Synthesis, antiretrovirus effects and phosphorylation kinetics of 3'-isocyano-3'-deoxythymidine and 3'-isocyano-2', 3'-dideoxyuridine

…, E Zbiral, J Balzarini, E De Clercq

Index: Hiebl, Johann; Zbiral, Erich; Balzarini, Jan; Clercq, Erik De Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 845 - 848

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Citation Number: 26

Abstract

The silylated AzddThd 5 and AzddUrd 6 prepared from 2, 3'-anhydronucleoside derivatives 3 and 4 were transformed to formamides 7 and 8 by using the sequence RN3-RN= P (C6H5)- RNHCHO. Formamides 7 and 8 were dehydrated to the protected 3'4socyano derivatives 9 and 10; deblocking gave 11 and 12. Neither 3'4socyano-3'-deoxythymidine (1 1) nor 3'- isocyano-2', 3'-dideoxyuridine (12) showed anti-HIV activity at noncytotoxic concentrations ...