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Nucleic Acids Research, 1975, Vol. 2, No. 4 487-499
© 1975

Articles

Synthesis and spectxoscopic properties of two classes of 5,6-dihydrothymidine derivatives. Action on the Ehrlich's ascites cells thymidine kinase

Robert Teoule, Brigitte Fouque and Jean Cadet

Laboratoire de Radiobiologie, Department de Recherche Fondamentale, Centre d'Etudes Nucleaires BP 85, Centre de Tri, 38041 Grenoble Cedex, France

Received January 2, 1975. Trans (+) and (–) 6-alkoxy-5-bromo-5,6 dihydrothymidine and trans (+) and (–) 6-alkoyloxy-5-bromo-5,6-dihydrothymidine compounds have been prepared. The synthesis of these substances (alkoxy : methoxy, ethoxy, butyloxy and isoamyloxy and alkoyloxy : acetoxy and bensoyloxy) is described. Diastereoisomcrs of all products have been isolated by thin layer chromatography and their spectroscopic properties (IR, UV, NMR, mass spectrometry) studied. These compounds have been shown to be competitive inhibitors of Ehrlich's ascites cells thymidine kinase with respect to thymidine.


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