NEW 3′-DEOXYTHYMIDINES BEARING A NUCLEOPHILIC 3′-SUBSTITUENT

Abstract

New potential cancer-driven as well as HIV-driven nucleoside hetero- analogs, such as 3′-thio- and 3′- as well as 5′-selenosubstituted thymidines, have been synthesized. We also report an effective method for the preparation of novel nucleoside derivatives, bis(deoxynucleoside) diselenides, in nearly quantitative yields. The North conformation is significantly populated in the conformational equilibrium for 3′-α-alkylthiothymidines.

ACKNOWLEDGMENTS

We are grateful for support of this research by the Israel Ministry of Science and Technology (Grant 1471-1-99), the governmental KAMEA Program, and the Marcus Center for Pharmaceutical and Medicinal Chemistry. We thank Dr. J. G. Hengstler, University of Mainz, for bioassays on nucleoside 6b.

Notes

^*Recently we proposed deoxynucleoside selenocyanates as masked selenol deoxynucleosides.