Investigating the Antimicrobial Activity of Derivatives of Benzotriazole

Niranjan Sanjay Chaudhari; Mohammad Safwan Akbar Ali Khan; Mohammed Fahim Abdul Azim Khan; Shaikh Mohd Owais Mohd Azam; S P Srinivas Nayak

doi:10.55544/jrasb.3.6.1

Authors

Niranjan Sanjay Chaudhari Pharm D Intern, Department of Pharmacy Practice, Parul Institute of Pharmacy & Research, Parul University, Vadodara, Gujarat, INDIA. https://orcid.org/0009-0002-3292-6177
Mohammad Safwan Akbar Ali Khan Pharm D Intern, Department of Pharmacy Practice, Parul Institute of Pharmacy & Research, Parul University, Vadodara, Gujarat, INDIA.
Mohammed Fahim Abdul Azim Khan Pharm D Intern, Department of Pharmacy Practice, Parul Institute of Pharmacy & Research, Parul University, Vadodara, Gujarat, INDIA.
Shaikh Mohd Owais Mohd Azam Pharm D Intern, Department of Pharmacy Practice, Parul Institute of Pharmacy & Research, Parul University, Vadodara, Gujarat, INDIA.
S P Srinivas Nayak Assistant Professor, Department of Pharmacy Practice, Parul Institute of Pharmacy & Research, Parul University, Vadodara, Gujarat, INDIA.

DOI:

https://doi.org/10.55544/jrasb.3.6.1

Keywords:

Benzotriazole, Antimicrobial, Benzene

Abstract

Benzotriazole derivatives have emerged as a promising class of compounds with significant antimicrobial activity. This review article delves into the diverse antimicrobial properties of benzotriazole derivatives, focusing on their efficacy against various pathogenic microorganisms. We provide a detailed examination of the chemical structure-activity relationship (SAR) of these derivatives, highlighting how modifications to the benzotriazole core influence their antimicrobial potency. The review synthesizes findings from recent studies that explore the mechanisms of action, spectrum of activity, and potential applications of benzotriazole derivatives in combating bacterial, fungal, and viral infections. Additionally, we discuss the challenges and future directions in optimizing these compounds for clinical use, including issues related to toxicity, stability, and formulation. By consolidating current research and identifying key trends, this article aims to offer a comprehensive resource for researchers and pharmaceutical developers interested in harnessing the antimicrobial potential of benzotriazole derivatives.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

References

Briguglio I, Piras S, Corona P, Gavini E, Nieddu M, Boatto G, Carta A. Benzotriazole: An overview on its versatile biological behavior. Eur J Med Chem. 2015 Jun 5;97:612-48. doi: 10.1016/j.ejmech.2014.09.089. Epub 2014 Sep 30.

Wan J, Lv PC, Tian NN, Zhu HL. Facile synthesis of novel benzotriazole derivatives and their antibacterial activities. J Chem Sci (Bangalore). 2010;122(4):597-606. doi: 10.1007/s12039-010-0094-8. Epub 2011 Jul 16.

Zhou CH, Wang Y. Recent researches in triazole compounds as medicinal drugs. S Curr Med Chem 2012; 19: 239-280.

Wei JJ, Wang Y, Wang XL, Zhou CH, Ji QG. Recent developments of 2,3-triazoles in medicinal chemistry. Chin Pharm J 2011; 46: 481-485.

Pasqualotto AC, Thiele KO, Goldani LZ. Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Curr Opin Investig Drugs 2010; 11: 165-174.

Zhang L, Peng XM, Damu GL, Geng RX, Zhou CH. Comprehensive review in current developments of imidazole-based medicinal chemistry. Med Res Rev 2014; 34: 340-437.

Cui SF, Wang Y, Lv JS, Damu GLV, Zhou CH. Recent advances in application researches of thiazole compounds. Scientia Sinica Chimica 2012; 42: 1105- 1131.

Zhang FF, Gan LL, Zhou CH. Synthesis, antibacterial and antifungal activities of some carbazole derivatives. Bioorg Med Chem Lett 2010; 20: 1881- 1884.

Bajaj, K.; Sakhuja, R. Benzotriazole: Much More Than Just Synthetic Heterocyclic Chemistry. In The Chemistry of Benzotriazole Derivatives; Springer, 2015, pp 235−283

PubChem [Internet]. Bethesda (MD): National Library of Medicine (US), National Center for Biotechnology Information; 2004-. PubChem Compound Summary for CID 7220, 1H-Benzotriazole; [cited 2024 Aug. 25]. Available from: https://pubchem.ncbi.nlm.nih.gov/compound/1H-Benzotriazole

Gangurde KB, More RA, Adole VA, Ghotekar DS. Design, synthesis and biological evaluation of new series of benzotriazole-pyrazole clubbed thiazole hybrids as bioactive heterocycles: Antibacterial, antifungal, antioxidant, cytotoxicity study. Journal of Molecular Structure 2024;1299:136760.

Aggarwal, Nishu, and Navneet Singh. "Manifestation of antimicrobial activities: Benzotriazole." AIP Conference Proceedings. Vol. 2800. No. 1. AIP Publishing, 2023.

Singh N, Abrol V, Parihar S, Kumar S, Khanum G, Mir JM, Dar AA, Jaglan S, Sillanpää M, Al-Farraj S. Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines. ACS Omega. 2023 Oct 27;8(44):41960-41968. doi: 10.1021/acsomega.3c07315.

Ahmed Atto AL-SHUAEEB R. Synthesis of new coumarin derivatives containing aminobenzotriazole, triazole moieties and their antimicrobial activities. KJMS [Internet]. 2023 Apr. 1 [cited 2024 Aug. 25];1(1):47-5. Available from: https://www.isnra.net/index.php/kjms/article/view/861

Aziz Ibrahim D, Dalaf Khalaf S, Abd Al-Salam Ahmed N, Hussein Dalaf A. Synthesis, characterization and biological evaluation (antifungal and antibacterial) of new derivatives of indole, benzotriazole and thioacetyl chloride. Materials Today: Proceedings 2021;47:6201–10.

A. vahad Datta, Asnani Alpana, mohurl Shrikant, Kumar Praitysh, Bais Abhinav and Tale Ruchita, “Review on Synthetic Study of Benzotriazole” GSC Biological and Pharmaceutical sciences[2020] Page No-205- 225

Namdeo KP, Singh VK and Prajapati SK, “Synthesis of some 2-(substituted)-5-[(Nbenzotriazolomethyl)-1,3,4-thiadiazolyl]-4- thiazolidinones for their antifungal activity”. Indian J. Pharma. Educ. Res, (2009), 43(3), 266-271.

Aiyalu Rajasekaran, Kalasalingam Ananda Rajagopal, “ Synthesis of some novel triazole derivatives as anti-nociceptive and antiinflammatory agents” . Acta Pharm. 59 (2009) 355–364.

Sease C. Benzotriazole: a review for conservators. Studies in Conservation. Catherine Sease. 1978;23(1):76–85.

Morsy MA, Ali EM, Kandeel M, Venugopala KN, Nair AB, Greish K, et al. Screening and molecular docking of novel benzothiazole derivatives as potential antimicrobial agents. Antibiotics. 2020;9:1–15. doi: 10.3390/antibiotics9050221.

Skok Z, Barančoková M, Benek O, Cruz CD, Tammela P, Tomašič T, et al. Exploring the chemical space of benzothiazole-based DNA Gyrase B inhibitors. ACS Med Chem Lett. 2020;11:2433–40. doi: 10.1021/acsmedchemlett.0c00416.

Axford LC, Agarwal PK, Anderson KH, Andrau LN, Atherall J, Barker S, et al. Design, synthesis and biological evaluation of α-substituted isonipecotic acid benzothiazole analogues as potent bacterial type II topoisomerase inhibitors. Bioorg Med Chem Lett. 2013;23:6598–603. doi: 10.1016/j.bmcl.2013.10.058.

Maliyappa MR, Keshavayya J, Nazrulla MA, Sudhanva MS, Rangappa S. Six-substituted benzothiazole based dispersed azo dyes having antipyrine moiety: synthesis, characterization, DFT, antimicrobial, anticancer and molecular docking studies. J Iran Chem Soc. 2022;1–21. 10.1007/s13738-022-02569-w.