Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulfonamide and its derivatives

Eur J Pharm Sci. 2001 Dec;14(4):313-6. doi: 10.1016/s0928-0987(01)00197-x.

Abstract

4-[(1,2-Dihydro-2-oxo-3H-indol-3-ylidene) amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulphonamide and its derivatives were synthesized by reaction of isatin and its derivatives with sulphadimidine. Their chemical structures have been confirmed by IR, (1)H NMR data and elemental analysis. Investigation of anti-HIV activity of compounds were tested against replication of HIV-1 (IIIB) and HIV-2 (ROD) strains in acutely infected MT-4 cells and the activity compared with standard azidothymidine. Among the compounds tested, 4-[(1,2-dihydro-2 oxo-3H-indol-3-ylidene)amino]-N(4,6-dimethyl-2-pyrimidinyl)-benzene sulphonamide and its N-acetyl derivative were the most active compounds.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / pharmacology*
  • Benzenesulfonamides
  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / pharmacology
  • Cell Line
  • HIV-1 / drug effects
  • HIV-2 / drug effects
  • Humans
  • Isatin / analogs & derivatives
  • Isatin / chemical synthesis*
  • Isatin / pharmacology*
  • Sulfamethazine / analogs & derivatives
  • Sulfamethazine / chemical synthesis*
  • Sulfamethazine / pharmacology*
  • Sulfonamides / chemical synthesis
  • Sulfonamides / pharmacology
  • Zidovudine / chemistry
  • Zidovudine / pharmacology

Substances

  • Anti-HIV Agents
  • Carbonic Anhydrase Inhibitors
  • Sulfonamides
  • Sulfamethazine
  • Zidovudine
  • Isatin