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Medicinal Chemistry Research

, Volume 23, Issue 4, pp 1887–1898 | Cite as

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 KumarEmail author
  • Sannenahalli Krishnegowda Peethambar
  • Javarappa Rangaswamy
  • Nagaraja NaikEmail author
Original Research

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 (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.

Keywords

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

Notes

Acknowledgments

The authors are thankful to NMR Research Center, Indian Institute of Science, Bangalore for providing spectral data.

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Salakatte Thammaiah Harini
    • 1
  • Honnaiah Vijay Kumar
    • 2
    Email author
  • Sannenahalli Krishnegowda Peethambar
    • 3
  • Javarappa Rangaswamy
    • 1
  • Nagaraja Naik
    • 1
    Email author
  1. 1.Department of Studies in ChemistryUniversity of MysoreMysoreIndia
  2. 2.Department of Organic ChemistryIndian Institute of ScienceBangaloreIndia
  3. 3.Department of BiochemistryKuvempu UniversityShimogaIndia

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