Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2'-deoxycytidine analogs.

Analogs of (E)-5-(2-bromovinyl)-2'-deoxycytidine (BrVdCyd) (1) by substitution at N-4 were synthesized to impart resistance against deamination. The anti-HSV-1 activity and solution conformation of these analogs were determined. N-4-Acetyl-BrVdCyd (2) was a potent inhibitor of HSV-1 replication whereas N-4-propanoyl-BrVdCyd (3) had good activity and N-4-Butanoyl-BrVdCyd (4) had only low activity against HSV-1 replication. N-4-Methyl-BrVdCyd (5) was devoid of activity against HSV-1.