Novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters: Synthesis and a new insight into their antioxidant and antimicrobial potential

Harini, S. T. and Vijay Kumar, H. and Peethambar, S. K. and Rangaswamy, J. and Naik, N. (2014) Novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters: Synthesis and a new insight into their antioxidant and antimicrobial potential. Medicinal Chemistry Research, 23. pp. 1887-1898. ISSN 1554-8120

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Abstract

A simple and efficient protocol for the synthesis of novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters 4(a-q) is described. Initially, p-anisaldehyde 1 was condensed (Mannich reaction) with acetone and ammonium acetate trihydrate afforded 2,6-bis(4-methoxyphenyl) piperidin-4-one 2. Then, methylation followed by oximationwith hydroxylamine hydrochloride (NH2OH�HCl) furnished a key scaffold 4. Further, to explore the enhanced biological properties of the piperidin-4-one core i.e. the key scaffold 4 was conjugated with substituted benzoyl chlorides in the presence of anhydrous K2CO3 as base to obtain novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters 4(a-q) in excellent yields. The newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and mass spectroscopic techniques, and screened for their in vitro antioxidant and antimicrobial activities. Most of the compounds exerted positive efficacy towards the biological assays performed. Among the synthesized analogues, compounds 4l and 4m exhibited promising antioxidant activity and on the other hand compounds 4b and 4d manifested persuasive antibacterial activity, whereas compound 4b displayed stupendous antifungal activity against A. flavus strain.

Item Type:	Article
Uncontrolled Keywords:	4, carbon nuclear magnetic resonance, controlled study, drug synthesis, in vitro study, nonhuman, proton nuclear magnetic resonance, unclassified drug, antibacterial activity, antifungal activity, antifungal agent, antiinfective agent, Candida albicans, Escherichia coli, Staphylococcus aureus, antioxidant, antioxidant activity, drug efficacy, article, 2, Pseudomonas aeruginosa, fluconazole, streptomycin, Aspergillus flavus, IC 50, ester derivative, methylation, butylated hydroxyanisole, oxime derivative, 2 2, 4 dimethoxybenzoyl oxime, 4 dinitrobenzoyl oxime, 5 dihydroxybenzoyl oxime, 5 trihydroxybenzoyl oxime, 5 trimethoxybenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 2, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 2 hydroxybenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 3, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 3 chlorobenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 3 hydroxybenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 bromobenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 chlorobenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 fluorobenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 hydroxybenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 methoxybenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 methylbenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o 4 nitrobenzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one o benzoyl oxime, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 one oxime ester derivative, 6 bis(4 methoxyphenyl) 1 methylpiperidin 4 ylideneaminooxy]carbonyl]phenyl acetate, Chrysosporium keratinophilum
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	20 Jun 2019 10:07
Last Modified:	10 Jul 2019 05:33
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3512

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