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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 ]

Author(s):

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

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)

Affiliation:

16/3 kha Sarojni Naidu Marg,Behind- Masonic Lodge, Hazratganj, Lucknow, India.



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