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Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

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

Author(s): Atul Gupta, Resmi Raghunandan, Atul Kumar, Prakash R. Maulik, Anila Dwivedy, Govind Keshri, Man Mohan Singh and Suprabhat Ray

Volume 3, Issue 5, 2007

Page: [446 - 454] Pages: 9

DOI: 10.2174/157340607781745483

Price: $65

Abstract

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).

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


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