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

Salakatte Thammaiah Harini, Honnaiah Vijay Kumar, Sannenahalli Krishnegowda Peethambar, Javarappa Rangaswamy, Nagaraja Naik

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1887-1898
Number of pages12
JournalMedicinal Chemistry Research
Volume23
Issue number4
DOIs
StatePublished - Apr 2014
Externally publishedYes

Keywords

  • 2,6-Bis(4-methoxyphenyl)-1-methylpiperidin-4-one oxime esters
  • Antimicrobial studies
  • Antioxidant
  • Substituted benzoyl chlorides

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