Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs

…, EC Hayes, CA DaSilva, S Warrier, J Yudkovitz…

Index: Tan, Qiang; Blizzard, Timothy A.; Morgan II, Jerry D.; Birzin, Elizabeth T.; Chan, Wanda; Yang, Yi Tien; Pai, Lee-Yuh; Hayes, Edward C.; Dasilva, Carolyn A.; Warrier, Sudha; Yudkovitz, Joel; Wilkinson, Hilary A.; Sharma, Nandini; Fitzgerald, Paula M.D.; Li, Susan; Colwell, Lawrence; Fisher, John E.; Adamski, Sharon; Reszka, Alfred A.; Kimmel, Donald; Dininno, Frank; Rohrer, Susan P.; Freedman, Leonard P.; Schaeffer, James M.; Hammond, Milton L. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 6 p. 1675 - 1681

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Citation Number: 40

Abstract

The discovery, synthesis, and SAR of chromanes as ERα subtype selective ligands are described. X-ray studies revealed that the origin of the ERα-selectivity resulted from a C-4 trans methyl substitution to the cis-2, 3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in vivo antagonism of estradiol in an immature rat uterine weight assay, effectively inhibited ovariectomy-induced bone resorption in a ...