title: [Homoanalogues of pyrimidine nucleosides. XII. 3,6-anhydro-1,2-bis-desoxy-1-(pyrimidin- and 5-halopyrimidin-1-yl)-D-arabinohexitols; 3,6-anhydro-1-desoxy-1(5-halopyrimidin-1-yl)-D-glucitols].
abstract: Lithium aluminium hydride reduction of 3,6-anhydro-1-o-benzoyl-4,5-o-isopropylidene-2-o-p-tolylsulfonyl-D-mannitol (II) gives with 74% yield 3,6-anhydro-2-deoxy-4,5-o-isopropylidene-D-arabino-hexitol (III). This compound is used as its corresponding 1-o-p-toluene-sulfonate (IV) for the N-1 alkylation of uracil, 5-fluorouracil, thymine and N-acetylcytosine. Acidic cleavage of the acetal protecting group gives the expected bis-homoanalogues of the pyrimidine- and halopyrimidine-nucleosides (V-VIII) which are characterized mainly through their mass spectra and U.V. absorption. 3,6-Anhydro-1,2-dideoxy-1-(5-bromo- and 5-iodouracil-1-yl)-D-arabino-hexitols (XIII, XIV), 3,6-anhydro-1-deoxy-1-(5-bromo- and 5-iodouracil-1-yl)-D-glucitols (XV, XVI) are similarly prepared by direct halogenation of the corresponding uracil derivatives. Results of cytotoxic, cytostatic and antiviral tests are described.
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D006564:Herpesviridae / Q000187:drug effects; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D010084:Oxidation-Reduction; D010224:Parainfluenza Virus 3, Human / Q000187:drug effects; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013402:Sugar Alcohols / Q000138:chemical synthesis
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides; D013402:Sugar Alcohols
vernacular_title: Homoanalogues des nucléosides pyrimidiques. XII - 3,6-anhydro-1,2-bis-désoxy-1-(pyrimidin- et 5-halopyrimidin-1-yl)-D-arabino-hexitols; 3,6-anhydro-1-désoxy-1-(5-halopyrimidin-1-yl)-D-glucitols.