Design, synthesis, anti-HIV and antimicrobial study of some 3-(1H-benzo[d][1,2,3]triazol-1-yl)-N-phenylalkylamide derivatives

Objective

In the present study, a series of twenty benzotriazolyl-N-phenylalkylamide derivatives (7a-7j) and (8a-8j) were synthesized, characterized by physicochemical and spectral data (IR, ¹H NMR, ¹³C NMR and mass spectroscopy) and evaluated for their anti-HIV activity with the aim to develop novel substituted benzotriazole derivatives with broad-spectrum chemotherapeutic properties. The synthesized compound have been further evaluated as antibacterial and antifungal activity.

Method

A series of twenty benzotriazolyl-N-phenylalkylamide derivatives were synthesized by reacting substituted anilines (1) with 2-chloroacetyl chloride (2) and 3-chloropropionyl chloride (3) to form intermediate (4a-4j) and (5a-5j). Intermediates further reacted with benzotraizole (6) to form benzotriazolyl-N-alkylamide derivatives (7a-7j) and (8a-8j). The synthesized test compounds (7a-7j) and (8a-8j) were assessed by MTT colorimetric assay on C8166 cells and screened for antibacterial activity against Gram-positive bacteria: Staphylococcus aureus (NCIM 2122), Bacillus subtilis (MTCC 121) and Gram-negative bacteria: Escherichia coli (MTCC118), Pseudomonas aeruginosa (MTCC 647), Salmonella typhi (NCIM 2501), Klebsiella pneumonia (MTCC 3384) and in vitro antifungal activity against Candida albicans (MTCC 227) and Aspergillus niger (NCIM 1056) by two fold broth serial dilution method.

Result- Compounds 7h, 7j, 8i and 8j being the most active showed therapeutic index that were >24.4, 31.1, 30.5 and 51.5 compared to Zidovudine (AZT) having therapeutic index (TI) 514342.6. The test compounds 7h, 7i, 7j, 8h, 8i and 8j exhibited very high activity against all the strains of Gram (+) ve and Gram (-) ve bacteria and antifungal strains.