Role of the hydrophobic moiety of tumor promoters. Synthesis and activity of 2-alkylated benzolactams.
The size and position of a hydrophobic moiety on a benzolactam skeleton, which reproduces the active conformation and biological activity of teleocidins, play an important role in the appearance of the activity. Compounds with alkyl groups of various sizes and shapes at the 2-position of benzolactam were synthesized. Structure-activity results indicate that a hydrophobic substituent at the C-2 position plays a critical role in the appearance of biological activities, as in the case of substitution at C-9.
Endo
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Y
Graduate School of Pharmaceutical Sciences, University of Tokyo, Japan. yendo@mol.f.u-tokyo.ac.jp
Yokoyama
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A
D000478:Alkylation; D002273:Carcinogens / Q000138:chemical synthesis* / Q000378:metabolism / Q000633:toxicity*; D002454:Cell Differentiation / Q000187:drug effects; D002455:Cell Division / Q000187:drug effects; D006131:Growth Inhibitors / Q000138:chemical synthesis / Q000633:toxicity; D018922:HL-60 Cells; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D007700:Kinetics; D007769:Lactams / Q000138:chemical synthesis* / Q000378:metabolism / Q000633:toxicity*; D015240:Phorbol 12,13-Dibutyrate / Q000378:metabolism; D011493:Protein Kinase C / Q000037:antagonists & inhibitors / Q000378:metabolism; D051745:Protein Kinase C-delta; D013329:Structure-Activity Relationship
D002273:Carcinogens; D006131:Growth Inhibitors; D007527:Isoenzymes; D007769:Lactams; C113786:benzolactam V8-310; D015240:Phorbol 12,13-Dibutyrate; C497258:PRKCD protein, human; D011493:Protein Kinase C; D051745:Protein Kinase C-delta