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The chemical synthesis of four stereoisomers (compounds 5a–d) of 16β-(m-carbamoylbenzyl)-estradiol, a potent reversible inhibitor of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1), and two intermediates (compounds 3a and b) was performed. Assignment of all nuclear magnetic resonance signals confirmed the stereochemistry at positions 13, 16 and 17. Nuclear overhauser effects showed clear correlations...
The 17β-hydroxysteroid dehydrogenases (17β-HSDs) are members of a family of enzymes that catalyze the interconversion of weakly active sexual hormones (ketosteroids) and potent hormones (17β-hydroxysteroids). Among the known isoforms of 17β-HSD, the type 1 catalyzes the NAD(P)H-mediated reduction of estrone (E 1 ) to estradiol (E 2 ), a predominant mitogen for the breast cancer cells...
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