Synthesis, configurational stability and stereochemical biological evaluations of (S)- and (R)-5-hydroxythalidomides
2009
Abstract The first asymmetric synthesis of ( S )- and ( R )-5-hydroxythalidomides, one of thalidomide’s major metabolites, was achieved using HMDS/ZnBr 2 -induced imidation as a key reaction. 5-Hydroxythalidomide was found to be configurationally more stable than thalidomide at physiological pH. Stereochemical biological effects of thalidomide and 5-hydroxythalidomide on anti-angiogenesis and antitumor activities were also investigated using racemic and pure enantiomers.
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