Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives

Bioorg Med Chem. 2011 Mar 15;19(6):1860-5. doi: 10.1016/j.bmc.2011.02.007. Epub 2011 Mar 2.

Abstract

In this work, a new series of arysulfonylhydrazine-1H-1,2,3-triazole derivatives were synthesized, and their ability to inhibit the in vitro replication of HSV-1 was evaluated. Among the 1,2,3-triazole derivatives, 1-[(5″-methyl-1″-(4‴-fluorophenylamino)-1H-1,2,3-triazol-4″-yl)carbonyl]-2-(4'-methylphenylsulfonyl)hydrazine and 1-[(5'-methyl-1'-(2″,5″-dichlorophenylamino)-1H-1,2,3-triazol-4'-yl)carbonyl]-2-(phenylsulfonyl)hydrazine, with IC(50) values of 1.30 and 1.26 μM, respectively, displayed potent activity against HSV-1. Because these compounds have low cytotoxicity, their selectivity indices are high. Under the assay conditions, they have better performance than does the reference compound acyclovir. The structures of all of the compounds were confirmed by one- and two-dimensional NMR techniques ((1)H, (13)C-APT, COSY-(1)H×(1)H and HETCOR (1)J(CH)) and by elemental analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / toxicity
  • Chlorocebus aethiops
  • DNA Replication / drug effects
  • Herpesvirus 1, Human / drug effects*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / toxicity
  • Vero Cells

Substances

  • Antiviral Agents
  • Triazoles