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Current Organic Synthesis
ISSN (Print): 1570-1794
ISSN (Online): 1875-6271
VOLUME: 11
ISSUE: 4
DOI: 10.2174/15701794113106660078      Price:  $58









Synthesis of an Estradiol Derivative with an Adenosine-phosphate Mimic Linked at Position 16β

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Author(s): Amelie Talbot, Rene Maltais and Donald Poirier
Pages 612-620 (9)
Abstract:
We describe the synthesis and characterization of three compounds targeting the enzyme 17β-hydroxysteroid dehydrogenase type 1. The first one is a 4-aminobenzoyl-phenylacetic acid derivative designed as a mimic of adenosine-phosphate, the second one is an estradiol derivative having a decyl side chain at position 16β, and the third one is a hybrid compound with the adenosine-phosphate mimic covalently linked to the C16-estradiol side chain. Judicious use of key reactions such as Claisen rearrangement, microwave Grignard alkylation, selective TEMPO oxidation and cross metathesis has been required to achieve these targeted molecules.
Graphical Abstract:
Keywords:
Cofactor mimics, cross-metathesis reaction, enzyme substrate, estradiol derivative, hybrid inhibitor, steroid.
Affiliation:
Laboratory of Medicinal Chemistry, CHU de Quebec-Research Center and Laval University, 2705, Laurier Boulevard, Quebec, Quebec, G1V 4G2, Canada.