Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities

Midori A. Arai, Yuuki Kofuji, Yuuki Tanaka, Natsuki Yanase, Kazuki Yamaku, Rolly G. Fuentes, Utpal Kumar Karmakar, Masami Ishibashi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Rocaglamides are bioactive natural compounds which have a cyclopenta[b]benzofuran core structure. The total synthesis of a reported natural product, 3′-hydroxymethylrocaglate (5), was achieved using [3 + 2] cycloaddition between 3-hydroxyflavone and methyl cinnamate. We also describe the synthesis of rocaglamide heterocycle derivatives and evaluate their Wnt signal inhibitory activities. Compounds 4, 5, 22a, 22b, 22c and 23c showed potent Wnt signal inhibitory activity.

Original languageEnglish
Pages (from-to)3061-3068
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number11
DOIs
Publication statusPublished - 2016 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Arai, M. A., Kofuji, Y., Tanaka, Y., Yanase, N., Yamaku, K., Fuentes, R. G., Karmakar, U. K., & Ishibashi, M. (2016). Synthesis of rocaglamide derivatives and evaluation of their Wnt signal inhibitory activities. Organic and Biomolecular Chemistry, 14(11), 3061-3068. https://doi.org/10.1039/c5ob02537k