Synthesis and structure-activity relationship study of lamellarin derivatives.
Ten derivatives (3-12) of marine alkaloid lamellarin D (1) were synthesized and evaluated for cytotoxicity against a HeLa cell line in an effort to examine their structure-activity relationships. It appeared that the hydroxyl groups at positions C-8 and C-20 of 1 were important structural requirements for cytotoxic activity, while the hydroxyl group at C-14 and the two methoxy groups at C-13 and C-21 were not necessary for the activity.
Ishibashi
Fumito
F
Division of Marine Life Science and Biochemistry, Faculty of Fisheries, and Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan. fumito@net.nagasaki-u.ac.jp
Tanabe
Shinji
S
Oda
Tatsuya
T
Iwao
Masatomo
M
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D002522:Chlorocebus aethiops; D003374:Coumarins; D004285:Dogs; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006576:Heterocyclic Compounds, 4 or More Rings; D006801:Humans; D007546:Isoquinolines; D007668:Kidney; D016685:Mitomycin / Q000494:pharmacology; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051381:Rats; D012509:Sarcoma; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects; D002583:Uterine Cervical Neoplasms
D000470:Alkaloids; D003374:Coumarins; D006576:Heterocyclic Compounds, 4 or More Rings; D007546:Isoquinolines; D011758:Pyrroles; C455554:lamellarin D; C455555:lamellarin H; D016685:Mitomycin