Synthesis and antiviral evaluation of carbocyclic analogs of ribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines

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Abstract
Carbocyclic analogs of ribofuranosides of 2-amino-6-substituted purines and of 2-amino-6-substituted 8-azapurines were prepared from the 2-amino-6-chloropurine ribofuranoside analog and the 2-amino-6-chloro-8-azapurine ribofuranoside analog, respectively. Analogs of purine ribofuranosides with the chloro, amino, methylamino or methylthio group at position 6, the thioguanosine analog, and the previously reported guanosine analog were evaluated in vitro against herpes simplex virus type 1 (HSV-1). 8-Azapurine ribofuranoside analogs with the chloro, amino or methylthio group at position 6 and the previously reported 8-azaguanosine analog were also evaluated against HSV-1. The carbocyclic analog of 2,6-diaminopurine ribofuranoside is highly active against HSV-1 and, also, against vaccinia virus. The 2-amino-6-chloropurine, 2-amino-6-(methylamino)purine and the 2,6-diamino-8-azapurine derivatives also demonstrated significant activity against HSV-1.