Abstract

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

DOI : http://dx.doi.org/10.13005/ojc/330607

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.

Cyclovalone; Mannich base; Synthesis; Antioxidant; Radical scavenger

[ View HTML Full Text]