Nucleosides. 102. Synthesis of some 3'-deoxy-3'-substituted arabinofuranosylpyrimidine nucleosides.
The synthesis of some 3'-deoxy-3'-substituted arabinofuranosylcytosine (4a-d) and uracil (7a-d, 8a-d, X =Br, I, N3, SCN) nucleosides was accomplished by treatment of the requisite 2',3'-anhydrolyxofuranosylpyrimidine nucleoside (5,6a,b) with the appropriate ammonium salt in refluxing ethanol. Cleavage of the oxirane ring provided the desired 3'-deoxy-3'-substituted pyrimidine nucleosides (4a-d, 7a-d, and 8a-d). In vitro screening of compounds 4a-d, and 7a-d, with L5178Y cells in culture showed no significant inhibitory properties.
D002478:Cells, Cultured; D003561:Cytarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D004353:Drug Evaluation, Preclinical; D009374:Neoplasms, Experimental / Q000188:drug therapy; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*
D003853:Deoxyribonucleosides; D011741:Pyrimidine Nucleosides; D003561:Cytarabine