Synthesis and biochemical screening of phenylselenium-substituted steroid hormones.
The syntheses of phenylselenium-substituted progesterone [21- (1) and 17 alpha-(phenylseleno)progesterone (2)] and testosterone [16 beta- (3) and 16 alpha-(phenylseleno)testosterone (4)] derivatives are described, along with data which help to establish the stereochemistry of the substituents in the testosterone molecules. Except for 21-(phenylseleno)-progesterone, the molecules exhibit greatly reduced receptor-binding capabilities.
D000818:Animals; D003600:Cytosol / Q000378:metabolism; D005260:Female; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D011374:Progesterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D011817:Rabbits; D051381:Rats; D011987:Receptors, Steroid / Q000378:metabolism; D012643:Selenium; D013739:Testosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D009942:Organometallic Compounds; D011987:Receptors, Steroid; D013739:Testosterone; D011374:Progesterone; D012643:Selenium