Stereoselective and improved syntheses and anticancer testing of 3'-O-silatranylthymidines.
Black CA, Ucci JW, Vorpagel JS, Mauck MC, Fenlon EE.
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.