A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines

Степанов, А. И.; Astrat'ev, A. A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Палысаева, Надежда В.; Tyurin, A. Yu.; Aleksandrova, N. S.; Sadchikova, N. P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, L. D.; Semenov, Roman V.; Фирганг, С. И.; Kiselyov, Alex S.; Semenova, Marina N.; Семенов, В. В.

doi:10.1016/j.ejmech.2015.02.051

Cited by 27 publications

(12 citation statements)

References 38 publications

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“…Using these conditions, various electron-donor and electronwithdrawing group substituted benzimidazole derivatives 27 were obtained in moderate to good yields by the reaction of hydroximoyl chloride 26 with substituted 1,2-DABs 1 (Scheme 6). 42 Condensation of 26 with 3-methyl-1b (R 2 = H) and 3,4-dimethyl-substituted 1c (R 2 = H) 1,2-DABs gave a mixture of two isomers that differed in the position of the proton at the nitrogen in the imidazole ring. 42…”

Section: Review Synthesismentioning

confidence: 99%

Recent Developments Towards Synthesis of (Het)arylbenzimidazoles

Мамедов¹,

Zhukova²

2021

Synthesis

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Benzimidazole is an important heterocycle that is widely researched and utilized by the pharmaceutical industry and is one of the five most commonly used five-membered aromatic heterocyclic compounds approved by the US Food and Drug Administration. In view of their wide-ranging bioactivities, systems containing benzimidazole as one of the moieties occupy a special place among other benzimidazole derivatives. Since 2010, many improved synthetic strategies have been developed for the construction of hetaryl- and arylbenzimidazole molecular scaffolds under environmentally benign conditions. This review emphasizes the recent trends and modifications frequently used in the synthesis of derivatives of benzimidazole such as the Phillips–Ladenburg and Weidenhagen reactions, as well as entirely new methods of synthesis, involving oxidative cyclization, cross-coupling, ring distortion strategy, and rearrangements carried out under environmentally benign conditions.1 Introduction2 From 1,2-Diaminobenzenes with Various One-Carbon Unit Suppliers2.1 Phillips–Ladenburg Reaction2.1.1 With (Het)arenecarboxylic Acids2.2.2 With (Het)arenecarboxylic Acid Derivatives2.2 Weidenhagen Reaction2.2.1 With (Het)arenecarbaldehydes or (Het)aryl Methyl Ketones2.2.2 With Primary Alcohols2.2.3 With Primary Alkylamines2.2.4 With 2-Methylazaarenes2.2.5 With Other One-Carbon Fragment Suppliers3 From 2-Haloacetanilides and Amines4 From Amidines5 From Tetrahydroquinazolines6 Mamedov Rearrangement7 Conclusions and Outlook

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Section: Review Synthesismentioning

confidence: 99%

Recent Developments Towards Synthesis of (Het)arylbenzimidazoles

Мамедов¹,

Zhukova²

2021

Synthesis

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“…Recently, Stepanov et al reported a series of benzoimidazolyl furazanamines and evaluated their microtubule destabilizing properties in the sea urchin embryo model and in cultured human cancer cell lines. 150 Some imidazoles were studied in vitro using a tubulin polymerization assay and cell cycle distribution analysis. Further, these compounds were screened against a panel of human cancer cell lines to assess their cytotoxicities.…”

Section: Imidazoles As Microtubule Destabilizing Anticancer Agentsmentioning

confidence: 99%

Imidazoles as potential anticancer agents

2017

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Cancer is a black spot on the face of humanity in this era of science and technology. Presently, several classes of anticancer drugs are available in the market, but issues such as toxicity, low efficacy and solubility have decreased the overall therapeutic indices. Thus, the search for new promising anticancer agents continues, and the battle against cancer is far from over. Imidazole is an aromatic diazole and alkaloid with anticancer properties. There is considerable interest among scientists in developing imidazoles as safe alternatives to anticancer chemotherapy. The present article describes the structural, chemical, and biological features of imidazoles. Several classes of imidazoles as anticancer agents based on their mode of action have been critically discussed. A careful observation has been made into pharmacologically active imidazoles with better or equal therapeutic effects compared to well-known imidazole-based anticancer drugs, which are available on the market. A brief discussion of the toxicities of imidazoles has been made. Finally, the current challenges and future perspectives of imidazole based anticancer drug development are conferred.

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“…Kamal et al synthesised new benzimidazole‐linked pyrrolobenzodiazepine conjugates (Schemes ) among which compound 341c showed promising in vitro cytotoxicity against a number of human cancer cell lines. Stepanov et al synthesised a series of 4(1 H ‐benzo[d]imidazole‐2‐yl]‐furazan‐3‐amines (BIFAs) (Schemes and ) and evaluated for their anti‐proliferative effects in sea urchin embryo model and in cultured human cancer cell lines. Compound 406 was found to be the most active molecule (GI 50 = 0.24 μM) in reference to colchicine and vinblastine sulphate as reference drugs.…”

Section: Pharmacological and Synthetic Profiles Of Benzimidazole Derimentioning

confidence: 99%

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

Shrivastava

Naim

Alam

et al. 2017

Archiv der Pharmazie

129

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Cancer, also known as malignant neoplasm, is a dreadful disease which involves abnormal cell growth having the potential to invade or spread to other parts of the body. Benzimidazole is an organic compound that is heterocyclic and aromatic in nature. It is a bicyclic compound formed by the fusion of the benzene and imidazole ring systems. It is an important pharmacophore and a privileged structure in medicinal chemistry. According to the World Health Organisation (2015 survey), one in six deaths is due to cancer around the globe, accounting for 8.8 million deaths of which 70% of the cases were from low- and middle-income countries. In the efforts to develop suitable anticancer drugs, medicinal chemists have focussed on benzimidazole derivatives. This review article covers the current development of benzimidazole-based anticancer agents along with the synthetic approaches and structure-activity relationships (SAR).

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A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines

Cited by 27 publications

References 38 publications

Recent Developments Towards Synthesis of (Het)arylbenzimidazoles

Recent Developments Towards Synthesis of (Het)arylbenzimidazoles

Imidazoles as potential anticancer agents

Benzimidazole Scaffold as Anticancer Agent: Synthetic Approaches and Structure–Activity Relationship

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