Synthesis and Biological Activities of (-)-6-n-Octyl-indolactam-V, a New Potent Analogue of the Tumor Promoter (-)-Indolactam-V

Yu Nakagawa, Kazuhiro Irie, Yoshimasa Nakamura, Hajime Ohigashi, Hideo Hayashi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

(-)-Indolactam-V (1) without a hydrophobic chain at positions 6 and 7 of the indole ring is a weak tumor promoter compared with teleocidin Bs. To investigate the effects of the hydrophobic substituent at position 6 of teleocidin Bs, we synthesized (-)-6-n-octyl-indolactam-V (2) by a palladium-catalyzed coupling reaction from (-)-6-bromo-indolactam-V (7) which had been obtained by microbial conversion with Streptoverticillium blastmyceticum NA34-17 as the key step. (-)-7-n-Octyl-indolactam-V (3) with potent biological activities comparable to those of teleocidin Bs was similarly synthesized from (-)-7-bromo-indolactam-V as a positive control. Compound 2 showed similar biological activities to those of 3, indicating that the effect of the hydrophobic substituent at position 6 of 1 was identical to that at position 7.

Original languageEnglish
Pages (from-to)1568-1573
Number of pages6
JournalBioscience, Biotechnology and Biochemistry
Volume62
Issue number8
DOIs
Publication statusPublished - Jan 1 1998
Externally publishedYes

Keywords

  • (-)-6-n-octyl-indolactam-V
  • Epstein-Barr virus
  • Protein kinase C
  • Teleocidin
  • Tumor promoter

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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