The enantiomers of carbocyclic 5'-norguanosine: activity towards Epstein-Barr virus.
(-)-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 microg/mL), immunofluorescence assay for VCA or gp 350/250 (1.8-4.0 microg/mL) and DNA hybridization (EC50 0.82 microg/mL) assays with no accompanying toxicity seen in the host Daudi cells. No activity was noted for 4.
Rajappan
Vasanthakumar
V
Department of Chemistry, Auburn University, Auburn, AL 36849-5312, USA.
Schneller
Stewart W
SW
Williams
Stephanie L
SL
Kern
Earl R
ER
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D006151:Guanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D004854:Herpesvirus 4, Human / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014780:Viruses / Q000187:drug effects
D000998:Antiviral Agents; C464978:carbocyclic 5'-norguanosine; D006151:Guanosine