Synthesis, characterisation, biological and theoretical studies of novel pyridine derivatives

Diversely functionalised pyrazolone analogues have been reported to display a wide range of biological activities. In this paper, we report the synthesis of a series of novel analogues based on piperidine fused pyrazolone core and explore its potential as novel antibacterial agents. The synthesised...

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Bibliographic Details
Published in:	Molecular physics Vol. 120; no. 13
Main Authors:	Pradeep Kumar, P. S., Sunil, K., Chethan, B. S., Lokanath, N. K., Madan, N., Sajith, A. M.
Format:	Journal Article
Language:	English
Published:	Abingdon Taylor & Francis 03-07-2022 Taylor & Francis Ltd
Subjects:	Bacteria Bicyclisation biological activity Chemical properties Chemical synthesis Density functional theory DFT E coli Hydrazines NBO NMR Nuclear magnetic resonance Piperidine Pyrazole Pyrazolones Quantum chemistry Scaffolds
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Summary:	Diversely functionalised pyrazolone analogues have been reported to display a wide range of biological activities. In this paper, we report the synthesis of a series of novel analogues based on piperidine fused pyrazolone core and explore its potential as novel antibacterial agents. The synthesised compounds were analysed using spectroscopic techniques such as 1 H NMR, LC-MS, and FT-IR. The major highlight involves the cyclisation reaction of tert-butyl-4-methyl 3-oxopiperidine-1,4-dicarboxylate with the hydrazine component to access the privileged piperdine fused pyrazolone scaffold. This scaffold was further treated with HCl to remove the amine protecting group and subsequently reacted with acid chlorides to deliver the final products in excellent yields. Density functional theory (DFT) calculations were performed to determine the various molecular properties of the synthesised compounds. Based on the reactive sites explored by the molecular electrostatic potential maps, the compounds were screened against two gram positive bacterial strains namely S. aureus, and M. luteus, and a gram negative bacterial strain namely E.coli. Highlights A Series of novel pyrazole derivatives were synthesised using bicyclisation strategy. Computational methods were used to determine various quantum chemical properties. All molecules were screened against S. aureus, M. luteus, and E. coli bacterial strains.
ISSN:	0026-8976 1362-3028
DOI:	10.1080/00268976.2022.2093283