5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication.
2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.
Wigerinck
P
P
Rega Institute for Medical Research, Katholieke Universiteit Leuven, Belgium.
Pannecouque
C
C
Snoeck
R
R
Claes
P
P
De Clercq
E
E
Herdewijn
P
P
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001973:Bromodeoxyuridine / Q000031:analogs & derivatives* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014645:Herpesvirus 3, Human / Q000187:drug effects; D015394:Molecular Structure; D018139:Simplexvirus / Q000187:drug effects / Q000502:physiology*; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis / Q000494:pharmacology*; D014779:Virus Replication / Q000187:drug effects*
D000998:Antiviral Agents; D013876:Thiophenes; C070460:5-(5-bromothien-2-yl)-2'-deoxyuridine; C070461:5-(5-chlorothien-2-yl)-2'-deoxyuridine; C020235:brivudine; D001973:Bromodeoxyuridine; D003857:Deoxyuridine