title: Synthesis of 3-phenyl-4-phenylvinyl benzopyranones and the corresponding 2,2-dimethyl-benzopyrans with structural similarity to estradiol, as estrogen receptor ligands.
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, 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).
authors: Medicinal and Process Chemistry Division, Central Drug Research Institute, Lucknow, India. atisky2001@yahoo.co.in
authors: Atul
authors: A
authors: Gupta
authors: Resmi
authors: R
authors: Raghunandan
authors: Atul
authors: A
authors: Kumar
authors: Prakash R
authors: PR
authors: Maulik
authors: Anila
authors: A
authors: Dwivedyc
authors: Govind
authors: G
authors: Keshri
authors: Man Mohan
authors: MM
authors: Singh
authors: Suprabhat
authors: S
authors: Ray
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D004958:Estradiol / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011960:Receptors, Estrogen / Q000378:metabolism*; D013055:Spectrophotometry, Infrared
chemical_list: D001578:Benzopyrans; D011960:Receptors, Estrogen; D004958:Estradiol