Synthetic Estrogens. Halotriphenylethylene Derivatives

Clomiphene Citrate-Initiated Ovulation: A Clinical Update

“…It is noteworthy that triphenylethylenes and triphenylchloroethylenes have long been known as estrogen agonists of low potency but of unusually long duration of action in the castrate or immature rodent. [56][57][58] Moreover, these traits have been repeatedly shown to be augmented by an alkoxy substitution. Paradoxically, however, these early observations received relatively little attention until the "rediscovery" that clomiphene citrate may act as an estrogen, rather than an antiestrogen, in several species, including the human.…”

Synthesis and evaluation of 2-halogenated-1,1-bis(4-hydroxyphenyl)-2-(3-hydroxyphenyl)-ethylenes as potential estrogen receptor-targeted radiodiagnostic and radiotherapeutic agents

“…Although one can halo- warmed to ambient temperature and ice water (10 mL) was added. 399 The resulting mixture was partitioned between EtOAc (300 mL) and lation of the bromo-derivative followed by addition of iodine [44]. ligands [46].…”

“…Preliminary results were highly encouraging and 101 therefore it was necessary to prepare more material not only for 102 further biological assays, but to provide precursors for its use in 103 radiological studies. 104 The synthetic strategy was based upon the general synthesis of 105 triarylethylenes [44,45] (Scheme 1). It was of further interest 106 because the preparation of 1,1,bis(4-hydroxyphenyl)-2-(3-hydroxy 107 phenyl)ethylenes, unlike the corresponding 2-(4-hydroxyphenyl) 108 isomers, had not been well described [46].…”

“…The predicted 570 binding energies (YASARA) or GLIDEscores (GLIDE) were recorded.571 When inspecting ligand-receptor contacts, hydrogen bonds as well 572 as contacts between the halogen atom (or vinyl proton) in the non-573 steroidal ligands and the receptor were considered. GLIDE defines 574 ''good'' contacts as those whose cutoff ratios (defined by the equa-575 tion C = D 1,2 /(R 1 + R 2 ), where C = cutoff ratio, to proceed readily[44,45], however, when the meth-594 oxy on the 2-phenyl group is meta-rather than para-, reagent stoi-595 chiometry and temperature were key factors in determining the 596 formation of the desired product. Initial halogenation occurs at the 597 olefinic 2-position, however, halogenation on the meta-substituted 598 aryl ring becomes a competing reaction as the concentration of start-599 ing material decreases.…”

Lithium aluminium hydride reduction of some triarylvinyl bromides and acetates catalyzed by some transition metal chlorides

“…The various vinylic substrates were prepared according to literature procedures (7)(8)(9)(10)(11)(12)(13). The reactions were performed as illustrated by the following typical procedures.…”