Transformation of Santonin to a Naproxen Analogue with Anti-Inflammatory Activity

Abstract

Santonin, a natural product, was aromatized with molecular iodine as the catalyst. The new compound was characterized as (S)-methyl-2-(7-hydroxy-5,8-dimethylnaphthalen-2-yl) propanoate (2) based on 2D NMR spectroscopic data. Structurally, compound 2 was highly similar to the anti-inflammatory drug naproxen. The new naproxen analogue had significant potency against cyclooxygenase 1 and 2 (IC50 = 31.0 and 66.1 μM, respectively). © 2019 American Chemical Society and American Society of Pharmacognosy.