Stereoselective and improved syntheses and anticancer testing of 3'-O-silatranylthymidines |
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Authors: | Black Christine A Ucci Jason W Vorpagel Jeremy S Mauck Matthew C Fenlon Edward E |
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Affiliation: | Xavier University, Chemistry Department, 3800 Victory Parkway, Cincinnati, OH 45207-4221, USA |
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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. |
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