Synthesis and Free Radical-scavenging Activities of Di-mannich Bases of Cyclovalone Derivatives

Hayun, Catur Jatmika, Euis Maras Purwati, Sandi Salim, Rosita Kurniawan, Elizabeth Greffiana Chandra, Adam Arditya Fajriawan, Aulika Desthahrina Nareswara

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Novel di-Mannich bases of cyclovalone derivatives (1) have been synthesized and evaluated their antioxidant activity using DPPH free radical-scavenger method. The structures of the compounds were confirmed on the basis of FT-IR, 1H-NMR, 13C-NMR and mass spectral data. The result of antioxidant evaluation showed that di-Mannich derivative of cyclovalone with diethylamine ((2E,6E)-2,6-bis({3-[(diethylamino)methyl]-4-hydroxy-5-methoxyphenyl} methylidene) cyclohexan-1-one) (2a) exhibited the highest antioxidant activity with IC50 = 39.0 µM. Structure-activity relationship study showed that the higher pKa of the Mannich base, the higher activity (the lower IC50) of the compound.

Original languageEnglish
Pages (from-to)2742-2757
Number of pages16
JournalOriental Journal of Chemistry
Volume33
Issue number6
DOIs
Publication statusPublished - 1 Jan 2017

Keywords

  • Antioxidant
  • Cyclovalone
  • Mannich base
  • Radical scavenger
  • Synthesis

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