The Enantiomers of Carbocyclic 5′-Norguanosine: Activity towards Epstein–Barr Virus

Abstract

(−)-5′-Noraristeromycin (1) has shown antiviral activity towards, particularly cytomegalovirus, vaccinia virus and measles while its (+)-enantiomer (2) is effective towards hepatitis B virus. To determine if the antiviral characteristics of 1 and 2 extended to the guanine analogues (3 and 4), these enantiomers were prepared and evaluated against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), cytomegalovirus (CMV), varicella zoster virus (VZV), Epstein–Barr virus (EBV), human herpes virus type 6 (HHV-6), human herpes virus type 8 (HHV-8), vaccinia virus (VV), cowpox virus (CV), vesicular stomatitis virus (VSV), respiratory syncytial virus (RSV), hepatitis B virus (HBV), and human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2). The only activity found for 3 was for Epstein–Barr virus in VCA Elisa (EC50 0.78 μg/mL), immunofluorescence assay for VCA or gp 350/250 (1.8–4.0 μg/mL) and DNA hybridization (EC50 0.82 μg/mL) assays with no accompanying toxicity seen in the host Daudi cells. No activity was noted for 4.