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

Autor:	Ashraff A. Rampersaud, Mcclure Don B, Ho-Shen Lin, Lisa Selsam Beavers, Michael Enrico Richett, Robert Alan Gadski
Rok vydání:	1998
Předmět:	Pharmacology Propenyl Oxysterol Bicyclic molecule Stereochemistry Chemistry Chinese hamster ovary cell medicine.medical_treatment Organic Chemistry Clinical Biochemistry Biochemistry Chemical synthesis Steroid Endocrinology LDL receptor medicine Receptor Molecular Biology
Zdroj:	Steroids. 63:202-207
ISSN:	0039-128X
DOI:	10.1016/s0039-128x(98)00004-x
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::37cc5e6f2135bb109a7387a34fdef80d https://doi.org/10.1016/s0039-128x(98)00004-x Zobrazit plný text záznamu Full Text from ScienceDirect