Synthesis and Antitumour Properties of 2-Thio-5-chloro-nucleosides |
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| Authors: | K Felczak M Bretner M Balińska J M Dzik W Rode T Kulikowski |
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| Institution: | 1. Institute of Biochemistry and Biophysics, Polish Academy of Sciences , 5a Pawińskiego St., 02-106, Warszawa, Poland;2. Nencki Institute of Experimental Biology, Polish Academy of Sciences , 3 Pasteur St., 02-093, Warszawa, Poland |
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| Abstract: | Abstract Four methods are described for the synthesis of 2-thio-5-chlorouracil (1). β- and α-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-α-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. |
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