Synthesis and Biological Activities of Indolactone-V, the Lactone Analogue of the Tumor Promoter (–)-Indolactam-V

Abstract

The tumor promoter (–)-indolactam-V (1) exists in two stable conformers (twist and sofa) due to isomerization of the amide group. Indolactone-V (2), the lactone analogue of 1, has been synthesized to investigate the effects of the amide group on its conformation and biological activities. Indolactone-V (2) existed only as the inactive sofa-like conformer, indicating that the amide group of 1 plays a critical role in formation of the active twist conformation. © 1997, Taylor & Francis Group, LLC. All rights reserved.