Synthesis and antiviral activity of phthiobuzone analogues

Chem Pharm Bull (Tokyo). 2010 Feb;58(2):208-11. doi: 10.1248/cpb.58.208.

Abstract

A series of phthiobuzone analogs, prepared from potassium phthalimide or phthalandione, have been evaluated for their antiviral activities. Among the candidates, compounds 5j and 5k, which contain the substituted 4-halogenated phenyl ring at N-4',4'' position, show more potent antiviral activity than phthiobuzone against herpes simplex virus 1 (IC(50)=8.56 and 2.85 microg/ml, respectively) and herpes simplex virus 2 (IC(50)=1.75 and 4.11 microg/ml, respectively). Compounds 9c and 9d with a propylene linker between the phthalimide and bisthiosemicarbazone moieties display similar antiviral potency against herpes simplex virus 1 (IC(50)=2.85 and 4.11 microg/ml, respectively).

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Chlorocebus aethiops
  • Herpes Simplex / drug therapy*
  • Herpesvirus 1, Human / drug effects*
  • Herpesvirus 2, Human / drug effects*
  • Molecular Structure
  • Phthalimides / chemical synthesis
  • Phthalimides / chemistry*
  • Phthalimides / pharmacology*
  • Structure-Activity Relationship
  • Thiosemicarbazones / chemical synthesis
  • Thiosemicarbazones / chemistry*
  • Thiosemicarbazones / pharmacology*
  • Vero Cells

Substances

  • Antiviral Agents
  • Phthalimides
  • Thiosemicarbazones
  • phtiobuzone