Benzimidazole: Chemical property, Primary Use, and biological activity

Introduction

Benzimidazole is a white solid, aromatic heterocyclic organic compound. It is formed by fusing the aromatic benzene ring with the heterocyclic imidazole aromatic ring. It is also called 1H-1,3-benzimidazole and 1H-benzo[d]imidazole and it has the general formula C7H6N2. The benzimidazole compound has aroused researchers' interest over the past decades in research and application because of the distinctive properties of the organic compounds derived from it and because of its well-known biological applications and many important medicinal properties.

Chemical property

Benzimidazole is a class of heterocyclic aromatic organic compounds which share a fundamental structural characteristic of six-membered benzene fused to the 4 and 5-position of the five-membered imidazole ring system. The hydrogen atom attached to nitrogen in the 1-position of the benzimidazole nucleus readily tautomerizes, which is responsible for isomerization in the derived compounds. The NH group present in benzimidazole is relatively strongly acidic and also weakly basic in nature. Benzimidazole is an amphoteric compound with an ionization constant (pKa) value for benzimidazole, and its conjugate acid is 12.8 and 5.6, respectively.

Primary Use

This benzimidazole drug is used to treat enterobiasis, strongyloidiasis, ascariasis, uncinariasis, trichuriasis, and cutaneous larva migrans. It has been advocated as an antimycotic in corneal ulcers.

The biological activity of Benzimidazole derivative

Benzimidazole has many important biological activities such as antihistamine, antifungal, antimicrobial, antiviral, anti-inflammatory, antioxidant, anti ulcerative and anticancer action, as well as others; for this reason, there is great growth and wide development of the field by researchers wanting to prepare benzimidazole derivatives. It has been reported that many molecules containing benzimidazole moiety have significant anti-inflammatory and analgesic activity. Scientists worldwide have reported remarkable activity against fungi and bacteria. In addition, the benzimidazole-substituted compounds have antiviral, anthelmintic, antiproliferative, anti-hypertensive, H3 antagonistic, human glucagon receptor antagonistic], male contraceptive and anti-infective activities. These molecules also inhibit chemokine receptor (CXCR3), interleukin 2-inducible T cell kinase (ITK) and lymphocyte tyrosine kinase (Lck). 1-H Benzimidazole and its simple derivatives have also been claimed to prevent stomach damage caused by inflammation inhibitors. N-containing benzimidazole derivatives have well-known biological activities such as proton pump inhibitor (Omeprazole), antihelminthic (Albendazole), antidopaminergic (Domperidone) and antipsychotic (Pimozide).

References

[1]Chung, Nguyen Thi Vo Cong Dung and Dau Xuan Duc. "Recent achievements in the synthesis of benzimidazole derivatives.” RSC Advances 46 (2023):32734-32771.

[2] Lee, Yeuan Ting et al. “Benzimidazole and its derivatives as cancer therapeutics: The potential role from traditional to precision medicine.” Acta pharmaceutica Sinica. B vol. 13,2 (2023): 478-497. doi:10.1016/j.apsb.2022.09.010

[3] Benzimidazole - an overview | ScienceDirect Topics https://www.sciencedirect.com/topics/chemistry/benzimidazole