Synthesis and biological activities of (-)-6-n-octyl-indolactam-V, a new potent analogue of the tumor promoter (-)-indolactam-V.
(-)-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.
Nakagawa
Y
Y
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan.
Irie
K
K
Nakamura
Y
Y
Ohigashi
H
H
Hayashi
H
H
D000956:Antigens, Viral / Q000494:pharmacology; D002273:Carcinogens / Q000138:chemical synthesis / Q000494:pharmacology*; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D007211:Indoles / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D007769:Lactams / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009904:Optical Rotation; D010165:Palladium / Q000737:chemistry; D015240:Phorbol 12,13-Dibutyrate / Q000378:metabolism; D011493:Protein Kinase C / Q000187:drug effects; D013056:Spectrophotometry, Ultraviolet; D013306:Streptomycetaceae / Q000378:metabolism; D013481:Superoxides / Q000032:analysis; D013499:Surface Properties
C114898:6-bromo-indolactam V; C114899:6-n-octyl-indolactam V; D000956:Antigens, Viral; D002273:Carcinogens; C033305:Epstein-Barr virus early antigen; D007211:Indoles; D007769:Lactams; D013481:Superoxides; D015240:Phorbol 12,13-Dibutyrate; D010165:Palladium; C043969:indolactam V; D011493:Protein Kinase C