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Synthesis and antimetabolic properties of 4,5-substituted pyrimidine 2'-deoxynucleosides and their 5'-monophosphates. 1987
T Kulikowski, and
M Bretner, and
J M Dzik, and
Z Zieliński, and
J Cieśla, and
W Rode, and
J A Vilpo, and
D Shugar
Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Warszawa.
Reaction of the reagent of Lawesson, 2,4-bis(p-methoxyphenyl)-1,3,4-dithiadiphosphatane-2,4-disulfide, with blocked uracil nucleosides in dioxane leads to quantitative thionation at C(4). With the bases, thionation occurs at C(4) and, with two equivalents of the reagent, at C(2) and C(4). Enzymatic phosphorylation of 4-thio-FdUrd gave the 5'-monophosphate, which was further converted with NH2OH to N4-hydroxy-FdCMP. Both nucleotides were examined as potential inhibitors of thymidylate synthase, and 4-thio-FdUrd for cytotoxic activities vs monkey and human leukemic cell lines.
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