Bioisostere of valtrate, anti-HIV principle by inhibition for nuclear export of Rev

Satoru Tamura, Nobuhiro Shimizu, Katsuaki Fujiwara, Masafumi Kaneko, Tominori Kimura, Nobutoshi Murakami

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Rational design by the MO calculation disclosed 5,6-dihydrovaltrate (2) as the bioisostere of valtrate (1), the Rev-export inhibitor with anti-HIV activity. The synthesis of 2 was accomplished by ingenious use of asymmetric Diels-Alder reaction and stereoselective epoxidation associated with the adjacent hydroxyl group. Because of similar biological potency to 1, the analog 2 should be recognized as a promising scaffold for new anti-HIV agents with an unprecedented mechanism of action, inhibition for nuclear export of Rev protein, in the conventional remedy.

Original languageEnglish
Pages (from-to)2159-2162
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number7
DOIs
Publication statusPublished - 2010 Apr 1

Keywords

  • Anti-HIV
  • Bioisostere
  • Iridoid
  • Rev-export inhibitor
  • Valtrate

ASJC Scopus subject areas

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

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