Synthesis and antiviral evaluation of carbocyclic analogues of ribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
Carbocyclic analogues 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 analogue (2) and the 2-amino-6-chloro-8- azapurine ribofuranoside analogue (9), respectively. Analogues of purine ribofuranosides with the chloro, amino, methylamino, or methylthio group at position 6, the thioguanosine analogue, and the previously reported guanosine analogue were evaluated in vitro against herpes simplex virus, type 1 (HSV-1). 8- Azapurine ribofuranoside analogues with the chloro, amino, or methylthio group at position 6 and the previously reported 8- azaguanosine analogue were also evaluated against HSV-1. The carbocyclic analogue (6) 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.
D000241:Adenosine / Q000031:analogs & derivatives / Q000627:therapeutic use / Q000633:toxicity; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D004353:Drug Evaluation, Preclinical; D007202:Indicators and Reagents; D007939:Leukemia L1210 / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D011684:Purine Nucleosides / Q000627:therapeutic use* / Q000633:toxicity; D018139:Simplexvirus / Q000187:drug effects; D013053:Spectrophotometry; D013329:Structure-Activity Relationship; D014616:Vaccinia virus / Q000187:drug effects
D000998:Antiviral Agents; D007202:Indicators and Reagents; D011684:Purine Nucleosides; D000241:Adenosine