Chemical synthesis of 4,4'-dimethyl-7-oxygenated sterols. Inhibitors of 3-hydroxy-3-methylglutaryl reductase |
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| Authors: | E J Parish S Chitrakorn F R Taylor S E Saucier |
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| Affiliation: | 1. Department of Chemistry, Auburn University Auburn University, AL 36849 USA;2. Jackson Laboratory, Bar Harbor, ME 04609 U.S.A. |
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| Abstract: | The chemical syntheses of 4,4'-dimethylcholest-5-en-3 beta-ol-7-one, 4,4'-dimethylcholest-5-ene-3 beta, 7 beta-diol and 4,4'-dimethylcholest-5-ene-3 beta, 7 alpha-diol are described. All of these compounds were found to be potent inhibitors of 3-hydroxy-3-methylglutaryl (HMG-CoA) reductase activity in cultured mouse L cells. The synthetic scheme developed in this study utilizes commercial cholesterol as the starting material and provides a simplified method for the preparation of 4,4'-dimethyl-7-oxygenated steroids. |
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| Keywords: | 7-oxysterol 4,4′-dimethyl 3-hydroxy-3-methylglutarly reductase 7-oxygenated sterol GLC gas liquid chromatography HMG-CoA 3-hydroxy-3-methlglutaryl SS solvent system TLC thin-layer chromatography |
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