Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans.
Basic Information
ID: ALA1125031
Journal: J Med Chem
Title: Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans.
Authors: Saeed A, Sharma AP, Durani N, Jain R, Durani S, Kapil RS.
Abstract: A series of 2,3-diaryl-1-benzopyran analogues substituted at position 4 of 2-phenyl with a hydroxy or pyrrolidinoethoxy residue were synthesized as models for (E)-triarylpropenones constrained in the s-trans conformation. The prototypes, belonging to five chemical series, were evaluated for their estrogen receptor affinity and for estrogen agonist-antagonist activities. The 4H-1-benzopyran-4-one, the 2,3-dihydro-4H-1-benzopyran-4-one, the 4H-1-benzopyran, and the 2,3-dihydro-1-benzopyran derivatives were found to be inactive or only marginally activate as receptor ligands or estrogen agonists-antagonists. In the 2H-1-benzopyran category the parent phenol was also inactive whereas the basic ethers 16 and 26 were modest receptor ligands while being quite active as antiestrogens. In a comparative study the benzopyran 16 was found to be more effective antiestrogen than tamoxifen while being as effective as LY-117018. The benzopyrans have thus emerged as a new class of potent antiestrogens.
CiteXplore: 2258906
DOI: 10.1021/jm00174a018
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