Synthesis and biological activities of indolactone-V, the lactone analogue of the tumor promoter (-)-indolactam-V.
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.
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
D002273:Carcinogens / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D004854:Herpesvirus 4, Human / Q000187:drug effects; D007211:Indoles / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D007769:Lactams / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D007783:Lactones / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008961:Models, Structural; D008968:Molecular Conformation; D011493:Protein Kinase C / Q000378:metabolism
D002273:Carcinogens; D007211:Indoles; D007769:Lactams; D007783:Lactones; C108903:indolactone V; C043969:indolactam V; D011493:Protein Kinase C