Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates.
The 7-oxo derivative of dehydroepiandrosterone is more active than the parent steroid and is devoid of adverse side effects in rats, monkeys and humans. In anticipation of possible therapeutic use we have sought more active, longer lasting forms of 7-oxo- and 7beta-hydroxydehydroepiandrosterones. The 7-oxo- and 7-hydroxy steroids have been converted to glucuronides, ethers and carbonate esters. The syntheses of these compounds are described and their ability to induce the formation of liver thermogenic enzymes when fed to rats is reported. Some of the new derivatives were found to be somewhat more effective than the equimolar amounts of 7-oxo-DHEA with which they were compared in each experiment.
Marwah
P
P
Department of Biochemistry and Institute for Enzyme Research, University of Wisconsin-Madison, 53705, USA.
Marwah
A
A
Kneer
N
N
Lardy
H
H
D000818:Animals; D002254:Carbonates / Q000138:chemical synthesis / Q000494:pharmacology; D003687:Dehydroepiandrosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D004790:Enzyme Induction / Q000187:drug effects; D004987:Ethers / Q000138:chemical synthesis / Q000494:pharmacology; D020719:Glucuronides / Q000138:chemical synthesis / Q000494:pharmacology; D005993:Glycerolphosphate Dehydrogenase / Q000096:biosynthesis / Q000187:drug effects; D008099:Liver / Q000201:enzymology; D008291:Malate Dehydrogenase / Q000096:biosynthesis / Q000187:drug effects; D051381:Rats; D013329:Structure-Activity Relationship
D002254:Carbonates; D004987:Ethers; D020719:Glucuronides; D003687:Dehydroepiandrosterone; D005993:Glycerolphosphate Dehydrogenase; D008291:Malate Dehydrogenase