New diethylsilylacetylenic linker for parallel solid-phase synthesis of libraries of hydroxy acetylenic steroid derivatives with improved metabolic stability

ACS Combinatorial Science
Amélie TalbotDonald Poirier

Abstract

Acetylenic tertiary alcohols are well-known to be compounds that are biologically more stable than their corresponding secondary alcohols. The linkage of an acetylenic compound to a polymer support and further introduction of molecular diversity was found to be an interesting way to generate libraries of hydroxy acetylenic derivatives and thus potentially improve their biological properties. For the first time, we describe the loading of an ethynyl steroid to a polystyrene-diethylsilane resin and its uses for the solid-phase synthesis of a model library of 21 steroid derivatives. Two levels of molecular diversity were introduced by successive addition of amino acids and carboxylic acids, and hydroxy acetylenic steroids were then released by an acidic treatment in high yield and purity without further purification step.

References

Jul 31, 1999·Clinical Pharmacokinetics·S N de WildtJ N van den Anker
Apr 12, 2003·Environmental Science & Technology·Karen L ThorpeCharles R Tyler
Jun 30, 2004·Maturitas·John C Stevenson
Oct 28, 2004·Environmental Science & Technology·Marc M HuberUrs von Gunten
Aug 23, 2005·Climacteric : the Journal of the International Menopause Society·H Kuhl
May 14, 2008·Current Medicinal Chemistry·C M GalmariniB Joseph
Dec 4, 2009·Investigational New Drugs·Irene V BijnsdorpGodefridus J Peters

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