Syntheses of ring C oxysterols: inhibitors of sterol biosynthesis.
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.
Parish
Edward J
EJ
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 336849, USA, parisej@auburn.edu
Luo
Chi
C
Webb
Thomas
T
Gorden
John D
JD
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006903:Hydroxymethylglutaryl CoA Reductases / Q000187:drug effects / Q000378:metabolism*; D013261:Sterols / Q000138:chemical synthesis / Q000737:chemistry
D004791:Enzyme Inhibitors; D013261:Sterols; D006903:Hydroxymethylglutaryl CoA Reductases