Synthesis and antiviral activity of monofluoro and difluoro analogs of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1)

…, DJ Bushnell, IB Duncan, SJ Dunsdon…

Index: Martin; Bushnell; Duncan; Dunsdon; Hall; Machin; Merrett; Parkes; Roberts; Thomas; Galpin; Kinchington Journal of Medicinal Chemistry, 1990 , vol. 33, # 8 p. 2137 - 2145

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Citation Number: 91

Abstract

20 R= H the 3'-and 5'-hydroxyl groups are required for good substrate activity. While the 5'- hydroxyl group must be retained in order to allow phosphorylations to the 5'-triphosphate, the 3'-hydroxyl may be replaced by other functions which mimic that functional group. One of the most favored replacements in carbohydrates is a fluorine atom" which is strongly electronegative but sterically undemanding. Since fluorine has approximately the same ...