| Abstract [eng] |
In search of new synthetic biologically active compounds derivatives of azole bearing moiety are particurlarly important, because of their wide spectrum of activity. The purpose of this work is to synthesize various amides, substituted heterocyclic systems bearing azole moieties and to test their antimicrobial activity. 1-(4-Chlorophenyl)-5-oxopyrrolidine-3-carboxylic acid was used in synthesis of its methyl ester, amides and compounds bearing benzimidazole moiety. Acid hydrazide was obtained from ester and used in reaction with potassium thiocyanate to provide 1-(4-chlorophenyl)-4-(5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-one. Its chemical characteristics were investigated and S-alkylation reactions were performed with ethyl chloracetate and 2-bromacetophenones. Ethyl ((3-(1-(4-chlorophenyl)-5-oxopyrrolidin-3-yl)-1H-1,2,4-triazol-5-yl)sulfanyl)acetate was used to synthesize ((3-(1-(4-chlorophenyl)-5-oxopyrrolidin-3-yl)-1H-1,2,4-triazol-5-yl)sulfanyl)ethanehydrazide and 1-(4-chlorophenyl)-4-(5-((2-(4-substituted-phenyl)-2-oxoethyl)sulfanyl)-1H-1,2,4-triazol-3-yl)pyrrolidin-2-ones, which were condensed in acidic environment to provide corresponding thiazolotriazole derivatives. 4-((4-Chlorophenyl)amino)-3-(6-methyl-1H-benzimidazol-2-yl)butanoic acid was synthesized and in the presence of hydrazine hydrate transformed into 4-((4-chlorophenyl)amino)-3-(6-methyl-1H-benzimidazol-2-yl)butanehydrazide. Both synthesized hydrazides were used in chemical transformations with 2,5-hexanedione and aldehydes to provide corresponding compounds bearing pyrrole moiety and hydrazones. Part of the synthesized compounds were screened for antibacterial activity against Gram-positive Staphylococcus aureus, Listeria monocytogenes and Gram-negative Salmonella typhimurium, Pseudomonas aeruginosa ir Escherichia coli. Results showed that the highest antibacterial activity have compounds bearing pyrrole moieties, hydrazone with thiophen cycle and thiazolotriazole derivative. |
