Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core

Harini, S. T. and Vijay Kumar, H. and Rangaswamy, Javarappa and Naik, Nagaraja (2012) Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core. Bioorganic & Medicinal Chemistry Letters, 22 (24). 7588 - 7592. ISSN 1464-3405

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Abstract

The study has been achieved the efficient synthesis of vanillin derived piperidin-4-one oxime esters (5a–m) via four step reaction involved Mannich reaction of vanillin, acetone and ammonium acetate to obtain 2,6-bis(4-hydroxy-3-methoxyphenyl)-piperidin-4-one 2 followed by N-methylation and oximation. Further, to enhance the biological activity of vanillin derived piperidin-4-one oxime core, esterification of 4 with substituted benzoyl chlorides in the presence of strong organic base t-BuOK accomplished a series of vanillin derived piperidin-4-one oxime esters (5a–m). The synthesized analogues are screened for their antioxidant and antimicrobial studies and the preponderant effect of the phenyl ester substituents on the biological activity of piperidin-4-one oxime core was demonstrated. Among the tested compounds, 5i and 5j are emerged as outperformed antioxidants than standard Butylated hydroxy anisole (BHA) whereas, compounds 5b and 5d manifested potent antibacterial and antifungal activity than standard streptomycin and fluconazole respectively.

Item Type:	Article
Uncontrolled Keywords:	Vanillin, Piperidin-4-one oxime, Phenyl esters, Piperidin-4-one oxime ester, Antioxidants, Antimicrobials
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	12 Jul 2019 05:22
Last Modified:	12 Jul 2019 05:22
URI:	http://eprints.uni-mysore.ac.in/id/eprint/5101

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