Concise synthesis of 5,6-dihydrovaltrate leading to enhanced Rev-export inhibitory congener

Satoru Tamura, Katsuaki Fujiwara, Nobuhiro Shimizu, Shingo Todo, Nobutoshi Murakami

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The concise synthesis of 5,6-dihydrovaltrate (2), the bioisostere of valtrate (1) showing anti-HIV activity by inhibition for nuclear export of Rev, has been achieved from the commercially available iridoid genipin (3). Analysis of steric influence of the substituents linked to the three hydroxyl groups was conducted by the synthesized three analogs (2a-2c). Consequently, attenuation of steric hindrance around the epoxy portion was revealed to enhance inhibitory potency for Rev-export. In addition to this finding, 1-acetoxy analog 2b was disclosed as the promising Rev-export inhibitor superior to 1.

Original languageEnglish
Pages (from-to)5975-5980
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number16
DOIs
Publication statusPublished - 2010 Aug 15

Keywords

  • 5,6-Dihydrovaltrate
  • Anti-HIV
  • Genipin
  • Iridoid
  • Rev-export inhibitor

ASJC Scopus subject areas

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

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