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Molecular docking, synthesis, and antimycobacterial activities of pyrrolyl hydrazones and their copper complexes

Authors Joshi S, Dixit S, Gadag S, Kulkarni V, Aminabhavi T

Received 3 July 2015

Accepted for publication 23 October 2015

Published 30 December 2015 Volume 2016:6 Pages 1—14

DOI https://doi.org/10.2147/RRMC.S90564

Checked for plagiarism Yes

Review by Single-blind

Peer reviewer comments 3

Editor who approved publication: Dr Xing-Cong Li


Shrinivas D Joshi, Sheshagiri R Dixit, Shivprasad Gadag, Venkatrao H Kulkarni, Tejraj M Aminabhavi

Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, SET’s College of Pharmacy, Dharwad, Karnataka, India


Abstract: A novel series of pyrrole derivatives were designed and synthesized with an aim to overcome the growing antitubercular resistance and develop more potent antimicrobial agents. In this pursuit, a novel series of 4-(1H-pyrrol-1-yl)benzoic acid hydrazide Schiff bases were synthesized and reacted with copper acetate to form the respective copper complexes. The reaction of ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate/ethyl-4-(1H-pyrrol-1-yl)benzoate with hydrazine hydrate produced ethyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazide/ethyl 4-(1H-pyrrol-1-yl)benzohydrazide. The reaction of these hydrazides with different aldehydes yielded N’-(arylidene)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzohydrazides/N’-(arylidene)-4-(1H-pyrrol-1-yl)benzohydrazides. Furthermore, these Schiff bases were reacted with copper acetate to produce respective copper complexes. All the synthesized compounds were screened for antitubercular activity using microplate alamar blue assay method that showed reasonably good minimum inhibitory concentration (MIC) values ranging from 3.12 to 50 µg/mL compared to the standard drugs like pyrazinamide (MIC =3.125 µg/mL) and streptomycin (MIC =6.25 µg/mL). The selected compounds were evaluated for antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, and Escherichia coli using the broth microdilution assay method. It was found that these compounds exhibited good antibacterial activities in the MIC range of 3.125 to >100 µg/mL when compared against standard drugs like ciprofloxacin and norfloxacin.

Keywords: synthesis, Surflex-Dock, copper complexes, antimicrobial activities

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