207672-42-2Relevant articles and documents
Synthesis of 4α-(2-propenyl)-5,6-secocholestan 3α-ol, a novel B-ring seco analog of the hypocholesterolemic agent 4α-(2-propenyl)-5α-cholestan- 3α-ol
Lin, Ho-Shen,Rampersaud, Ashraff A.,Richett, Michael E.,Beavers, Lisa S.,McClure, Don B.,Gadski, Robert A.
, p. 202 - 207 (1998)
4α-(2-Propenyl)-5α-cholestan-3α-ol (LY295427) was previously identified from a CHO cell-based assay to be a potent LDL receptor up- regulator and had demonstrated to be an effective agent in lowering plasma cholesterol levels in hypercholesterolemic hamsters. In order to investigate the effect of flexibility of the 3α-hydroxy-bearing A-ring on the activity, 4α-(2-propenyl)-5,6-secocholestan-3α-ol (11), a B-ring seco analog of LY295427, is thus synthesized from cholest-4-en-3-one. Test results indicate that 11 is not active in the CHO cell-based LDL receptor/luciferase assay at concentrations up to 20 μg/mL. The result underlines the importance of maintaining the A-B-C-D ring rigidity of the 3α-sterols in terms of binding to the putative oxysterol receptor.