Synthesis, characterization, and estrogen receptor binding affinity of flavone-, indole-, and furan-estradiol conjugates.
Different flavone-, indole-, and furan-17beta-estradiol conjugates, linked via alkyl spacer chains extending from the 17alpha-position of the estradiol moiety, were synthesized by Pd-catalyzed cross-coupling reactions. Structures were assigned based on spectroscopic data. In vitro competitive binding assays for the estrogen receptor (alpha-ER), using [(3)H]estradiol (RBA=100) as a competitor, revealed that a two-carbon alkyl linker combined with a flavone conjugate provided the highest binding affinity (RBA approximately 9), warranting further studies on their potential use as selective estrogen-receptor modulators (SERMs) for hormone-replacement therapies.
Ahmed
Naseem
N
Department of Nuclear Medicine and Radiobiology, Faculty of Medicine and Health Sciences, Université de Sherbrooke, Sherbrooke, QC, Canada J1H 5N4.
Dubuc
Celena
C
Rousseau
Jacques
J
Bénard
Francois
F
van Lier
Johan E
JE
D001667:Binding, Competitive; D002384:Catalysis; D004958:Estradiol / Q000737:chemistry*; D047628:Estrogen Receptor alpha / Q000737:chemistry* / Q000187:drug effects; D004966:Estrogens, Conjugated (USP) / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D047309:Flavones / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D020845:Selective Estrogen Receptor Modulators / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D047628:Estrogen Receptor alpha; D004966:Estrogens, Conjugated (USP); D047309:Flavones; D005663:Furans; D007211:Indoles; D020845:Selective Estrogen Receptor Modulators; D004958:Estradiol; D010165:Palladium