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

J Nat Prod. 2019 Jun 28;82(6):1710-1713. doi: 10.1021/acs.jnatprod.8b00318. Epub 2019 May 24.

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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Cyclooxygenase 1 / chemistry*
  • Cyclooxygenase 1 / metabolism
  • Cyclooxygenase 2 / chemistry*
  • Cyclooxygenase 2 / metabolism
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / pharmacology*
  • Molecular Structure
  • Naproxen / chemistry
  • Naproxen / pharmacology*
  • Santonin / chemistry
  • Santonin / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase Inhibitors
  • Santonin
  • Naproxen
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • PTGS1 protein, human