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Parallel solid-phase synthesis of a model library of 7alpha-alkylamide estradiol derivatives as potential estrogen
M R Tremblay1, J Simard, D Poirier
1Medicinal Chemistry Division, Laboratory of Molecular Endocrinology, Laval University Medical Research Center, Quebec, Canada.
Abstract:
The C17-THP derivative of 7alpha-(11-azidoundecanyl)-estradiol (4) was synthesized and coupled to an aminomethyl resin via a photolabile o-nitrobenzyl linker. Reduction of the azide by the Staudinger reaction to its corresponding amine followed by acylation using four activated NFmoc protected amino acids gave a first level of diversity. Subsequent deprotection of the Fmoc followed by a second acylation with five activated carboxylic acids produced, after photocleavage, a model library of twenty antiestrogen-related 7alpha-alkylamide estradiol derivatives in acceptable overall yields and very good purities.