Simple synthesis of modafinil derivatives and their anti-inflammatory activity

Jae Chul Jung, Yeonju Lee, Jee Young Son, Eunyoung Lim, Mankil Jung, Seikwan Oh

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

Abstract

Simple synthesis of modafinil derivatives and their biological activity are described. The key synthetic strategies involve substitution and coupling reactions. We determined the anti-inflammatory effects of modafinil derivatives in cultured BV2 cells by measuring the inhibition of nitrite production and expression of iNOS and COX-2 after LPS stimulation. It was found that for sulfide analogues introduction of aliphatic groups on the amide part (compounds 11a-d) resulted in lower anti-inflammatory activity compared with cyclic or aromatic moieties (compounds 11e-k). However, for the sulfoxide analogues, introduction of aliphatic moieties (compounds 12a-d) showed higher anti-inflammatory activity than cyclic or aromatic fragments (compounds 12e-k) in BV-2 microglia cells.

Original languageEnglish
Pages (from-to)10446-10458
Number of pages13
JournalMolecules
Volume17
Issue number9
DOIs
StatePublished - Sep 2012

Keywords

  • Anti-inflammation
  • Coupling reaction
  • Modafinil
  • Nitric oxide
  • S-alkylation

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