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Synthesis and antitumour properties of 2-thio-5-chloro-nucleosides






Nucleosides & Nucleotides 14(3-5): 653-656

Synthesis and antitumour properties of 2-thio-5-chloro-nucleosides

Four methods are described for the synthesis of 2-thio-5-chlorouracil (1). beta- and alpha-5-Chloro-2-thio-2'-deoxyuridines (12 and 13) were obtained by Lewis acid catalysed condensation of TMS derivative of 1 with 2-deoxy-3,5-di-O-p-toluyl-alpha-D-ribosyl chloride and deblocking of toluylated derivatives with methanolic ammonia. Selective enzymatic phosphorylation of 12 led to its 5'-monophosphate, the latter being a moderate inhibitor of thymidylate synthase, while 12 showed moderate cytotoxicity in vitro against mouse leukemic cells L15178Y.

Accession: 009503983

DOI: 10.1080/15257779508012444

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