SYNTHESIS OF POTENTIAL ANTIMETABOLITES IN THE SERIES OF SUGAR 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 th e presence of Et(3)N gave two diastereomeric 2',3'-dideoxy-3'-(N-ethyl succinimido)- or 5'-dideoxy-5'-(N-ethylsuccinimido)aminonucleosides in each reaction. For 3'-amino-5-trimethylsilyl- and 3'-amino-5-benzylox ymethyl-2',5'-dideoxyuridine diastereomeric 3'-(N-ethylsuccinimido)der ivatives were separated by preparative TLC. Structures of synthesized analogs were confirmed by UV-, IR- and H-1-NMR spectra. It has been sh own that modified nucleosides at 10(-5)-10(-4) M concentrations do not inhibit the thymidine incorporation into DNA of CaOv cells in vitro.