Halogenated analogs of 1′-acetoxychavicol acetate, Rev-export inhibitor from Alpinia galanga, designed from mechanism of action

Satoru Tamura, Atsushi Shiomi, Tominori Kimura, Nobutoshi Murakami

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

In the course of search for the robust analogs of 1′-acetoxychavicol acetate (ACA, 1), the Rev-export inhibitor from the medicinal plant Alpinia galanga, we clarified formation of the quinone methide intermediate ii to be essential for exerting the inhibitory activity of 1. Based on this mechanism of action, the rational design from the MO calculation of the conclusive activation energy to ii resulted in the four halogenated analogs with more potent activity than ACA (1). In particular, the difluoroanalog 20d exhibited approximately four-fold potent activity as compared with 1.

Original languageEnglish
Pages (from-to)2082-2085
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number7
DOIs
Publication statusPublished - 2010 Apr 1

Keywords

  • 1′-Acetoxychavicol acetate
  • Evidence-based design
  • Halogenated analog
  • Quinone methide
  • Rev-export inhibitor

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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