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Synthesis of 3-phenyl-4-phenylvinyl Benzopyranones and the Corresponding 2,2-dimethyl-benzopyrans with Structural Similarity to Estradiol, as Estrogen Receptor Ligands

[ Vol. 3 , Issue. 5 ]


Atul Gupta, Resmi Raghunandan, Atul Kumar, Prakash R. Maulik, Anila Dwivedy, Govind Keshri, Man Mohan Singh and Suprabhat Ray   Pages 446 - 454 ( 9 )


7-Methoxy-3-phenyl-4-phenylvinyl benzopyran-2-ones and the corresponding 2,2-dimethyl-benzopyrans, substituted with different alkylamino residues were synthesized. Except compound 13e, all compounds showed high level of estrogen agonistic activity ( > 81 %) whereas, compounds 13 b-e and 15a showed significant estrogen antagonistic activity ( > 20 %). X-Ray analysis of a 7-methoxy-3-phenyl-4-phenylvinyl benzopyran-2-one derivative 13d showed its structural resemblance to endogenous estrogen, 17β-estradiol. Estrogenic and antiestrogenic activities of these derivatives demonstrate their estrogen receptor (ER) binding ability. The lack of hydroxyl groups at appropriate positions resulted in poor Relative Binding Affinity (RBA).


Antiestrogens, estrogen agonists, estrogen antagonists, estrogen receptor (ER), RBA, LBD(ligand binding domain)


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