Journal
ACS COMBINATORIAL SCIENCE
Volume 14, Issue 6, Pages 347-351Publisher
AMER CHEMICAL SOC
DOI: 10.1021/co300034y
Keywords
linker; solid-phase synthesis; library; hydroxy acetylenic compounds; steroids
Funding
- Canadian Institutes of Health Research
- Quebec Breast Cancer Foundation
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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.
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