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Journal articles on the topic 'Benzimidazoles – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Al-Warhi, Tarfah, Mohamed Said, Mahmoud El Hassab, Nada Aljaeed, Hazem Ghabour, Hadia Almahli, Wagdy Eldehna, and Hatem Abdel-Aziz. "Unexpected Synthesis, Single-Crystal X-ray Structure, Anticancer Activity, and Molecular Docking Studies of Certain 2–((Imidazole/Benzimidazol–2–yl)thio)–1–arylethanones." Crystals 10, no. 6 (May 31, 2020): 446. http://dx.doi.org/10.3390/cryst10060446.

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In connection with our research program concerning development of novel effective benzimidazole-based anticancer candidates, herein we describe a new unexpected synthetic route to obtain a series of 2–((imidazole/benzimidazol2–yl)thio)1–arylethanones endowed with promising anti-breast cancer and Cyclin-dependent kinase 2 (CDK2) inhibitory activities. Contrary to expectations, products for the reaction of 2–mercaptoimidazole/benzimidazole 2a,b with β–keto esters 6a–c were unambiguously assigned as 2–((imidazol/benzimidazol2–yl)thio)1–arylethanones 10a–f based on NMR spectroscopy and single-crystal X-ray crystallographic analyses. In vitro anticancer activities for herein reported imidazole/benzimidazoles 10a–f were assessed through a cell-based assay against human breast cancer T4–7D and MCF–7 cell lines. Benzimidazoles 10d–f exerted better anti-proliferative action towards T4–7D and MCF–7 cell lines than their corresponding imidazole counterparts 10a–c. Furthermore, a molecular docking study suggested CDK2 kinase as a potential enzymatic target for benzimidazoles 10d–f, and investigated their possible binding pattern and interactions within CDK2 active site. Thereafter, benzimidazoles 10d–f were in vitro examined for their CDK2 inhibitory action, where they exerted good activity. Finally, several key ADME and druglikeness properties were predicted by the SwissADME online tool. Interestingly, benzimidazoles 10d–f were found to have no violations in all druglikeness rules (Veber, Lipinski, Ghose, Muegge, and Egan). In addition, they had neither PAINS nor structural alerts (Brenks). In conclusion, benzimidazoles 10d–f demonstrated not only a promising anticancer activities but also an acceptable ADME and physicochemical properties especially benzimidazole 10e.

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2

Krishnamurthy, Naik, and Narashimaiah Shashikala. "Synthesis of ruthenium(II) carbonyl complexes with 2-monosubstituted and 1,2-disubstituted benzimidazoles." Journal of the Serbian Chemical Society 74, no. 10 (2009): 1085–96. http://dx.doi.org/10.2298/jsc0910085k.

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The reaction of the polymeric carbonyl complex [RuCl2(CO)2]x with 2-monosubstituted and 1,2-disubstituted benzimidazoles and 1,4-bis(benzimidazol- 2-yl)benzene (L9) in 2-methoxyethanol produces various coloured complexes of the formulae [Ru(CO)2Cl2(L)2]?xH2O (L = 1-(o-hydroxybenzyl)-2-(o-hydroxyphenyl)benzimidazole (L1), 1-(o-hydroxyphenyl)benzimidazole (L4), 1-(p-hydroxyphenyl)benzimidazole (L5), 1-(p-chlorobenzyl)-2-p-chlorophenyl) benzimidazole (L7), 1-[1-(dimethylamino)benzyl]-2-[1-(dimethylamino) phenyl]benzimidazole (L10), x = 0; L = 2-benzylbenzimidazole (L8), 1,4-bis(benzimidazol-2-yl)benzene (L9), x = 2; L = 1-(o-chlorobenzyl)-1-(o-chlorophenyl)benzimidazole (L6); x = 3), [Ru(CO)2Cl(L2)3]Cl?3H2O and [Ru(CO)2(L3)4]Cl2?3H2O (L2 = 1-(m-hydroxybenzyl)-2-(m-hydroxyphenyl)- benzimidazole; L3 = 1-(p-hydroxybenzyl)-2-(p-hydroxyphenyl)benzimidazole). The complexes were characterized by elemental analysis, conductivity measurements, as well as infrared, electronic, 1H- and 13C-NMR spectral studies.

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3

Sweeney, Martin, Darren Conboy, Styliana I. Mirallai, and Fawaz Aldabbagh. "Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles." Molecules 26, no. 9 (May 4, 2021): 2684. http://dx.doi.org/10.3390/molecules26092684.

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This review article provides a perspective on the synthesis of alicyclic and heterocyclic ring-fused benzimidazoles, imidazo[4,5-f]benzimidazoles, and imidazo[5,4-f]benzimidazoles. These heterocycles have a plethora of biological activities with the iminoquinone and quinone derivatives displaying potent bioreductive antitumor activity. Synthesis is categorized according to the cyclization reaction and mechanisms are detailed. Nitrobenzene reduction, cyclization of aryl amidines, lactams and isothiocyanates are described. Protocols include condensation, cross-dehydrogenative coupling with transition metal catalysis, annulation onto benzimidazole, often using CuI-catalysis, and radical cyclization with homolytic aromatic substitution. Many oxidative transformations are under metal-free conditions, including using thermal, photochemical, and electrochemical methods. Syntheses of diazole analogues of mitomycin C derivatives are described. Traditional oxidations of o-(cycloamino)anilines using peroxides in acid via the t-amino effect remain popular.

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4

Wang, Cheng Jun, De Yun Zeng, Shan Shan Gong, and Qi Sun. "An Unexpected Synthesis of 2H-Benzimidazole Derivatives." Advanced Materials Research 1023 (August 2014): 43–46. http://dx.doi.org/10.4028/www.scientific.net/amr.1023.43.

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Treatment of 1,2-phenylenediamines and 3-(N-phenyl-N-methyl) aminoacrolein with ZrCl4as catalyst in refluxing 95% ethanol afforded unexpected 2H-benzimidazole derivatives as the major products. It was determined that the formation of 2H-benzimidazoles was not from the decomposition of the 2-aminovinyl benzimidazoles.

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5

Begunov, Roman S., and Alexandr A. Sokolov. "SYNTHESIS AND MASS SPECTROMETRIC CHARACTERISTICS OF 1-(AMINOARYL)BENZIMIDAZOLES." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 9 (August 3, 2020): 12–20. http://dx.doi.org/10.6060/ivkkt.20206309.6230.

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As a result of two-stage synthesis, a number of 1-(aminoaryl)benzimidazoles, potential biologically active substances, were obtained. During the first stage, an aromatic nucleophilic substitution reaction, 2-R-benzimidazoles reacted with halogen-nitroarenes. The process proceeded under mild conditions, this indicates a good nucleophilic properties of benzimidazole. It has been shown that during reduction, depending on the structure of 1-(nitroaryl)benzimidazoles in an acidic medium, in addition to the main process, acid-catalyzed isomerization can occur. Rearrangement was observed during the reduction of 1-(2-nitroaryl)benzimidazoles. The presence of a methyl group at the 2 position of the benzimidazole ring of these compounds hindered the rearrangement. When carrying out the reaction under conditions of heterogeneous catalysis in the reactor for flow hydrogenation, isomerization was also not observed. The use of 1-(4-nitroaryl)benzimidazoles as a substrate resulted in the formation of only one product. The mass spectral characteristics of 1-(aminoaryl)benzimidazoles were studied. The peak attribution of the molecular ion [M]+ was carried out by recording mass spectra with electrospray ionization. Ways of fragmentation of the molecular ion of these compounds under the influence of electron impact are proposed. Characteristic ions are identified. It was established that the fragmentation of the molecular ion of 1-(aminoaryl)benzimidazoles began either by elimination of the substituents, followed by cleavage of the two C—N bonds in imidazole, or by elimination of the HCN fragment of the imidazole ring and further elimination of the substituents. As a result, the formation of the cation radical of N-phenylbenzenediamine with m/z 181 was occurred. The fragmentation of this ion was carried out similarly to aromatic amines via elimination of a neutral HCN molecule. Further decay of alkylarylamine ions led to a group of characteristic fragmentation ions. Thus, mass spectrometry can be effectively used to identify N-aryl substituted benzimidazoles, as well as their decomposition products.

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6

Andric, Deana, Gordana Tovilovic, Goran Roglic, Djurdjica Vaskovic, Vukic Soskic, Mirko Tomic, and Sladjana Kostic-Rajacic. "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl) piperazine derivatives." Journal of the Serbian Chemical Society 72, no. 5 (2007): 429–35. http://dx.doi.org/10.2298/jsc0705429a.

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Six newly synthesized heterocyclic (2-nitrophenyl)piperazines, with a specific structure of the heteroaryl group, whichmimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and _1 receptors. All compounds with a benzimidazole group had a 5-HT2A/D2 receptors binding ratio characteristic for atypical neuroleptics (>1, pK i values). Compound 7c, 4-bromo-6-{2-_4-(2-nitrophenyl)piperazin- 1-yl_ethyl}-1H-benzimidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations.

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7

Bektas, Hakan, Canan Albay, Emre Menteşe, Bahar Bilgin Sokmen, Zafer Kurt, and Dilem Şen. "Synthesis, Antioxidant and Antiurease Activities of Some New 5,6- dichloro-2-(4-fluorobenzyl)-1H-benzimidazole Derivatives Containing Furan, Oxadiazole, Triazole and Thiadiazole Moieties." Letters in Drug Design & Discovery 16, no. 8 (August 8, 2019): 939–47. http://dx.doi.org/10.2174/1570180815666180827124956.

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Background:Benzimidazoles and its derivatives have been attracting interest for many years because of their biological activities. Benzimidazoles containing different heterocyclic moieties have wide range of biological activities such as antimicrobial, antioxidant, anticancer, antiviral, etc.Methods:In this study, some benzimidazole derivatives containing furan, oxadiazole, triazole and thiadiazole moieties have been synthesized and then evaluated for their antioxidant and antiurease activities.Results:The results showed that all the tested benzimidazoles indicated remarkable urease inhibitory potentials with IC50 values ranging between 0.303±0.03 to 0.591±0.08 µM.Conclusion:In conclusion, synthesized benzimidazole derivatives showed good antioxidant and antiurease activities. Heterocyclic groups on benzimidazole nucleus enhance the activities.

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8

Barasa, Leonard, Hari P. Vemana, Nirupama Surubhotla, Sin S. Ha, Jing Kong, Alison Yong, John L. Croft, Vikas V. Dukhande, and Sabesan Yoganathan. "Synthesis and Biological Evaluation of Structurally Diverse Benzimidazole Scaffolds as Potential Chemotherapeutic Agents." Anti-Cancer Agents in Medicinal Chemistry 20, no. 3 (April 24, 2020): 301–14. http://dx.doi.org/10.2174/1871520619666191028101506.

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Background and Objective : Drug resistance and adverse effects are immense healthcare challenges in cancer therapy. Benzimidazole ring-based small molecules have been effective anticancer agents in drug development. In an effort to develop novel chemotherapeutics, we synthesized and assessed the anticancer and antibacterial activities of a small library of structurally unique benzimidazoles. Methods : The benzimidazoles were derived from indole, N-alkyl indole, fatty acid, and alpha-amino acid scaffolds providing a panel of diverse structures. The compounds were tested in three different cancer cell lines for cytotoxicity: HepG2 (human hepatocellular carcinoma), HeLa (human cervical carcinoma), and A549 (human lung carcinoma). Mechanism of cell death induced by benzimidazoles was evaluated using fluorescent dye-based apoptosis-necrosis assay, immunoblotting for active caspases, topoisomerase-II activity assay, and cell cycle assay. Results : Cell viability testing revealed that indole- and fatty acid-based benzimidazoles were most potent followed by the amino acid derivatives. Many compounds induced cytotoxicity in a concentration-dependent manner with cellular cytotoxicity (CC50) <20μM in the cell lines tested. Most compounds exhibited cytotoxicity via apoptosis through the intrinsic pathway. Inhibition of topoisomerase activity and cell cycle alterations were not the primary mechanisms of cytotoxicity. In addition, several compounds showed promising activity against S. aureus and S. epidermidis (Minimum Inhibitory Concentration (MIC) of as low as 0.04μmol/mL). Conclusion: The reported benzimidazole derivatives possess promising anticancer and antibacterial properties. Additionally, we discovered apoptosis to be the primary mechanism for cancer cell death induced by the tested benzimidazoles. Our findings suggest that further development of these scaffolds could provide drug leads towards new chemotherapeutics.

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9

Kapoor, Kamal, Parthasarathi Das, Rajni Khajuria, Sk Rasheed, and Chhavi Khajuria. "Recent Developments in the Synthesis of Pyrido[1,2-a]benzimidazoles." Synthesis 50, no. 11 (April 24, 2018): 2131–49. http://dx.doi.org/10.1055/s-0036-1589533.

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Pyrido[1,2-a]benzimidazole is one of the most important azaheterocyclic compounds consisting of three fused aromatic rings. Molecules containing this core have displayed a wide range of applications in the field of medicinal chemistry. The synthesis of pyrido[1,2-a]benzimidazole and its derivatives has attracted organic chemists because of its tremendous utility in interdisciplinary branches of chemistry. In this context, this review discusses the main advances in the synthesis of pyrido[1,2-a]benzimidazoles via metal-mediated and metal-free reactions from 2000 to 2016.1 Introduction2 Synthetic Approaches to Pyrido[1,2-a]benzimidazoles2.1 Type I: Transition-Metal-Catalyzed Methods2.2 Type II: Metal-Free Approaches3 Conclusion

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10

Ibrahim, Hassan K., Sayed H. El-Tamany, Reda F. El-Shaarawy, and Ibrahim M. El-Deen. "Synthesis and investigation of mass spectra of some novel benzimidazole derivatives." Macedonian Journal of Chemistry and Chemical Engineering 27, no. 1 (June 15, 2008): 65. http://dx.doi.org/10.20450/mjcce.2008.248.

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2-Substituted benzimidazoles (3) and (4a-c) were prepared via condensation of ethyl 2-thionyl-pyruvate (1) and hydrazidoyl derivatives (2a-c) with o-phenylene diamine in acetic acid. Acetylation of compound (4a) with acetic anhydride yielded the corresponding N-acetyl derivative (5). Treatment of compound 4b with hydrazine hydrate gave the corresponding hydrazino derivative (6). Reaction of 2-[(2-thionyl)acetyl)] benzimidazole (3) with hydrazine hydrate gave the pyrazolyl derivative (7) and hydrazino derivative (8). Alkylation of compound 3 with alkyl halide gave the corresponding 2,3-disubstituled benzimidazoles (9a, b). Pyrrolo[1,2-a] benzimidazole derivatives 10 and 11 were prepared via cyclocondensation of compound 3 with acetic anhydride in presence of AcONa and phosphorus oxychloride. The electron impact mass spectra of both of the above series of compounds have also been recorded and their fragmentation patterns are discussed.

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11

Janani, Marzieh, Masumeh Abdoli Senejani, and Tahereh Momeni Isfahani. "An Efficient Synthesis of Benzimidazole and Benzothiazole Derivatives Using a Nickel(II) Metal-Organic Framework." Current Organic Synthesis 17, no. 2 (May 8, 2020): 109–16. http://dx.doi.org/10.2174/1570179417666200117110758.

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Background: The benzimidazoles and benzothiazoles have shown relatively high pharmaceutical and biological activities. In recent years, numerous methods have been developed for synthesis of benzimidazole and benzothiazole derivatives using different catalysts. However, only some of the reported procedures are quite satisfactory and most of them have drawbacks. Herein, we report a convenient method for synthesis of benzimidazole and benzothiazole derivatives using a nickel (II) metal-organic framework (Ni- MOF) as a novel and reusable catalyst. The presence of unsaturated metal centers makes metal-organic frameworks to be used as Lewis acid catalysts. Objective: The primary objective of this study was to describe an efficient method for synthesis of benzimidazole and benzothiazole derivatives. Methods: Ni-MOF was prepared using the modified evaporation method and was characterized by FE-SEM, FT-IR, TGA, and XRD techniques.The catalyst was then used to test the synthesis of some benzimidazole and benzothiazole derivatives. The benzimidazoles and benzothiazoles were characterized by Elemental analyses, HNMR and IR techniques. Results: A variety of aromatic aldehydes bearing electron donating groups or electron-withdrawing were reacted with 1,2-phenylenediamine or 2-aminothiophenol using Ni-MOF in good to excellent yields. Conclusion: In summary, a new and highly efficient method was developed and reported for the synthesis of benzimidazole and benzothiazole derivatives using nickel(II) metal-organic framework. The advantages are short reaction times, good to excellent yields, the environmentally benign and simple procedure, stability, nontoxicity, recyclability, and easy separation of the catalyst.

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12

Rao, S. Srinivas, Ch Venkata Ramana Reddy, and P. K. Dubey. "Synthesis of N-Alkyl-2-thiomethyl Benzimidazoles: A Green Approach." Organic Chemistry International 2014 (March 17, 2014): 1–4. http://dx.doi.org/10.1155/2014/239710.

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A green approach for the synthesis of N-alkyl-2-thiomethyl benzimidazoles 2 (R=CH3, C2H5, CH2Ph) under different conditions has been developed from N-alkyl-2-chloromethyl benzimidazole (i.e., CH3, C2H5, CH2Ph) 1 by reaction with thiourea by physical grinding, or by using green solvents like ethanol and PEG-600, or by using microwave irradiation technique.

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13

Goossens, Laurence, Omar Castillo-Aguilera, Patrick Depreux, Alexia Ballée, Florian Beaurain, and Paola B. Arimondo. "Study of the Effect of Substituents of ortho-Phenylenediamines in the Opening of Lactones and Lactams for Access to Benzimidazol-2-yl Alkanols and Benzimidazol-2-yl Alkylamines." Synlett 31, no. 12 (May 15, 2020): 1216–20. http://dx.doi.org/10.1055/s-0040-1707112.

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Benzimidazoles represent common chemical moieties in bioactive compounds. The synthesis of this heterocycle often involves a condensation of an ortho-phenylenediamine with a carboxylic acid derivative. The observed dialkylation of the starting ortho-phenylenediamine is avoided by opening of lactones or lactams. This strategy can directly yield 1H-benzimidazoles substituted at the 2-position by a functionalized chain. We present herein a study of the effect of different electron-withdrawing or electron-donating groups at the 4-position of ortho-phenylenediamines on the opening of lactones or lactams to synthesize benzimidazol-2-yl alkanols and benzimidazol-2-yl alkylamines.

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14

Xie, Caixia, Xushuang Han, Jian Gong, Danyang Li, and Chen Ma. "One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5811–19. http://dx.doi.org/10.1039/c7ob00945c.

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A simple, one-pot and copper-catalyzed coupling reaction for the construction of 1,2-disubstituted benzimidazole derivatives is described. A low-cost copper salt and a weak base, K₃PO₄, were utilized in this reaction. A variety of 1,2-disubstituted benzimidazoles were obtained in moderate to excellent yields.

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15

Wang, Zhaozhan, Tao Song, and Yong Yang. "Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon." Synlett 30, no. 03 (January 14, 2019): 319–24. http://dx.doi.org/10.1055/s-0037-1610353.

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A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

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16

Kazimierczuk, Zygmunt, Jacqueline A. Upcroft, Peter Upcroft, Agata Górska, Bohdan Starościak, and Agnieszka Laudy. "Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives." Acta Biochimica Polonica 49, no. 1 (March 31, 2002): 185–95. http://dx.doi.org/10.18388/abp.2002_3835.

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Two series of benzimidazole derivatives were sythesised. The first one was based on 5,6-dinitrobenzimidazole, the second one comprises 2-thioalkyl- and thioaryl-substituted modified benzimidazoles. Antibacterial and antiprotozoal activity of the newly obtained compounds was studied. Some thioalkyl derivatives showed remarkable activity against nosocomial strains of Stenotrophomonas malthophilia, and an activity comparable to that of metronidazole against gram-positive and gram-negative bacteria. Of the tested compounds, 5,6-dichloro-2-(4-nitrobenzylthio)-benzimidazole showed the most distinct antiprotozoal activity.

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17

Sontakke, Vyankat A., Sougata Ghosh, Pravin P. Lawande, Balu A. Chopade, and Vaishali S. Shinde. "A Simple, Efficient Synthesis of 2-Aryl Benzimidazoles Using Silica Supported Periodic Acid Catalyst and Evaluation of Anticancer Activity." ISRN Organic Chemistry 2013 (April 24, 2013): 1–7. http://dx.doi.org/10.1155/2013/453682.

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A new, efficient method for the synthesis of 2-aryl substituted benzimidazole by using silica supported periodic acid (H5IO6-SiO2) as a catalyst has been developed. The salient feature of the present method includes mild reaction condition, short reaction time, high yield and easy workup procedure. The synthesized benzimidazoles exhibited potent anticancer activity against MCF7 and HL60 cell lines.

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18

Francesconi, Valeria, Elena Cichero, Silvia Schenone, Lieve Naesens, and Michele Tonelli. "Synthesis and Biological Evaluation of Novel (thio)semicarbazone-Based Benzimidazoles as Antiviral Agents against Human Respiratory Viruses." Molecules 25, no. 7 (March 25, 2020): 1487. http://dx.doi.org/10.3390/molecules25071487.

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Respiratory RNA viruses are responsible for recurrent acute respiratory illnesses that still represent a major medical need. Previously we developed a large variety of benzimidazole derivatives able to inhibit these viruses. Herein, two series of (thio)semicarbazone- and hydrazone-based benzimidazoles have been explored, by derivatizing 5-acetyl benzimidazoles previously reported by us, thereby evaluating the influence of the modification on the antiviral activity. Compounds 6, 8, 16 and 17, bearing the 5-(thio)semicarbazone and 5-hydrazone functionalities in combination with the 2-benzyl ring on the benzimidazole core structure, acted as dual inhibitors of influenza A virus and human coronavirus. For respiratory syncytial virus (RSV), activity is limited to the 5-thiosemicarbazone (25) and 5-hydrazone (22) compounds carrying the 2-[(benzotriazol-1/2-yl)methyl]benzimidazole scaffold. These molecules proved to be the most effective antiviral agents, able to reach the potency profile of the licensed drug ribavirin. The molecular docking analysis explained the SAR of these compounds around their binding mode to the target RSV F protein, revealing the key contacts for further assessment. The herein-investigated benzimidazole-based derivatives may represent valuable hit compounds, deserving subsequent structural improvements towards more efficient antiviral agents for the treatment of pathologies caused by these human respiratory viruses.

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19

Di Gioia, Maria Luisa, Roberta Cassano, Paola Costanzo, Natividad Herrera Cano, Loredana Maiuolo, Monica Nardi, Fiore Pasquale Nicoletta, Manuela Oliverio, and Antonio Procopio. "Green Synthesis of Privileged Benzimidazole Scaffolds Using Active Deep Eutectic Solvent." Molecules 24, no. 16 (August 8, 2019): 2885. http://dx.doi.org/10.3390/molecules24162885.

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The exploitation and use of alternative synthetic methods, in the face of classical procedures that do not conform to the ethics of green chemistry, represent an ever-present problem in the pharmaceutical industry. The procedures for the synthesis of benzimidazoles have become a focus in synthetic organic chemistry, as they are building blocks of strong interest for the development of compounds with pharmacological activity. Various benzimidazole derivatives exhibit important activities such as antimicrobial, antiviral, anti-inflammatory, and analgesic activities, and some of the already synthesized compounds have found very strong applications in medicine praxis. Here we report a selective and sustainable method for the synthesis of 1,2-disubstituted or 2-substituted benzimidazoles, starting from o-phenylenediamine in the presence of different aldehydes. The use of deep eutectic solvent (DES), both as reaction medium and reagent without any external solvent, provides advantages in terms of yields as well as in the work up procedure of the reaction.

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20

Dwivedi, Parmesh Kumar, and Devdutt Chaturvedi. "Synthesis and Antimicrobial Evaluations of Sulfur Inserted Fluoro-Benzimidazoles." Asian Journal of Chemistry 33, no. 7 (2021): 1525–29. http://dx.doi.org/10.14233/ajchem.2021.23174.

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A new series of fluorinated sulfur inserted benzimidazole analogues Za-i were synthesized and characterized. The new compounds were screened for their antimicrobial and antioxidant potential. The synthesized compounds were obtained by multiple step synthesis, initiating from the synthesis of 5-(difluoromethoxy)-1H-benzimidazole-2-thiol X. The compounds Ya-i prepared by reacting differently substituted anilines with chloroacetylchloride and triethylamine in DMF. Finally, the compound X was reacted with different derivatives of 2-chloro-N-phenylacetamide resulting in formation of titled compounds Za-i. The synthesized compounds (Za-Zi) were characterized by spectral analysis viz.1H & 13C NMR, mass spectra, elemental analysis and IR. The in vitro antimicrobial potential against Gram-positive (S. aureus and E. faecalis) and Gram-negative bacterial (E. coli and P.aeruginosa) strains as well as fungi (A. niger and C. albicans) was recorded for the obtained compounds. Some of the compounds exhibited encouraging results (in MIC) against Gram-positive and Gram-negative bacterial strains. These studies thus suggest that the designed sulfur inserted fluoro-benzimidazoles scaffold may serve as new promising template for further amplification as antimicrobial agents.

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21

Sapijanskaitė-Banevič, Birutė, Vykintas Palskys, Rita Vaickelionienė, Jūratė Šiugždaitė, Povilas Kavaliauskas, Birutė Grybaitė, and Vytautas Mickevičius. "Synthesis and Antibacterial Activity of New Azole, Diazole and Triazole Derivatives Based on p-Aminobenzoic Acid." Molecules 26, no. 9 (April 29, 2021): 2597. http://dx.doi.org/10.3390/molecules26092597.

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The p-aminobenzoic acid was applied for the synthesis of substituted 1-phenyl-5-oxopyrrolidine derivatives containing benzimidazole, azole, oxadiazole, triazole, dihydrazone, and dithiosemicarbazide moieties in the structure. All the obtained compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes, Salmonella enteritidis, Escherichia coli, and Pseudomonas aeruginosa by using MIC and MBC assays. This study showed a good bactericidal activity of γ-amino acid and benzimidazoles derivatives. The antimicrobial activity of the most promising compounds was higher than ampicillin. Furthermore, two benzimidazoles demonstrated good antimicrobial activity against L. monocytogenes (MIC 15.62 µg/mL) that was four times more potent than ampicillin (MIC 65 µg/mL). Further studies are needed to better understand the mechanism of the antimicrobial activity as well as to generate antimicrobial compounds based on the 1-phenyl-5-oxopyrrolidine scaffold.

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22

Gadde, Satyanarayana, Yun Cheuk Leung, Mohan Bhadbade, Belamy B. Cheung, David StC Black, and Naresh Kumar. "Synthesis of a Novel Library of 1-Substituted Pyrido[1,2-a]benzimidazoles." Australian Journal of Chemistry 73, no. 12 (2020): 1208. http://dx.doi.org/10.1071/ch20173.

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The reactivity and synthesis of new analogues of pyrido[1,2-a]benzimidazoles have been explored. Twenty-three derivatives bearing phenoxy, thiophenoxy, aniline, and aryl groups at the 1-position were successfully synthesised in 25–91% yield, via nucleophilic substitution, Buchwald–Hartwig amination, and Suzuki coupling type processes. Solvent free synthetic protocols were employed to achieve the nucleophilic substitution of anilines with electron donating groups or moderately electron withdrawing groups on a sterically demanding intermediate (7a). An unusual polycyclic heterocycle was identified as a side-product during this work: a dimeric bis(pyrido[1,2-a]benzimidazole).

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23

Kapil, Choudhary, Bhavsar Rupali, and Chaturvedi Prerna. "Synthesis and Characterization of Benzimidazole Derivatives for Antimicrobial Property." International Journal of Pharmaceutical Sciences and Medicine 6, no. 8 (August 30, 2021): 134–43. http://dx.doi.org/10.47760/ijpsm.2021.v06i08.009.

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Benzimidazoles are an important class of compounds with a wide spectrum of biological activity ranging from anti-hypertensive, anti-viral, anti-microbial, antitumor and anthelmintic activity. Benzimidazole rings are the most important nitrogen-containing heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery. Due to their special structural features and electron-rich environment, Benzimidazole containing drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of bioactivities. Numerous benzimidazole based drugs have been extensively used in the clinic to treat various types of diseases with high therapeutic potential. The main objective of present work was to study the anti-microbial activity of the Benzimidazole drivatives. A series of benzimidzole derivatives have been synthesized and identified. The compounds were synthesized by using ethyl acetate and benzene as starting material. The series of 1, 2-disubstituted benzimidazoles containing pyrimidine and other functional groups was prepared which provides advantages such as, easy workup and high yield. All reagents used for synthesis were of synthetic grade. Purification of all compounds was done by thin layer chromatography using silica gel G as absorbent on glass plate using acetate: benzene (6:4 v/v %), Toluene: Acetone (8:2 v/v %) and Ethyl Acetate: n- Hexane (6:4 v/v %) as mobile phase. Compounds were detected by using iodine vapor as detecting agent. All compounds show single spot. All the newly synthesized compounds were characterized by IR spectral study. The compounds were investigated for their antimicrobial activity against clinical standard drug Ciprofloxacin. The anti-microbial study of the synthesized derivative was done Broad panels of bacterial and fungal strains were used for testing the antimicrobial properties of the synthesized molecules III1-13. The compounds III1 (m-NO2), III2 (p-NO2), III3 (m-Cl), III4 (3-F-4-Cl) and III9 (p-OCH3) showed excellent activity (62.5 μg/ml), even better than ciprofloxacin.

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24

Kazimierczuk, Z., R. Stolarski, and D. Shugar. "Stereospecific Synthesis by the Sodium Salt Glycosylation Method of Halogeno Benzimidazole 2′ -Deoxyribose Analogues of the Inhibitor of hnRNA Synthesis, 5,6-Dichloro-1-(β-ᴅ-ribofuranosyl)benzimidazole (DRB)." Zeitschrift für Naturforschung C 40, no. 9-10 (August 1, 1985): 715–20. http://dx.doi.org/10.1515/znc-1985-9-1023.

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Abstract The recently developed stereospecific sodium salt glycosylation procedure has been successfully applied to the synthesis of the β-ᴅ-2′-deoxyribofuranosides of benzimidazole, 5,6-dihalogeno benzimidazoles, and some 2-substituted analogues in high yield. The 5,6-dibromo analogue was obtained by bromination of the parent nucleoside. These have all been characterized by spectroscopic methods, including 1H NMR, which permitted analyses of their solution conformations and comparison with those of the corresponding ribofuranosides. Some biological aspects, including preliminary results on cytotoxicity and antiviral activity, are briefly considered.

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25

El Bialy, Serry Atta, Basem Mansour, Waleed Abdelhakeem Bayoumi, Amira Taman, and Hassan Mohammed Eissa. "Novel 2-(5-Aryl)thiophen-2-yl)benzimidazoles; Design, Synthesis and In vitro Evaluation Against Cercarial Phase of Schistosoma mansoni." Letters in Drug Design & Discovery 17, no. 11 (October 23, 2020): 1432–38. http://dx.doi.org/10.2174/1570180817999200523181211.

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Background: Literature survey has pointed out that Benzimidazoles represent an interesting class of anthelmintics, of which several potent members were developed. Objective: Benzimidazoles hybridized with pharmacophoric moieties possessing anthelmintic activity were designed, synthesized to be evaluated against cercaria. Methods: Structural modification was achieved through 2- and 5-positions. Moreover, an in vitro cercarial assay was adopted to evaluate target compounds. Results and Discussion: Biological screening revealed that compound 3h showed significant activity with a survival index of 35% at a 100 μg/mL concentration. Whereas, compounds 3a and 3c showed moderate activity, the rest of the tested compounds exhibited low activity. Conclusion: The current study evidenced that the new hybrids "benzimidazole-thiophen-aryl" are successful as cercacidal agents. Further studies of this novel tri-ring system are suggested on adult worms of S. mansoni.

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26

Journal, Baghdad Science. "Synthesis of Some New Nucleoside Analogues Containing Seven Membered Ring and Studying Their Biological Activity." Baghdad Science Journal 13, no. 3 (September 4, 2016): 531–46. http://dx.doi.org/10.21123/bsj.13.3.531-546.

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In this work, a series of new Nucleoside analogues (D-galactopyranose linked to oxepanebenzimidazole moiety) was synthesized via multisteps synthesis. The first step involved preparation of two benzimidazoles 2-styrylbenzimidazole and 2-(phenyl ethynyl) benzimidazole via reaction of phenylenediamine with cinnamic acid or ?-phenyl propiolic acid. Electrophilic addition of the prepared benzimidazoles by three anhydrides in the second step afforded (4-6) and (14-16) which in turn were treated with 1,2,3,4-di-O-isopropylidene galactopyranose in the third step to afford a series of the desirable protected nucleoside analogues (7-9) ,(17-19)which after hydrolysis in methanolic sodium methoxidein the fourth step afforded the free nucleoside analogues (10-12) and (20-22) .The synthesized compounds were identified by FT-IR and some of them by 1H-NMR and13C-NMR. The synthesized oxepane nucleoside analogues were screened for their antibacterial activity against three types of bacteria including Staphylococcusaureus ,Bacillus(gram positive) andE.coli (gram negative) bacteria repectively.

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27

Al-Zaydi, Khadijah Mohamed, Mariam Abd Alha Al-Shiekh, and Ebtisam Abdel-Aziz Hafez. "Enaminonitriles in Heterocyclic Synthesis: New Routes for the Synthesis of Some Novel Azolo[1,5-a]pyrimidine, Pyrimido[1,2-a]benzimidazole, Pyrido[1,2-a]benimdazole, Pyrazolo[3,4-b]pyridine, Pyrazole and Pyrimidine Derivatives." Journal of Chemical Research 2000, no. 1 (January 2000): 13–15. http://dx.doi.org/10.3184/030823400103165716.

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28

Yang, Kang, Huiwen Gu, Fang Zhang, Xiaojuan Xu, Lijie Zhang, and Yaquan Sun. "Synthesis of 1,2,6-Trisubstituted Benzimidazoles." Chinese Journal of Organic Chemistry 38, no. 8 (2018): 2130. http://dx.doi.org/10.6023/cjoc201802027.

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29

Mayer, John P., George S. Lewis, Celesta McGee, and Danute Bankaitis-Davis. "Solid-phase synthesis of benzimidazoles." Tetrahedron Letters 39, no. 37 (September 1998): 6655–58. http://dx.doi.org/10.1016/s0040-4039(98)01427-0.

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30

Phillips, Gary B., and Guo Ping Wei. "Solid phase synthesis of benzimidazoles." Tetrahedron Letters 37, no. 28 (July 1996): 4887–90. http://dx.doi.org/10.1016/0040-4039(96)01002-7.

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31

Perkins, James J., Amy E. Zartman, and Robert S. Meissner. "Synthesis of 2-(alkylamino)benzimidazoles." Tetrahedron Letters 40, no. 6 (February 1999): 1103–6. http://dx.doi.org/10.1016/s0040-4039(98)02592-1.

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32

Yeh, Chih-Ming, and Chung-Ming Sun. "Rapid Parallel Synthesis of Benzimidazoles." Synlett 1999, no. 6 (June 1999): 810–12. http://dx.doi.org/10.1055/s-1999-2739.

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33

Montini, Tiziano, Valentina Gombac, Juan J. Delgado, Anna Maria Venezia, Gianpiero Adami, and Paolo Fornasiero. "Sustainable photocatalytic synthesis of benzimidazoles." Inorganica Chimica Acta 520 (May 2021): 120289. http://dx.doi.org/10.1016/j.ica.2021.120289.

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34

Singh, Namrata, Annamalai Pandurangan, Kavita Rana, Preeti Anand, Arsad Ahamad, and Amit Kumar Tiwari. "Benzimidazole: A short review of their antimicrobial activities." International Current Pharmaceutical Journal 1, no. 5 (April 7, 2012): 110–18. http://dx.doi.org/10.3329/icpj.v1i5.10284.

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Benzimidazole is the heterocyclic compound formed from benzene and imidazole ring containing nitrogen, oxygen sulphor and its derivatives are of wide interest because of their diverse biological activity and clinical applications, they are remarkably effective compounds both with respect to their inhibitory activity and their favourable selectivity ratio. Reported nucleus is a constituent of vitamin-B12. Benzimidazoles are regarded as a promising class of bioactive heterocyclic compounds that exhibit a range of biological activities like anti-microbial, anti-viral, anti-diabetic, anti-cancer activity, numerous anti-oxidant, anti-parasitic, anti-helmintics, anti-proliferative, anti-HIV, anti-convulsant, anti-inflammatory, anti-hypertensive, anti-neoplastic, proton pump inhibitor and anti-trichinellosis. Benzimidazoles exhibit significant activity as potential antitumor agents, smooth muscle cell proliferation inhibitors, a treatment for intestinal cystitis, and in diverse area of chemistry. Some of the important benzimidazole derivatives have been reported as thyroid receptor agonist gonadotropin releasing hormone receptor antagonists, non-nucleoside HIV-1 reverse transcriptase inhibitors and interestingly alkynylbenzimidazoles as modulators of metabotropic glutamate receptors. The imidazole core is a common moiety in a large number of natural products and pharmacologically active compounds. The synthesis of novel benzimidazole derivatives remains a main focus of medicinal research. This comprehensive overview summarizes the chemistry of different derivative of substituted benzimidazole along with their anti-microbial activity containing anti-malarial anti-fungal, anti-bacterial, anti-viral activities.DOI: http://dx.doi.org/10.3329/icpj.v1i5.10284International Current Pharmaceutical Journal 2012, 1(5): 119-127

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35

Dzvinchuk, I. B., A. V. Turov, and M. O. Lozinskii. "Synthesis of pyrido[1,2-a]benzimidazoles from 2-acylmethyl-1H-benzimidazoles." Chemistry of Heterocyclic Compounds 42, no. 7 (July 2006): 929–34. http://dx.doi.org/10.1007/s10593-006-0182-3.

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36

Sharghi, Hashem, Mona Hosseini-Sarvari, and Fatemeh Moeini. "Copper-catalyzed one-pot synthesis of benzimidazole derivatives." Canadian Journal of Chemistry 86, no. 11 (November 1, 2008): 1044–51. http://dx.doi.org/10.1139/v08-153.

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A simple, efficient, and environmentally benign method has been developed for the synthesis of 2-substituted benzimidazoles through a one-pot reaction of phenylenediamines with aryl aldehydes in excellent isolated yields under mild conditions using Cu(II) complex as the selective, recyclable, and heterogeneous catalyst at ambient temperature. The Cu(II) complex as a heterogeneous catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for eight successive runs. No metal-complex leaching was observed after the consecutive catalytic reactions. The salient features of this method include mild conditions, high yields, simple procedure, and good recovery and reusability of the heterogeneous catalyst.Key words: benzimidazole, o-phenylenediamine, arylaldehydes, heterogeneous catalyst, N,N-bis (2-hydroxyphenyl)pyridine-2,6-dicarboxamide.

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37

Kokitkar, S. V., and N. P. Shetgiri. "Synthesis, Spectral Studies and Biological Activity of 4′-Oxothiazolidinyl Benzimidazoles." Journal of Chemical Research 2000, no. 7 (July 2000): 336–38. http://dx.doi.org/10.3184/030823400103167543.

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New 2-methyl-1-[(2′-substituted phenyl-4′-oxothiazolidinyl)aminocarbonylmethyl)]-1H-benzimidazoles (3) and 2-methyl-1-[(2′-substituted phenyl-5′-methyl-4′-oxothiazolidinyl) aminocarbonylmethyl]-1H-benzimidazoles (4) are synthesized, characterized and evaluated for their antimicrobial and antitubercular activity.

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38

Kattimani, Pramod P., Ravindra R. Kamble, and Gangadhar Y. Meti. "Expedient synthesis of benzimidazoles using amides." RSC Advances 5, no. 37 (2015): 29447–55. http://dx.doi.org/10.1039/c5ra00021a.

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In the present report an efficient, rapid, facile and inexpensive route for the synthesis of benzimidazoles using 1,2-arylenediamines and amides in acidic medium under thermal/microwave conditions is developed.

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39

Ouaket, Amine, Fatiha Moughaoui, Asmae Laaraibi, Souad Hamdouch, Mohammed Berrada, and Noureddine Knouzi. "DPPH scavenging activity of some Bis-benzimidazole derivatives." Mediterranean Journal of Chemistry 8, no. 2 (April 11, 2019): 103–7. http://dx.doi.org/10.13171/mjc8219041101ao.

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As part of our research on substituted benzimidazoles, we are interested in the synthesis of new heterocyclic molecules. This new organic molecule is a subclass of quinolines with a wide variety of biological properties. In order to affect the binding of quinoline to our bis-benzimidazole derivatives, we have chosen the "azo" bond as a means of attachment. To achieve our goal, we investigated different parameters for the reactions to determine the conditions to obtain the best results. This article discusses the antioxidant activity of our molecules using the DPPH method.

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40

Elumalai, Vijayaragavan, and Jørn H. Hansen. "A Green, Scalable, One-Minute Synthesis of Benzimidazoles." Synlett 31, no. 06 (January 24, 2020): 547–52. http://dx.doi.org/10.1055/s-0039-1690797.

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Herein is reported a substantially improved synthesis of 2-substituted benzimidazoles by condensation of 1,2-diaminoarenes and aldehydes using methanol as the reaction medium. The developed method afforded moderate to excellent yields (33–96%) at ambient temperature, displays high functional group tolerance, is conducted open to air, and requires only one minute reaction time under catalyst- and additive-free conditions. Moreover, the efficient protocol permits scale-up to multi-gram scale synthesis of benzimidazoles and will become a method of choice when constructing such heterocyclic systems.

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41

Babbar, Ritchu, Swikriti, and Sandeep Arora. "A Comprehensive Review on Therapeutic Potential of Benzimidazole: A Miracle Scaffold." Journal of Pharmaceutical Technology, Research and Management 8, no. 1 (May 20, 2020): 23–29. http://dx.doi.org/10.15415/jptrm.2020.81004.

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Background: Benzimidazole is a category of heterocyclic aromatic compounds formed from the fusion of six membered benzene with five membered imidazolering. The moiety possesses diverse biological and clinical applications. A number of studies have shown that a varied substituent around the benzimidazole nucleus results in pharmacologically active compounds of therapeutic interest. Purpose: Owing to its number of pharmacological properties, this moiety is of choice of interest in designing and synthesis of new therapeutic compounds. The existence of the benzimidazole core in numerous groups of biological agents like antimicrobial, antiviral, antiparasitic, antihypertensive, anticancer, CNS stimulant as well as depressants has made important scaffold for development of many newer therapeutic agents. There is utmost need to understand the synthesis and associated role of benzimidazole derived compounds in different diseases. Therefore, in the present review, we attempt to discuss various derivatives of benzimidazole nucleus with different pharmacological activities. Conclusion: Benzimidazoles have played a great role in discovery of drug and development. Huge attempt has been made towards benzimidazole heterocyclic-based organic compounds with great excellence that resulted in drugs with enormous biological activity. Therapeutic drugs containing benzimidazole nucleus are used in building drugs that serve to be an active area of research. This article becomes a source that will lead to discovery of new opportunities for all researchers interested in benzimidazole-based heterocyclic medicinal chemistry.

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42

Poor Heravi, Mohammad Reza, and Marjan Ashori. "Boric Acid Catalyzed Convenient Synthesis of Benzimidazoles in Aqueous Media." Journal of Chemistry 2013 (2013): 1–5. http://dx.doi.org/10.1155/2013/496413.

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Synthesis of benzimidazoles has been developed by theo-phenylenediamine with aldehydes using boric acid an efficient catalyst under mild reaction conditions in aqueous media. The product is applicable to aryl and heteroaryl aldehydes. This reaction led to the formation of benzimidazoles new derivatives in good yields. The FT-IR,19F-NMR,1H-NMR,13C-NMR spectra and elemental analysis confirm the structure of compounds.

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43

Dzvinchuk, I. B., and M. O. Lozinskii. "Synthesis of 2-(3-Indolyl)-1H-benzimidazoles from 2-Acylmethyl-1H-benzimidazoles." Chemistry of Heterocyclic Compounds 41, no. 2 (February 2005): 177–80. http://dx.doi.org/10.1007/s10593-005-0123-6.

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44

Dzvinchuk, I. B., and M. O. Lozinskii. "Synthesis of 2-(3-furyl)-1H-benzimidazoles from 2-phenacyl-1H-benzimidazoles." Chemistry of Heterocyclic Compounds 43, no. 11 (November 2007): 1390–96. http://dx.doi.org/10.1007/s10593-007-0215-6.

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45

Vanelle, Patrice, Yves Njoya, Narimène Boufatah, Armand Gellis, Pascal Rathelot, Michel P. Crozet, and Patrice Vanelle. "Microwave Assisted Synthesis of New Benzimidazoles." HETEROCYCLES 57, no. 8 (2002): 1423. http://dx.doi.org/10.3987/com-02-9500.

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46

Tumelty, David, Matthias K. Schwarz, Kathy Cao, and Michael C. Needels. "Solid-phase synthesis of substituted benzimidazoles." Tetrahedron Letters 40, no. 34 (August 1999): 6185–88. http://dx.doi.org/10.1016/s0040-4039(99)01299-x.

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47

Shen, Wang, Todd Kohn, Zice Fu, XianYun Jiao, Sujen Lai, and Michael Schmitt. "Synthesis of benzimidazoles from 1,1-dibromoethenes." Tetrahedron Letters 49, no. 51 (December 2008): 7284–86. http://dx.doi.org/10.1016/j.tetlet.2008.10.030.

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48

Kurhade, Santosh, Arianna Rossetti, and Alexander Dömling. "Facile Synthesis of N-Substituted Benzimidazoles." Synthesis 48, no. 21 (June 23, 2016): 3713–18. http://dx.doi.org/10.1055/s-0035-1562436.

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49

Penieres, C. Guillermo, A. Bonifas Imelda, C. López Jose Guadalupe, E. García Guadalupe José, and T. Cecilio Alvarez. "Synthesis of Benzimidazoles in Dry Medium." Synthetic Communications 30, no. 12 (January 2000): 2191–95. http://dx.doi.org/10.1080/00397910008087397.

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50

Park, Sehyun, Jaehun Jung, and Eun Jin Cho. "Visible-Light-Promoted Synthesis of Benzimidazoles." European Journal of Organic Chemistry 2014, no. 19 (May 22, 2014): 4148–54. http://dx.doi.org/10.1002/ejoc.201402141.

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