Isobrassinin and its analogues: novel types of antiproliferative agents.
Isobrassinin (2-(S-methyldithiocarbamoylaminomethyl)indole (7a), a regioisomer of the cruciferous phytoalexin brassinin (1), exerted marked antiproliferative effects on the HeLa, A431 and MCF7 cell lines (>78.6% inhibition at 30muM). For structure-activity relationships, further analogues were synthesized. The highest cytotoxic effect was displayed by 2-phenylimino-1,3-thiazino[5,6-b]indole (10) (10 microM, 76.8%-HeLa and 46.3%-MCF7). The effect of the natural phytoalexin brassinin was also determined.
Csomós
Péter
P
Institute of Pharmaceutical Chemistry, University of Szeged and Research Group for Heterocyclic Chemistry, Hungarian Academy of Sciences, H-6701, PO Box 427, Hungary.
Zupkó
István
I
Réthy
Borbála
B
Fodor
Lajos
L
Falkay
George
G
Bernáth
Gábor
G
D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D001943:Breast Neoplasms; D002455:Cell Division / Q000187:drug effects*; D045744:Cell Line, Tumor; D005260:Female; D006367:HeLa Cells; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D013329:Structure-Activity Relationship; D013859:Thiocarbamates / Q000737:chemistry / Q000494:pharmacology*; D000094162:Phytoalexins
D000970:Antineoplastic Agents; D007211:Indoles; D013859:Thiocarbamates; C089020:brassinin; D000094162:Phytoalexins