| Abstract [eng] |
A series of new potentially biologically active 2,5-disubstituted thiazole derivatives, that have: benzene and various azole rings as well as hidrazone fragments in their structure were synthesized. Firstly, a pyrrolidone ring containing compound – 1-[4-(bromacetyl)phenyl)-5-oxopyrrolidin-3-carboxylic acid was transformed into a 1-[4-(2-phenyl-1,3-thiazol-5-yl)phenyl]-5-oxopyrrolidine-3-carboxylic acid by reaction with thiobenzamide. Then methyl carboxylate of earlier mentioned carboxylic acid was formed in order to obtain 1-[4-(2-phenyl-1,3-thiazol-5-yl)phenyl]-5-oxopyrrolidone-3-carbohydrazide which easily reacts with aromatic and heterocyclic aldehydes giving appropriate hydrazones. 3-Carbohydrazide also reacts with 2,5-hexanedione and 2,4-pentanedione, giving 2,5-dimethylpyrrole and 3,5-dimethylpyrazole derivatives. Oxadiazole-2-thione and triazole-3-thione derivatives were synthesized from 5-oxopyrrolidone-3-carbohydrazide by multi-step reactions with CS2 and phenyl isothiocianate. Biological evaluation of some synthesized compounds was performed using broth dilution and spread plate methods. Some of the new compounds posses very high antibacterial activity. The structure of synthesized compounds was confirmed by 1H, 13C NMR, MS, IR spectroscopy and elemental analysis data. |
