The syntheses of 3 beta-steroidal diacylglyceryl sulfides, sulfoxides, and sulfones.
The syntheses of the diacylglyceryl-sulfide 4a, sulfoxide 4b, and sulfone 4c of dehydroepiandrosterone (3 beta-hydroxyandrost-5-en-17-one, DHEA, 1a) are described. Nucleophilic substitution of 1,2-dipalmitoyl-3-iodo-rac-3-deoxyglycerol (2) with 3 beta-mercaptoandrost-5-en-17-one (3) afforded the diacylglyceryl-sulfide (4). Selective oxidation of 4 with m-chloroperbenzoic acid gave the diacylglyceryl-sulfoxide 4b and diacylglyceryl-sulfone 4c of DHEA. The sulfide 4a was a very weak inhibitor of glucose-6-phosphate dehydrogenase, whereas the sulfone 4c did not inhibit the enzyme.
Williams
J R
JR
Department of Chemistry, Temple University, Philadelphia, PA 19122-2585, USA.
Boehm
J C
JC
D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D005954:Glucosephosphate Dehydrogenase / Q000037:antagonists & inhibitors*; D013450:Sulfones / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000494:pharmacology
C097452:3-(1,2-di-O-palmitoylglycero)sulfinylandrost-5-en-17-one; C097453:3-(1,2-di-O-palmitoylglycero)sulfonylandrost-5-en-17-one; C097451:3-(1,2-di-O-palmitoylglycero)thioandrost-5-en-17-one; D013450:Sulfones; D013454:Sulfoxides; D003687:Dehydroepiandrosterone; D005954:Glucosephosphate Dehydrogenase