods was aimed at searching for anti-tuberculosis activity. The bioactivity potential of target compounds was demonstrated by preliminary calculations performed using public prognostic programs.

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Rufaida, Farheen *. Y. Rajesh Babu 1. "SYNTHESIS AND CHEMICAL CHARACTERIZATION OF BENZIMIDAZOLE FUSED BENZOPYRAN DERIVATIVES AND EVALUATION OF THEIR ANTI-BACTERIAL POTENCY." Journal of Pharma Research 8, no. 3 (2019): 88–93. https://doi.org/10.5281/zenodo.2620330.

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ABSTRACT Benz-imidazole fused benzopyran derivatives were prepared by the reaction of 2-(1H-Benzo[d]Imidazol-2-yl)-1phenyl-1H-Benzo[f]chromeno-3-amine with different substituted benzaldehydes. The resulting derivatives were subjected to physical and chemical characterization. The anti-bacterial potency of the synthesized compounds was tested against a set of Gram positive and negative bacteria. The compound 9-(2-methoxyphenyl)-16-phenyl-16H-benzo[4,5]imidazo[1,2-c]benzo[5,6]chromeno[3,2-e]pyrimidine exhibited most potent activity. Detailed toxicological studies and molecular modelling would be beneficial in developing new drugs. KEYWORDS: Benzimidazole, Benzopyran, Coumarin, Anti-Bacterial, Disc-Diffusion.

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26

Takaki, Reina, and Bradley O. Ashburn. "(E)-3-[4-(1H-Imidazol-1-yl)phenyl]-1-(3-chloro-4-fluorophenyl)prop-2-en-1-one." Molbank 2022, no. 2 (2022): M1375. http://dx.doi.org/10.3390/m1375.

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Imidazole-containing chalcones have been shown to be effective against Aspergillus fumigatus, the pathogenic agent for pulmonary aspergillosis. Claisen-Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 3′-chloro-4′-fluoroacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(3-chloro-4-fluorophenyl)prop-2-en-1-one in good purity after purification by silica gel column chromatography. This novel compound is suitable for testing the antifungal properties of the combined pharmacophores against Aspergillus and other pathogenic fungi.

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27

Bailey, Nicholas, and Bradley O. Ashburn. "(E)-3-[4-(1H-Imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one." Molbank 2021, no. 3 (2021): M1269. http://dx.doi.org/10.3390/m1269.

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Imidazole-containing chalcones have been shown to be strongly effective against Aspergillusfumigatus, the causative agent for the disease pulmonary aspergillosis. Claisen–Schmidt condensation of 4-(1H-imidazol-1-yl)benzaldehyde with 4′-methylacetophenone using aqueous sodium hydroxide in methanol yielded the novel compound (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one in good yield and purity after recrystallization from hot methanol. With the known antifungal properties of these combined pharmacophores, this novel compound is suitable for anti-aspergillus activity study.

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Xu, Wei, Hao Yao, Xing Zhang, et al. "K2CO3 Promoted Cascade Reaction for the Preparation of 1H-Imidazol-4- yl-1-amine Derivatives." Letters in Organic Chemistry 17, no. 2 (2020): 127–32. http://dx.doi.org/10.2174/1570178616666190226144620.

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: A K2CO3 promoted efficient one pot two-step method for the preparation of 1H-imidazol-4- yl-1-amine derivatives has been developed. A series of second amines with an imidazole group were obtained with 56%-91% yields by the K2CO3 promoted amination of acetates and nitrogen deprotection of the imidazole process.

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29

Ashok, S. R., and M. K. Shivananda. "Synthesis and Characterization and Antifungal Screening Studies of Some Novel Imidazole Derivatives." 1 8, no. 1 (2022): 39–43. http://dx.doi.org/10.46632/jemm/8/1/7.

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Imidazole derivatives are five-mamboed heterocyclic having nitrogen, and oxygen atoms in their ring structure and exhibiting potent as well as wide range of pharmacological activities. Current investigations of imidazole derivatives have provided information that these derivatives may have applications in antimicrobial, antifungal, antiviral, as well as antidiabitic treatments. Fen bam is an imidazole derivative developed by McNeil Laboratories in the late 1970s as a novel anxiolytic drug with an at-the-time-unidentified molecular target in the brain. The imidazole ring system is present in important biological building blocks such as histamine, and the related hormone histamine. Imidazole can serve as a base and as a weak acid. Many antifungal drugs such as nitroimidazole contain an imidazole ring. Thus, varied pharmacological activities of 2-amino-1-methyl-1H-imidazol-4(5H)-one derivatives have encouraged us to design and synthesize some of new class of heterocycles containing imidazolering and its derivatives. Different isomeric secondary amine containing bicyclical aromatic heterocyclic compounds were treated with 2-amino1-methyl-1H-imidazol-4(5H)-one in presence of base by using DMF as solvent and HBTU as coupling agent to get target compounds. Pure target compounds were characterized by 1H NMR, 13C NMR and LC-MS. Some of the selected imidazole derivatives were screened for their antifungal activities.

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30

Lettau, Herbert, and Hans Jürgen Heckel. "Imidazol-N-oxide; Reaktion von Imidazolen und Imidazol-N-oxiden mit Dibenzoylperoxid." Zeitschrift für Chemie 11, no. 2 (2010): 62–63. http://dx.doi.org/10.1002/zfch.19710110208.

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31

Ahmad, Muhammad Saeed, Abu Bakar Siddique, Muhammad Khalid, et al. "Synthesis, antioxidant activity, antimicrobial efficacy and molecular docking studies of 4-chloro-2-(1-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazol-2-yl)phenol and its transition metal complexes." RSC Advances 13, no. 14 (2023): 9222–30. http://dx.doi.org/10.1039/d2ra08327b.

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Herein, a one-pot synthesis of tetra-substituted imidazole, 4-chloro-2-(1-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazol-2-yl)phenol (HL), is reported by the reaction of benzil, 5-chlorosalicylaldehyde, ammonium acetate and anisidine.

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32

Tarai, Arup, and Jubaraj B. Baruah. "Competing phenol–imidazole and phenol–phenol interactions in the flexible supramolecular environment of N,N′-bis(3-imidazol-1-ylpropyl)naphthalenediimide causing domain expansion." New Journal of Chemistry 41, no. 19 (2017): 10750–60. http://dx.doi.org/10.1039/c7nj02322g.

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Spectroscopic and crystallographic studies on cocrystals of N,N′-bis(3-imidazol-1-yl-propyl)naphthalenediimide (L) with a series of phenolic compounds have revealed that competition to form phenol–imidazole and phenol–phenol synthons causes domain expansion.

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33

Akhtar, Mansoor, Ali Muhammad Arif, Shifa Ullah Khan, Guo-Gang Shan, Hong-liang Xu, and Zhong-Min Su. "Tuning the NLO response of bis-cyclometalated iridium(iii) complexes by modifying ligands: experimental and structural DFT analysis." New Journal of Chemistry 45, no. 12 (2021): 5491–96. http://dx.doi.org/10.1039/d1nj00114k.

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DFT calculations have been carried out to investigate two synthesized iridium(iii) complexes with substituted Phbd (1-phenyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole) and Crbd (9-(4-(2-(pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)-9H-carbazole) as ancillary ligands.

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34

Arulmurugan, Subramaniyan, and Helen P. Kavitha. "Synthesis and potential cytotoxic activity of some new benzoxazoles, imidazoles, benzimidazoles and tetrazoles." Acta Pharmaceutica 63, no. 2 (2013): 253–64. http://dx.doi.org/10.2478/acph-2013-0018.

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2 The present work deals with the synthesis of some novel heterocyclic compounds such as benzoxazoles , 7, 13 and 19, imidazoles 3, 8, 14 and 20, benzimidazoles 4, 9, 15 and 21, and tetrazoles 10, 16, and 22. The synthesized compounds were characterized by IR, 1H NMR, mass spectrometry and elemental analysis. The compounds were evaluated for cytotoxicity against human cancer cell lines such as MCF-7 (breast cancer) and HT-29 (colon cancer) by the MTT assay method. Among the tested compounds, 4,4’-sulfonylbis(N-(2-(1H-benzo[d]imidazol- -2-yl)ethyl)aniline (9), N-bis(2-(benzo[d]oxazol-2-yl)-ethyl)- 6-phenyl-1,3,5-triazine-2,4-diamine (13), N-bis(2-(1H-benzo[ d]imidazol-2-yl)ethyl)-6-phenyl-1,3,5-triazine-2,4-diamine (15) and N-tris(2-1H-benzo[d]imidazol-2-yl)ethyl)- 1,3,5-triazine-2,4,6-triamine (21) showed potent cytotoxicity.

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35

Koudjina, Simplice, John A. Agwupuye, Terkumbur E. Gber, et al. "Mechanistic Molecular Insights and Quantum Biological Properties of Methyl-Imidazole Derivatives as Potential Anticancer Agents." Asian Journal of Chemistry 37, no. 5 (2025): 1211–23. https://doi.org/10.14233/ajchem.2025.33290.

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Methyl-imidazole derivatives are attracting considerable scientific attention because of their extensive and significant bioactivities. Hence, this work focuses on the investigation of the geometry, frontier molecular orbitals (FMOs), HOMO-LUMO energy gap, molecular docking, bioavailability, ADMET and pharmacokinetic properties of 1-(4-methoxyphenyl)-2,4,5-trimethyl-1H-imidazole (M1), 4-(4,5-dimethyl-1H-imidazol-1-yl)benzenesulfonic acid (M2), N-hydroxy-N-(4-(2,4,6-trimethyl-1H-imidazol-1-yl)phenyl)hydroxylamine (M3) and 2,4,5-trimethyl-1H-imidazole (M4) respectively, utilizing DFT at 6-311++g(d,p) basis set with different functionals viz. B3LYP, B3PW91, M062X, PBE0 and ωB967XD. A high-level quantum computational study and molecular docking were performed to ascertain the stability, reactivity and drug likeness of the titled molecules. Especially, compound M2 had the least energy gap (3.92 eV) and its reactivity can be explained based on the attached sulphonic substituent compared to M1, M3 and M4, respectively. Interestingly, the studied compounds showed good biological activities against various cancer proteins with PDB IDs 3F66, 4XVE, 1XF0 and 5Y8Y. The studied molecules present a valuable opportunity for developing cancer drugs with improved therapeutic indices.

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Gerasimova, Elena L., Elena R. Gazizullina, Maria V. Borisova, et al. "Design and Antioxidant Properties of Bifunctional 2H-Imidazole-Derived Phenolic Compounds—A New Family of Effective Inhibitors for Oxidative Stress-Associated Destructive Processes." Molecules 26, no. 21 (2021): 6534. http://dx.doi.org/10.3390/molecules26216534.

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The synthesis of inhibitors for oxidative stress-associated destructive processes based on 2H-imidazole-derived phenolic compounds affording the bifunctional 2H-imidazole-derived phenolic compounds in good-to-excellent yields was reported. In particular, a series of bifunctional organic molecules of the 5-aryl-2H-imidazole family of various architectures bearing both electron-donating and electron-withdrawing substituents in the aryl fragment along with the different arrangements of the hydroxy groups in the polyphenol moiety, namely derivatives of phloroglucinol, pyrogallol, hydroxyquinol, including previously unknown water-soluble molecules, were studied. The structural and antioxidant properties of these bifunctional 5-aryl-2H-imidazoles were comprehensively studied. The redox transformations of the synthesized compounds were carried out. The integrated approach based on single and mixed mechanisms of antioxidant action, namely the AOC, ARC, Folin, and DPPH assays, were applied to estimate antioxidant activities. The relationship “structure-antioxidant properties” was established for each of the antioxidant action mechanisms. The conjugation effect was shown to result in a decrease in the mobility of the hydrogen atom, thus complicating the process of electron transfer in nearly all cases. On the contrary, the conjugation in imidazolyl substituted phloroglucinols was found to enhance their activity through the hydrogen transfer mechanism. Imidazole-derived polyphenolic compounds bearing the most electron-withdrawing functionality, namely the nitro group, were established to possess the higher values for both antioxidant and antiradical capacities. It was demonstrated that in the case of phloroglucinol derivatives, the conjugation effect resulted in a significant increase in the antiradical capacity (ARC) for a whole family of the considered 2H-imidazole-derived phenolic compounds in comparison with the corresponding unsubstituted phenols. Particularly, conjugation of the polyphenolic subunit with 2,2-dimethyl-5-(4-nitrophenyl)-2H-imidazol-4-yl fragment was shown to increase ARC from 2.26 to 5.16 (104 mol-eq/L). This means that the considered family of compounds is capable of exhibiting an antioxidant activity via transferring a hydrogen atom, exceeding the activity of known natural polyphenolic compounds.

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Oliveira, Ana P. A., Isabella P. Ferreira, Angel A. Recio Despaigne, et al. "Structural studies and antileishmanial activity of 2-acetylpyridine and 2-benzoylpyridine nitroimidazole-derived hydrazones." Acta Crystallographica Section C Structural Chemistry 75, no. 3 (2019): 320–28. http://dx.doi.org/10.1107/s2053229619001529.

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Three imidazole hydrazone compounds, namely 2-(4-nitro-1H-imidazol-1-yl)-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide, C12H12N6O3, (1), 2-(2-nitro-1H-imidazol-1-yl)-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide, C12H12N6O3, (2), and 2-(2-nitro-1H-imidazol-1-yl)-N′-[(phenyl)(pyridin-2-yl)methylidene]acetohydrazide, C17H14N6O3, (3), were obtained and fully characterized, including their crystal structure determinations. While all the compounds proved not to be cytotoxic to J774.A1 macrophage cells, (1) and (3) exhibited activity against Leishmania chagasi, whereas (2) was revealed to be inactive. Since both (1) and (3) exhibited antileishmanial effects, while (2) was devoid of activity, the presence of the acetyl or benzoyl groups was possibly not a determining factor in the observed antiprotozoal activity. In contrast, since (1) and (3) are 4-nitroimidazole derivatives and (2) is a 2-nitroimidazole-derived compound, the presence of the 4-nitro group probably favours antileishmanial activity over the 2-nitro group. The results suggested that further investigations on compounds (1) and (3) as bioreducible antileishmanial prodrug candidates are called for.

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Jin, Guo-Xia, Tian-Chao You, and Jian-Ping Ma. "Three AgI, CuI and CdII coordination polymers based on the new asymmetrical ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole: syntheses, characterization and emission properties." Acta Crystallographica Section C Structural Chemistry 75, no. 12 (2019): 1690–97. http://dx.doi.org/10.1107/s2053229619015663.

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The new asymmetrical organic ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole (L, C17H13N5O), containing pyridine and imidazole terminal groups, as well as potential oxdiazole coordination sites, was designed and synthesized. The coordination chemistry of L with soft AgI, CuI and CdII metal ions was investigated and three new coordination polymers (CPs), namely, catena-poly[[silver(I)-μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole] hexafluoridophosphate], {[Ag(L)]PF6} n , catena-poly[[copper(I)-di-μ-iodido-copper(I)-bis(μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)] 1,4-dioxane monosolvate], {[Cu2I2(L)2]·C4H8O2} n , and catena-poly[[[dinitratocopper(II)]-bis(μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)]–methanol–water (1/1/0.65)], {[Cd(L)2(NO3)2]·2CH4O·0.65H2O} n , were obtained. The experimental results show that ligand L coordinates easily with linear AgI, tetrahedral CuI and octahedral CdII metal atoms to form one-dimensional polymeric structures. The intermediate oxadiazole ring does not participate in the coordination interactions with the metal ions. In all three CPs, weak π–π interactions between the nearly coplanar pyridine, oxadiazole and benzene rings play an important role in the packing of the polymeric chains.

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Kinuta, M., T. Ubuka, W. B. Yao, Y. Q. Zhao, and H. Shimizu. "Isolation of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiolactic acid, a new metabolite of histidine, from normal human urine and its formation from S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine." Biochemical Journal 297, no. 3 (1994): 475–78. http://dx.doi.org/10.1042/bj2970475.

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S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiolactic acid (CIE-TL), a novel imidazole compound with a sulphur-containing side chain, was isolated from normal human urine by ion-exchange column chromatography, and characterized by physicochemical analyses involving m.s., i.r. spectrophotometry, high-voltage paper electrophoresis and elemental analysis as well as chemical synthesis. CIE-TL was synthesized by the reaction of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]cysteine (CIE-Cys) with NaNO2 in HCl. CIE-TL was also formed during enzymic degradation of CIE-Cys by rat liver or kidney homogenate in a phosphate buffer, possibly via the metabolic intermediate S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-thiopyruvic acid, and this was accompanied by the formation of 3-[(carboxymethyl)thio]-3-(1H-imidazol-4-yl)propanoic acid, a compound previously found in human urine [Kinuta, Yao, Masuoka, Ohta, Teraoka and Ubuka (1991) Biochem. J. 275, 617-621]. These results suggest that CIE-Cys [Kinuta, Ubuka, Yao, Futani, Fujiwara and Kurozumi (1992) Biochem. J. 283, 39-40] is a physiological precursor of the urinary compounds and that L-histidine is metabolized in part via an alternative pathway initiated by the adduction of natural thiol compounds such as cysteine and GSH to urocanic acid, the first catabolite of histidine.

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40

Sreenivasa Rao, Ramana, Femil Joseph Shajan, and D. Srinivasa Reddy. "A route to access imidazol[1,5-a]indole-1,3-diones and pyrrolo[1,2-c]imidazole-1,3-diones." Organic & Biomolecular Chemistry 17, no. 36 (2019): 8384–90. http://dx.doi.org/10.1039/c9ob01462d.

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A simple and practical method for synthesizing imidazol[1,5-a]indoles and pyrrolo[1,2-c]imidazoles has been developed. The present method uses microwave conditions and is free from the need for work-up and column chromatography.

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41

Al-Soud, Yaseen, Najim Al-Masoudi, Hamed Hassan, Erik De Clercq, and Christophe Pannecouque. "Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives." Acta Pharmaceutica 57, no. 4 (2007): 379–93. http://dx.doi.org/10.2478/v10007-007-0031-7.

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Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivativesA series of 2-alkylthio-1-[4-(1-benzyl-2-ethyl-4-nitro-1H- -imidazol-5-yl)-piperazin-1-y]lethanones (3-9) and alkyl- [4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)-piperazin- -1-yl)ketones (11-20) as well as the indole analogue22were synthesized from 4-nitro-5-piperazinyl imidazole derivative1, with the aim to develop newly non-nucleoside reverse transcriptase inhibitors (NNRTIs). The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compound2showed inhibition of HIV-1 (EC50 0.45 mg mL-1) and HIV-2 (0.50 mg mL-1), while9showed inhibition of HIV-1 (EC502.48 mg mL-1, SI = 4).

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Poyraz, Mehmet, та Musa Sarı. "Crystal structure ofcatena-poly[[bis(acetato-κO)copper(II)]-bis[μ-4-(1H-imidazol-1-yl)phenol]-κ2N3:O;κ2O:N3]". Acta Crystallographica Section E Crystallographic Communications 73, № 2 (2017): 209–12. http://dx.doi.org/10.1107/s2056989017000780.

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In the title compound, [Cu(CH3COO)2(C9H8N2O)2]n, the CuIIion resides on a centre of inversion, displaying a tetragonally distorted octahedral coordination environment defined by two pairs of N and O atoms of symmetry-related 4-(1H-imidazol-1-yl)phenol ligands and the O atoms of two symmetry-related acetate ligands. The bridging mode of the 4-(1H-imidazol-1-yl)phenol ligands is associated with a very long Cu...O interactions involving the phenol O atom of the heterocyclic ligand, which creates chains extending parallel to [100]. In the crystal, the chains are arranged in a distorted hexagonal rod packing and are linkedviaC—H...O hydrogen bonds and by π–π stacking interactions involving centrosymmetrically related pairs of imidazole and phenol rings.

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43

Chen, Hong, та Heng Xu. "Poly[(μ2-benzene-1,3-dicarboxylato-κ2 O 1:O 3){μ2-1,2-bis[(1H-imidazol-1-yl)methyl]benzene-κ2 N 3:N 3′}zinc]". Acta Crystallographica Section E Structure Reports Online 68, № 6 (2012): m826. http://dx.doi.org/10.1107/s1600536812022544.

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In the two-dimensional title coordination polymer, [Zn(C8H4O4)(C14H14N4)] n , the ZnII atom adopts a distorted tetrahedral geometry, being ligated by two O atoms from two different benzene-1,3-dicarboxylate dianions and two N atoms from two symmetry-related 1,2-bis(imidazol-1-ylmethyl)benzene molecules. The dihedral angles between the imidazole rings and the benzene ring in the neutral ligand are 76.31 (13) and 85.33 (15)°. The ZnII atoms are bridged by dicarboxylate ligands, forming chains parallel to the a axis, which are further linked by 1,2-bis(imidazol-1-ylmethyl)benzene molecules, generating a two-dimensional layer structure parallel to the ac plane. The crystal structure is enforced by intralayer and interlayer C—H...O hydrogen bonds.

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44

Feizbakhsh Bazargani, Mona, Laleh Talavat, Soheila Naderi, and Hamid Reza Khavasi. "2-[(1H-Imidazol-2-yl)disulfanyl]-1H-imidazole." Acta Crystallographica Section E Structure Reports Online 67, no. 10 (2011): o2585. http://dx.doi.org/10.1107/s1600536811036014.

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Lettau, Herbert. "Imidazol-N-oxide; Eine einfache Synthese substituierter Imidazole." Zeitschrift für Chemie 11, no. 1 (2010): 10–11. http://dx.doi.org/10.1002/zfch.19710110104.

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46

Saldaña Arredondo, Cristian, Karla A. González Pérez, Jorge Alejandro Tovar Rosales, and María del Rocío Gámez Montaño. "Síntesis verde de imidazo[2,1-b]tiazoles vía Groebke-Blackburn-Bienaymé asistida por microondas." JÓVENES EN LA CIENCIA 28 (October 2, 2024): 1–7. https://doi.org/10.15174/jc.2024.4314.

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Se sintetizó una serie de imidazo[2,1-b]tiazoles a través de un proceso multicomponente, mediante la reacción Groebke-Blackburn-Bienaymé (GBB) en microondas. Los imidazotiazoles sintetizados contienen en su estructura los núcleos de imidazol y tiazol, los cuales se encuentran presentes en una variedad de compuestos bioactivos y fármacos.

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47

Bremer, Johannes, Stefan Uhlenbrock, A. Alan Pinkerton, and Bernt Krebs. "Zink-Koordinationsverbindungen mit Imidazolin- und Imidazol-Donorliganden." Zeitschrift f�r anorganische und allgemeine Chemie 619, no. 7 (1993): 1183–95. http://dx.doi.org/10.1002/zaac.19936190707.

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48

Naz, Nimra, Saima Saqib, Rizwan Ashraf, Muhammad Irfan Majeed, and Muhammad Adnan Iqbal. "Synthesis of New Organoselenium Compounds: Characterization and Biological Studies." Macedonian Journal of Chemistry and Chemical Engineering 39, no. 1 (2020): 1. http://dx.doi.org/10.20450/mjcce.2020.1912.

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Two new organoselenium analogs, (3,3'-(1,2-phenylenebis(methylene))bis(2-selenoxo-2,3-dihydro-1H-imidazole-3,1-diyl))bis(methylene) dibenzoate (III) and 3,3'-(1,2-phenylenebis(methylene))bis(1-benzyl-1H-imidazole-2(3H)-selenone) (V), were derived from newly synthesized organic salts 1,1'-(1,2-phenylenebis(methylene))bis(3-(2-phenoxyacetyl)-1H-imidazol-3-ium) chloride (II) and 1,1'-(1,2-phenylenebis(methylene))bis(3-benzyl-1H-imidazol-3-ium) chloride (IV), and each was characterized by various analytical techniques, such as Fourier-Transform Infrared Spectroscopy (FT-IR), UV–visible, and Nuclear Magnetic Resonance (NMR) spectroscopy, as well as Ultra-high performance liquid chromatography mass spectrometry/Photodiode array (UHPL-MS/PDA). All synthesized compounds were tested for their antioxidant and anticancer potential. Very good radical scavenging results were obtained for salts II and IV, with cell viability values of 84.6±3.5 and 56.7±5.5%, respectively, compared to their organoselenium adducts. All synthesized products showed significant activity against MCF-7 breast cancer cells, but compounds II and III showed better results, with cell viability values of 40.5±2.0% and 34.4±1.5%, respectively.

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Aly, Ashraf A. "Base Catalyzed Synthesis of Novel Fused-Imidazoles from N-Vinyl-1H-imidazole." Zeitschrift für Naturforschung B 60, no. 1 (2005): 106–12. http://dx.doi.org/10.1515/znb-2005-0116.

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Syntheses of various classes of fused-imidazoles are reported. The key to their successful synthesis depends on the reaction of N-vinyl-1H-imidazole with the π-deficient compounds under basic conditions. Reaction of the target imidazole with 1,1,2,2-tetracyanoethylene and dimethyl acetylenedicarboxylate afforded pyrrolo[1,2-a]imidazoles. On the other site, reaction of the target imidazole with 2-dicyanomethyleneindane-1,3-dione, 2,3-dicyano-1,4-naphthoquinone gave indanylimidazolo- [1,2-a]azepine and imidazolo[2,1-a]phenanthridine derivatives, respectively. Under basic reaction condition, various classes of imidazolo[2,1-a]isoquinolines were obtained by the reaction of N-vinyl- 1H-imidazole with 2,3,5,6-tetrachloro-1,4-benzoquinone, 2,3-dichloro-1,4-naphthoquinone, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 3,4,5,6-tetrachloro-1,2-benzoquinone.

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Quinlivan, Patrick J., Ja-Shin Wu, and Rita K. Upmacis. "Crystal structure of metronidazolium tetrachloridoaurate(III)." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (2015): 810–12. http://dx.doi.org/10.1107/s2056989015010798.

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Metronidazole (MET) [systematic names: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol] is a medication that is used to treat infections from a variety of anaerobic organisms. As with other imidazole derivatives, metronidazole is also susceptible to protonation. However, there are few reports of the structures of metronidazolium derivatives. In the title compound, (C6H10N3O3)[AuCl4] [systematic name: 1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazol-3-ium tetrachloridoaurate(III)], the asymmetric unit consists of a metronidazolium cation, [H(MET)]+, and a tetrachloridoaurate(III) anion, [AuCl4]−, in which the AuIIIion is in a slightly distorted square-planar coordination environment. In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O...;N—C=C torsion angle of −0.2 (4)°, while the hydroxyethyl group is in a coiled conformation, with an O(H)—C—C—N torsion angle of 62.3 (3)°. In the crystal, the anion and cation are linked by an intermolecular O—H...Cl hydrogen bond. In addition, the N—H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hydroxyethyl group of a symmetry-related molecule, leading to the formation of chains along [010].

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Journal articles on the topic 'Imidazol'

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