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

Salakatte Thammaiah Harini, Honnaiah Vijay Kumar, Javarappa Rangaswamy, Nagaraja Naik

Research output: Contribution to journalArticle

45 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)7588-7592
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number24
DOIs
StatePublished - Dec 15 2012
Externally publishedYes

Keywords

  • Antimicrobials
  • Antioxidants
  • Phenyl esters
  • Piperidin-4-one oxime
  • Piperidin-4-one oxime ester
  • Vanillin

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