[Homoanalogs of aldofuranosylnucleosides. XI. 3,6-Anhydro-1-deoxy-1-(5-halogenouracil-1-yl)-D-mannitol].
3,6-Anhydro-1-deoxy-1-(5-bromouracil-1-yl)-D-mannitol (II) and 3,6-anhydro-1-deoxy-1-(5-iodouracil-1-yl)-D-mannitol (III) were prepared by direct halogenation of the corresponding bis-homonucleosides; the 5-fluoro isomer (V) was prepared by N-alkylation of 5-fluorouracil by 2-o-acetyl-3,6-anhydro-4,5-o-isopropylidene-1-o-p-tolysulfonyl-D-mannitol in dimethylsulfoxide in the presence of potassium carbonate followed by hydrolysis of the protective groups in an acid medium. The ultraviolet spectroscopy, mass spectrometry and nuclear magnetic resonance studies of these compounds are described and the results of pharmacological tests on L 1210 leukemic cells are given.
D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001973:Bromodeoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006801:Humans; D006868:Hydrolysis; D007065:Idoxuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008353:Mannitol / Q000031:analogs & derivatives / Q000138:chemical synthesis; D013058:Mass Spectrometry
D000970:Antineoplastic Agents; D008353:Mannitol; D001973:Bromodeoxyuridine; D007065:Idoxuridine
Homoanalogues des aldofuranosylnucleosides. XI. 3,6-Anhydro-1-désoxy-1-(5-halogénouracil-1-yl)-d-mannitols