Synthesis and biological activities of new conformationally fixed analogues of (-)-indolactam-V, the core structure of tumor-promoting teleocidins

Kazuhiro Irie, Fumito Koizumi, Yoriko Iwata, Takashi Ishii, Yoshiaki Yanai, Yoshimasa Nakamura, Hajime Ohigashi, Paul A. Wender

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12 Citations (Scopus)


(-)-Indolactam-V (1) exists as two stable conformers, the twist and the sofa form, in solution at room temperature. 3-Aza-Cope rearrangement of (-)-N13-desmethyl-N13-allylindolactam-V (5) gave new conformationally restricted analogues (2a and 3) along with a normal rearrangement product (7). Both 2a and 3, whose fixed conformation was the twist form, showed significant biological activities related to tumor promotion.

Original languageEnglish
Pages (from-to)453-458
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Issue number5
Publication statusPublished - Mar 2 1995
Externally publishedYes


ASJC Scopus subject areas

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

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