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In this study, the anti-herpetic activities of novel 2′-methyl nucleoside analogues which were substituted at the 5 position of the pyrimidine with a halogen were investigated. The 2′-fluoro-5-iodo-aracytosine (FIAC) congeners (2′S)-2′-deoxy-2′- C-methylcytidine which were substituted with Br or I at the 5 position (SMBC or SMIC); and 2′-fluoro-5-iodo-arauridine (FIAU) congeners (2′S)-2′-deoxy-2′-C-methyluridine which were substituted with Br or I at the 5 position (SMBU or SMIU), proved to have potent antiviral activities against herpes simplex virus type-1 (HSV-1) and varicella-zoster virus (VZV) but not against herpes simplex virus type-2 (HSV-2). SMIU has a higher selective index against HSV-1 than FIAU, and both SMIC and SMIU showed higher inhibitory effects against VZV replication than aciclovir. The four effective compounds were not inhibitory to a thymidine kinase (TK)-negative HSV-1 strain, and this result indicates that phosphorylation of the compounds by HSV or VZV-TK is necessary for the activation of these compounds.

The FIAU Derivative (2′S)-2′-Deoxy-2′-C-Methyl-5-Iodouridine (SMIU) is a Novel, Less Cytotoxic and Potent anti-HSV and anti-VZV Agent