Practical synthesis of hydroxychromenes and evaluation of their biological activity

Jae Chul Jung, Seikwan Oh

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

A simple and efficient seven steps synthesis of brodifacoum and difethialone from phenylacetyl chloride is described. The key synthetic strategies involve Friedel-Crafts acylation, intramolecular ring cyclization and condensation reaction in the presence of Brønsted-Lowry acids. It was found that brodifacoum showed favorable inhibiting activities on LPS-stimulated nitrite production in BV-2 microglia cells. Brodifacoum exhibited superior anti-inflammatory effects than difethialone. We expect that an efficient linear synthesis of 4-hydroxycoumarin derivatives and key fragments that are useful agents for the modulation of inflammation as well as inhibition of coagulation will be of practical use.

Original languageEnglish
Pages (from-to)240-247
Number of pages8
JournalMolecules
Volume17
Issue number1
DOIs
StatePublished - Jan 2012

Keywords

  • Anti-inflammatory
  • Brodifacoum
  • Coupling reaction
  • Difethialone
  • Friedel-crafts acylation
  • Intramolecular ring cyclization reaction

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