title: New diethylsilylacetylenic linker for parallel solid-phase synthesis of libraries of hydroxy acetylenic steroid derivatives with improved metabolic stability.
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.
authors.affiliation: Laboratory of Medicinal Chemistry, CHUQ (CHUL) Research Center , 2705 Laurier Boulevard, Quebec, QC, G1V 4G2, Canada.
authors.forename: Amélie
authors.initials: A
authors.lastname: Talbot
authors.forename: René
authors.initials: R
authors.lastname: Maltais
authors.forename: Donald
authors.initials: D
authors.lastname: Poirier
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000480:Alkynes; D054852:Small Molecule Libraries; D013256:Steroids