Synthesis of 7-substituted indolactam-V : An introduction of hydrophobic moieties on the indole ring
✍ Scribed by Yasuyuki Endo; Yasuo Sato; Koichi Shudo
- Book ID
- 104204224
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 641 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Indolactam-V, which shares the same partial structure of teleocidins A and B, shows a weak promoting activity compared to teleocidins.
It suggests that the hydrophobic moieties substituted on the 6,7positions of teleocidins play a role in increasing the biological activity.
7-Substituted indolactam-Vs have been synthesized starting from indolactam-V by two methods for preparation, which consisted of Friedel-Crafts alkylation and palladium cqtalyzed vinyl coupling reaction.
Teleocidins (e.q. teleocidin B-4,' 1, teleocidin A-l,* 2) are potent skin tumor-promoters.3 (-)-Indolactam-V (Al4 which is a common portion of the teleocidin molecule has attracted synthetic5 and stereochemical interest.
(-)-Indolactam-V (1) itself shows a weak tumor promoting activity compared to teleocidins in a two-stage carcinogenesis experiment on mouse skin.'l 16 17