Synthesis and biological evaluation of some novel thiazole compounds as potential anti-inflammatory agents

Eur J Med Chem. 2013 Jul:65:517-26. doi: 10.1016/j.ejmech.2013.04.005. Epub 2013 Apr 30.

Abstract

In the present investigation, furo[2,3-d]thiazol-5(2H)-one 5 was obtained from reaction of thiosemicarbazone derivative 2 with diethyl acetylene dicarboxylate. A series of newly synthesized 2-(hydrazinyl)thiazol-4(5H)-one 6, 7 &8 and 2-(4-(substituted)-thiazol-2-yl)hydrazono derivatives 9a, b &10 were synthesized from treatment of thiosemicarbazone derivative 2 with appropriate α-halogenated compounds. Also, a one pot synthesis of thiazole derivatives 13 &15 was achieved from three components reaction of hydrazone derivative 11 with phenyl isothiocyanate and α-halogenated compounds catalyzed by DMF/KOH. 4-(4-Morpholino phenyl) thiazol-2-amino 17 was obtained via the reaction of acetophenone derivative 1 with thiourea in presence of iodine. The reactivity of 2-aminothiazole 17 toward some electrophilic reagents was investigated. The structure of the newly compounds was confirmed on the basis of elemental analysis and spectral data. The antibacterial activity towards two Gram negative (Proteus mirabilis &Serratia marcesens) and two Gram positive (Staphylococcus aureus &Bacillus cereus) bacteria was investigated. The anti-inflammatory activity was also investigated and the inhibition of the carrageenin-induced oedema by these compounds was established.

Keywords: Anti-inflammatory activity; Antibacterial; Furo[2,3-d]thiazole; Thiazole; Thiosemecarbazone.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Bacillus cereus / drug effects
  • Carrageenan
  • Dose-Response Relationship, Drug
  • Edema / chemically induced
  • Edema / drug therapy*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Proteus mirabilis / drug effects
  • Rats
  • Rats, Wistar
  • Serratia / drug effects
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Thiazoles
  • Carrageenan