Synthesis of dehydroepiandrosterone sulfatide and 16 alpha-halogenated steroids.
Dehydroepiandrosterone sulfatide was prepared in a 68% yield by the reaction of 5-androstene-3 beta-ol-17-one 3 sulfate (silver salt) with dipalmitoyl alpha-iodopropylene glycol. The sulfatide was found to be a more potent inhibitor of human glucose-6-phosphate dehydrogenase than dehydroepiandrosterone. 16 alpha-Halogenated steroids also were prepared by direct halogenation of the steroid or indirect halogenation of an appropriate steroidal intermediate. Among various halogenated steroids, 16 alpha-bromoepiandrosterone was 50 times as potent as dehydroepiandrosterone as an inhibitor of glucose-6-phosphate dehydrogenase.
D000818:Animals; D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004912:Erythrocytes / Q000201:enzymology; D005954:Glucosephosphate Dehydrogenase / Q000037:antagonists & inhibitors; D006801:Humans; D051379:Mice; D013257:Steroids, Brominated / Q000138:chemical synthesis*; D013258:Steroids, Chlorinated / Q000138:chemical synthesis; D013259:Steroids, Fluorinated / Q000138:chemical synthesis; D013433:Sulfoglycosphingolipids / Q000138:chemical synthesis*
D013257:Steroids, Brominated; D013258:Steroids, Chlorinated; D013259:Steroids, Fluorinated; D013433:Sulfoglycosphingolipids; D003687:Dehydroepiandrosterone; D005954:Glucosephosphate Dehydrogenase