[Synthesis of potential antimetabolites in a series of carbohydrate-modified pyrimidine 2'-deoxynucleosides]

The interaction of 3'-amino-2',3'-dideoxy- or 5'-amino-2',5'-dideoxy-5-substituted pyrimidine nucleosides with N-ethylmaleimide in DMF in the presence of Et3N gave two diastereomeric 2',3'-dideoxy-3'-(N-ethylsuccinimido)- or 2',5'-dideoxy-5'-(N-ethylsuccinimido)aminonucleosides in each reaction. For 3'-amino-5-trimethylsilyl- and 3'-amino-5-benzyloxymethyl-2',5'-dideoxyuridine diastereomeric 3'-(N-ethylsuccinimido)derivatives were separated by preparative TLC. Structures of synthesized analogs were confirmed by UV-, IR- and 1H-NMR spectra. It has been shown that modified nucleosides at 10(-5)-10(-4) M concentrations do not inhibit the thymidine incorporation into DNA of CaOv cells in vitro.