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

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 alpha-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 alpha-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. (C) 2013 Elsevier Masson SAS. All rights reserved.