title: Syntheses of ring C oxysterols: inhibitors of sterol biosynthesis.
abstract: Oxygenated derivates of cholesterol and lanosterol, known as oxysterols, have consistently displayed significant activity as inhibitors of 3-hydroxy-3-methylglutaryl (HMG) CoA reductase, a key regulatory enzyme in sterol biosynthesis. We have developed the chemical syntheses of ring C oxysterols for evaluation as inhibitors of sterol biosynthesis. A key intermediate in the chemical synthesis was 3beta-benzoyloxy-9alpha, 1alpha-epoxy-5alpha-cholest-7-ene (1), whose structure was confirmed by X-ray crystallographic analysis and is presented herein.
authors: Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 336849, USA, parisej@auburn.edu
authors: Edward J
authors: EJ
authors: Parish
authors: Chi
authors: C
authors: Luo
authors: Thomas
authors: T
authors: Webb
authors: John D
authors: JD
authors: Gorden
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006903:Hydroxymethylglutaryl CoA Reductases / Q000187:drug effects / Q000378:metabolism*; D013261:Sterols / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D004791:Enzyme Inhibitors; D013261:Sterols; D006903:Hydroxymethylglutaryl CoA Reductases