Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Papers
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
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1998 年 62 巻 8 号 p. 1568-1573

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  (-)-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.
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© 1998 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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