Synthesis of 3-phenyl-4-phenylvinyl benzopyranones and the corresponding 2,2-dimethyl-benzopyrans with structural similarity to estradiol, as estrogen receptor ligands

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...

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Published inMedicinal chemistry (Shp-sariqah, United Arab Emirates) Vol. 3; no. 5; p. 446
Main Authors Gupta, Atul, Raghunandan, Resmi, Kumar, Atul, Maulik, Prakash R, Dwivedyc, Anila, Keshri, Govind, Singh, Man Mohan, Ray, Suprabhat
Format Journal Article
LanguageEnglish
Published Netherlands 01.09.2007
Subjects
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Benzopyrans - metabolism
Crystallography, X-Ray
Estradiol - chemistry
Estradiol - metabolism
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Receptors, Estrogen - metabolism
Spectrophotometry, Infrared
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Summary: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, 17beta-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).
ISSN:1573-4064
DOI:10.2174/157340607781745483