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

[ Vol. 11 , Issue. 4 ]

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.

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.

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