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Stereoselective and improved syntheses and anticancer testing of 3'-O-silatranylthymidines
Christine A Black1, Jason W Ucci, Jeremy S Vorpagel
1Xavier University, Chemistry Department, 3800 Victory Parkway, Cincinnati, OH 45207-4221, USA.
Bioorganic & Medicinal Chemistry Letters
|November 22, 2002
Abstract:
A stereoselective synthesis of 3'-O-((R,R,R)-trimethylsilatranyl)thymidine (R,R,R-1) and synthesis of 3'-O-silatranylthymidine (5) via an improved silatranylation procedure using tetrakis(dimethylamino)silane are reported. Diastereomeric mixture 1 showed more activity than R,R,R-1 or 5 in a primary anticancer screen against breast, CNS, and lung cell lines; demonstrating the import of the configuration and presence, respectively, of the silatrane methyl groups for growth inhibition.