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

J Med Chem. 1991 Aug;34(8):2383-9. doi: 10.1021/jm00112a011.

Abstract

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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / pharmacology*
  • Bromodeoxyuridine / analogs & derivatives*
  • Bromodeoxyuridine / pharmacology
  • Chemical Phenomena
  • Chemistry
  • Deoxyuridine / analogs & derivatives*
  • Deoxyuridine / chemical synthesis
  • Deoxyuridine / pharmacology
  • Herpesvirus 3, Human / drug effects
  • Molecular Structure
  • Simplexvirus / drug effects
  • Simplexvirus / physiology*
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis
  • Thiophenes / pharmacology*
  • Virus Replication / drug effects*

Substances

  • Antiviral Agents
  • Thiophenes
  • 5-(5-bromothien-2-yl)-2'-deoxyuridine
  • 5-(5-chlorothien-2-yl)-2'-deoxyuridine
  • brivudine
  • Bromodeoxyuridine
  • Deoxyuridine