Synthesis, biological valuation, and QSAR studies of novel pyrazole bearing pyridyl oxadiazole analogues as potential antimicrobial agents

TitleSynthesis, biological valuation, and QSAR studies of novel pyrazole bearing pyridyl oxadiazole analogues as potential antimicrobial agents
Publication TypeJournal Article
Year of Publication2016
AuthorsDesai, NC, Kotadiya, GM, Trivedi, AR, Khedkar, VM, Jha, PC
JournalMedicinal Chemistry Research
Volume25
Issue4
Pagination712-727
Date PublishedAPR
ISSN1054-2523
Keywords1, 3, 4-Oxadiazole, Antimicrobial activity, Cytotoxicity, Pyrazole, Pyridine, QSAR
Abstract

A new series of 1-(2-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-(pyridin-4-yl)-1,3,4 -oxadiazol-3(2H)-yl)-3-(aryl)prop-2-en-1-ones (5a-l) were synthesized by a simple and efficient synthetic protocol. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR and Mass spectroscopy. The resulting structural diversity was screened for its antimicrobial activity the following bacterial and fungal strains: two Gram-positive bacteria [Staphylococcus aureus (MTCC-96), Streptococcus pyogenes (MTCC-442)], two Gram-negative bacteria [Escherichia coli (MTCC-443), Pseudomonas aeruginosa (MTCC-1688)] and three fungal species (C. albicans, A. niger and A. clavatus). Following this, in vitro cytotoxicity activity against HeLa cell lines was measured by MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide] assay. The observations derived from the diverse assays were utilized for building classification models based on a binary QSAR approach termed recursive partitioning (RP) analysis to probe the physic-chemical properties influencing the SAR for molecules. The decision tree derived from RP analysis could highlight structural characteristics that discriminate the actives from inactives which can serve as guide to design molecules with improved potency. In silico ADME predictions were performed to gauge their pharmacokinetic, safety and drug likeness profile.

DOI10.1007/s00044-016-1511-4
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

1.436

Divison category: 
Organic Chemistry