title: Synthesis, molecular conformation and activity against herpes simplex virus of (E)-5-(2-bromovinyl)-2'-deoxycytidine analogs.
abstract: 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.
authors.affiliation: Department of Chemistry, Sultan Qaboos University, Al-Khod, Oman. zoghaibw@squ.edu.om
authors.forename: Wajdi Michel
authors.initials: WM
authors.lastname: Zoghaib
authors.forename: Shajan
authors.initials: S
authors.lastname: Mannala
authors.forename: V Sagar
authors.initials: VS
authors.lastname: Gupta
authors.forename: Guy
authors.initials: G
authors.lastname: Tourigny
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001972:Bromodeoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002460:Cell Line; D004355:Drug Stability; D006801:Humans; D008826:Microbial Sensitivity Tests; D018139:Simplexvirus / Q000187:drug effects*; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D001972:Bromodeoxycytidine; C045536:5-(2-bromovinyl)-2'-deoxycytidine