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

Harini, Salakatte Thammaiah and Kumar, Honnaiah Vijay and Peethambar, Sannenahalli Krishnegowda and Rangaswamy, Javarappa and Naik, Nagaraja (2014) Novel 2,6-bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters: synthesis and a new insight into their antioxidant and antimicrobial potential. In: MEDICINAL CHEMISTRY RESEARCH, 23 (4). pp. 1887-1898.

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Official URL: http://dx.doi.org/10.1007/s00044-013-0793-z

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 oximation with hydroxylamine hydrochloride (NH(2)OHa (TM) 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, H-1 NMR, C-13 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: Journal Article
Additional Information: Copyright for this article belongs to the SPRINGER BIRKHAUSER, USA
Keywords: 2,6-Bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters; Substituted benzoyl chlorides; Antioxidant; Antimicrobial studies
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 14 Mar 2014 10:17
Last Modified: 14 Mar 2014 10:17
URI: http://eprints.iisc.ac.in/id/eprint/48619

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