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  • 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].
    Author: Cavrini V, Garuti L, Giovanninetti G, Amorosa M, Mannini Palenzona A, Defaye J.
    Journal: Farmaco Sci; 1979 Jul; 34(7):635-45. PubMed ID: 225200.
    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.
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