Synthesis and antileishmanial activity of the core structure of cristaxenicin A

Hitoshi Fumiyama, Tomoko Sadayuki, Yasutaka Osada, Yasuyuki Goto, Yoichi Nakao, Seijiro Hosokawa

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The core structure of cristaxenicin A having trans-fused dihydropyran and nine membered ring has been synthesized and evaluated the antileishmanial activity. The dihydropyran ring was synthesized by [4+2] cycloaddition reaction between an unsaturated aldehyde and a β-alkoxy-α,β-unsaturated ketone. The nine membered ring possessing α,β-unsaturated aldehyde was constructed by the intramolecular NHK reaction followed by the Mitsunobu rearrangement. The racemic core structure of cristaxenicin A was evaluated the anti-leishmanial activity with an IC50value of 2.4 μM.

Original languageEnglish
Pages (from-to)4355-4357
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume26
Issue number17
DOIs
Publication statusPublished - 2016

Keywords

  • Antileishmanial
  • Cristaxenicin A
  • Nine-membered ring
  • Synthesis
  • [4+2] cycloaddition

ASJC Scopus subject areas

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

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