Synthesis and estrogen receptor binding affinities of 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-ones containing a basic side chain.
Two isoflavones containing a sulfur or oxygen hinge with an amine-bearing side chain have been designed and synthesized as potential selective estrogen receptor modulators. The target compounds exhibited low affinities for estrogen receptors (ERs), and binding affinity data indicate that oxygen hinge is more favorable than sulfur for binding. These compounds also displayed selectivity for ERalpha over ERbeta.
Kim
Young-Woo
YW
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus 43210, USA.
Mobley
James A
JA
Brueggemeier
Robert W
RW
D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D006801:Humans; D007700:Kinetics; D011485:Protein Binding; D011960:Receptors, Estrogen / Q000378:metabolism*; D020845:Selective Estrogen Receptor Modulators / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013629:Tamoxifen / Q000031:analogs & derivatives / Q000378:metabolism
D001578:Benzopyrans; D047628:Estrogen Receptor alpha; D047629:Estrogen Receptor beta; D011960:Receptors, Estrogen; D020845:Selective Estrogen Receptor Modulators; D013629:Tamoxifen