Antiviral activity of benzotriazole derivatives. 5-[4-(Benzotriazol-2-yl)phenoxy]-2,2-dimethylpentanoic acids potently and selectively inhibit Coxsackie Virus B5

Bioorg Med Chem. 2015 Nov 1;23(21):7024-34. doi: 10.1016/j.bmc.2015.09.035. Epub 2015 Sep 25.

Abstract

A library of 64 benzotriazole derivatives (17 of which were [4-(benzotriazol-2-yl)phenoxy]alkanoic acids) were screened for antiviral activity against a panel of twelve DNA and RNA viruses. Twenty-six compounds (12 of which were [4-(benzotriazol-2-yl)phenoxy]alkanoic acids) displayed activity against one or more viruses. CVB-5, RSV, BVDV, Sb-1 and YFV were, in decreasing order, the more frequently and effectively affected viruses; DENV-2, WNV, HIV-1 and Reo-1 were only occasionally and modestly affected, while the remaining viruses were not affected by any of the tested compounds. Worth of note were compounds 33 and 35; the former for the activity against Sb-1 (EC50=7 μM) and the latter for the large spectrum of activity including six viruses with a mean EC50=12 μM. Even more interesting were the alkanoic acids 45-48 and 50-57 for their activity against RSV and/or CVB-5. In particular, compound 56 displayed a potent and selective activity against CVB-5 with EC50=0.15 μM and SI=100, thus representing a valuable hit compound for the development of antiviral agents for the treatment of human pathologies related to this virus.

Keywords: Anti-Flaviviridae agents; Antiviral agents; Coxsackie Virus B5 inhibitors; N-Substituted benzotriazoles; RSV inhibitors.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Cricetinae
  • DNA Viruses / drug effects
  • DNA Viruses / physiology
  • Dogs
  • Enterovirus B, Human / drug effects
  • Enterovirus B, Human / physiology*
  • Humans
  • RNA Viruses / drug effects
  • RNA Viruses / physiology
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / toxicity
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Triazoles
  • benzotriazole