[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.