Synthesis and biological activities of (-)-6-n-octyl-indolactam-V, a new potent analogue of the tumor promoter (-)-indolactam-V.

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.

• Authors: Y Nakagawa, K Irie, Y Nakamura, H Ohigashi, H Hayashi
• Journal: Bioscience, biotechnology, and biochemistry (Biosci Biotechnol Biochem) Vol. 62 Issue 8 Pg. 1568-73 (Aug 1998) ISSN: 0916-8451 [Print] England
• PMID: 9757563 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 6-bromo-indolactam V
• 6-n-octyl-indolactam V
• Antigens, Viral
• Carcinogens
• Epstein-Barr virus early antigen
• Indoles
• Lactams
• Superoxides
• Phorbol 12,13-Dibutyrate
• Palladium
• indolactam V
• Protein Kinase C

Topics

• Antigens, Viral (pharmacology)
• Carcinogens (chemical synthesis, pharmacology)
• Chromatography, Gel
• Chromatography, High Pressure Liquid
• Indoles (chemistry, metabolism, pharmacology)
• Lactams (chemistry, metabolism, pharmacology)
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Optical Rotation
• Palladium (chemistry)
• Phorbol 12,13-Dibutyrate (metabolism)
• Protein Kinase C (drug effects)
• Spectrophotometry, Ultraviolet
• Streptomycetaceae (metabolism)
• Superoxides (analysis)
• Surface Properties