title: Stereoselective and improved syntheses and anticancer testing of 3'-O-silatranylthymidines.
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.
authors.affiliation: Xavier University, Chemistry Department, 3800 Victory Parkway, Cincinnati, OH 45207-4221, USA.
authors.forename: Christine A
authors.initials: CA
authors.lastname: Black
authors.forename: Jason W
authors.initials: JW
authors.lastname: Ucci
authors.forename: Jeremy S
authors.initials: JS
authors.lastname: Vorpagel
authors.forename: Matthew C
authors.initials: MC
authors.lastname: Mauck
authors.forename: Edward E
authors.initials: EE
authors.lastname: Fenlon
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001932:Brain Neoplasms / Q000188:drug therapy / Q000473:pathology; D001943:Breast Neoplasms / Q000188:drug therapy / Q000473:pathology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy / Q000473:pathology; D017646:Organosilicon Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D017646:Organosilicon Compounds; C015503:silatrane; D013936:Thymidine