One-pot synthesis of novel benzimidazoles with a naphthalene moiety as antimicrobial agents and molecular docking studies

In an attempt to design a greener approach for the synthesis of a potent class of antimicrobials, 1,2-phenylenediamine derivatives were reacted with various 1/2-carboxylic acid-substituted naphthalene derivatives to generate a series of naphthyl-substituted benzimidazole derivatives (11-19) using polyphosphoric acid as catalyst under microwave irradiation and conventional synthesis method. This is an eco-friendly and swift reaction method for a synthetic approach to diverse benzimidazoles. Structures of the synthesized compounds were established on the basis of spectral data and they were screened for their antimicrobial activity. Compound18showed maximum potency against all Gram-positive and Gram-negative bacterial strains with a minimum inhibitory concentration (MIC) value in the range of 7.81-62.50 mu g/ml. Only compound17was found to be the most active against all fungal strains with a MIC value of 15.62 mu g/ml. In this study, we performed molecular docking experiments to understand the interactions between compounds17and18andE. colitopoisomerase I, and we compared the results obtained with that of 2-(3,4-dimethoxyphenyl)-5-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-benzimidazole (DMA). Compounds17and18demonstrated strong interactions with important active site residues, similar to DMA. As a result, the compounds obtained from this study can be used in designing new potent inhibitors ofE. colitopoisomerase I.

Dergi

JOURNAL OF THE CHINESE CHEMICAL SOCIETY

Yıl

2021

Cilt

68

Sayı

2

Sayfa

374-383

ISSN

0009-4536

eISSN

2192-6549

DOI

10.1002/jccs.202000125

WoS UID

WOS:000569899500001