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.

• Authors: Y Nakagawa, K Irie, Y Nakamura, H Ohigashi, H Hayashi
• Journal: Bioscience, biotechnology, and biochemistry (Biosci Biotechnol Biochem) Vol. 61 Issue 8 Pg. 1415-7 (Aug 1997) ISSN: 0916-8451 [Print] England
• PMID: 9301127 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Carcinogens
• Indoles
• Lactams
• Lactones
• indolactone V
• indolactam V
• Protein Kinase C

Topics

• Carcinogens (chemistry, metabolism, pharmacology)
• Herpesvirus 4, Human (drug effects)
• Indoles (chemistry, metabolism, pharmacology)
• Lactams (chemistry, metabolism, pharmacology)
• Lactones (chemistry, metabolism, pharmacology)
• Magnetic Resonance Spectroscopy
• Models, Structural
• Molecular Conformation
• Protein Kinase C (metabolism)