[3-Substituted 2-phenylindoles: synthesis and biological properties].
Knoevenagel-reaction of indol-3-carbaldehydes 5a,b and 7a,b with nitromethane leads to the nitroethenes 12 and 14, the analogous reaction with malodinitrile to the methylidenemalonic acid dinitriles 16.- Michael-addition of nitromethane at 12 and 14 affords the 1,3-dinitropropanes 13 and 15, reduction of 16 the methylmalonic acid dinitriles 17.- Reaction of indoles 3 with n-BuLi/phenylsulfonylchloride leads to the 3-chloroindoles 18, reaction with NaH/ethyliodide, either cleavage and acylation to derivatives 19.- Compounds 7-11, 14-17, and 19 show affinity to the estrogen receptor. Compounds 7b, 9-11, 17b, and 19b inhibit the growth of MCF-7- and MDA-MB-231-cells. IC50-values are determined and structure-activity relationships are discussed.
Mahboobi
S
S
Institut für Pharmazie der Universität Regensburg.
Grothus
G
G
von Angerer
E
E
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D011960:Receptors, Estrogen / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007211:Indoles; D011960:Receptors, Estrogen
3-Substituierte 2-Phenylindole: Synthese und biologische Eigenschaften.