Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

Using 3β-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse...

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Veröffentlicht in:Bioorganic & medicinal chemistry 2013-09, Vol.21 (18), p.5794-5798
Hauptverfasser: Saini, Ratni, Kataeva, Olga, Schmidt, Arndt W., Wang, Yuqin, Meljon, Anna, Griffiths, William J., Knölker, Hans-Joachim
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Sprache:eng
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Zusammenfassung:Using 3β-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2013.07.015