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Revista de Chimie (Rev. Chim.), Year 2010, Volume 61, Issue 10,





Constantin TAnase, Florea G.Cocu, Miron Teodor Caproiu, Constantin Draghici, Ionela Victoria Neagoe, Cristian Enache, Sultana Nita
Novel O2-Nucleoside Analogues with an Optically Active Bicyclo<2.2.1>Heptane Sugar Moiety, Obtained by Mitsunobu Reaction

Abstract:

Novel O2-pyrimidine nucleosides with a functionalized bicyclo[2.2.1]heptan sugar moiety were synthesized starting from a pure optically active alcohol (4). This alcohol was coupled by Mitsunobu reaction to pyrimidine bases: N4-benzoylcytosine, 5-fluorouracil and N3-benzoyl-thymine, then the ester protected nucleosides were debenzoylated to the coresponding carbocyclic nucleosides, which looks to be O2-linked compounds. The compounds were characterized by IR, MS, 1H-NMR and 13C-NMR spectra. The preliminary in vitro preclinical results show that ent-27-5-FU (13) and ent-27-T (19) present cytotoxic or cytototxic activity in Jurkat lymphoblasts and/or U937 monocytic blasts. Keywords: Mitsunobu synthesis, bicyclo[2.2.1]heptane nucleoside, carbocyclic nucleoside, anti-neoplastic activity


Issue: 2010, Volume 61, Issue 10
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