| Abstract [eng] |
Nowadays, one of the biggest challenges for medicinal chemists is the discovery of new antimicrobial agents. Because people have to control the increasing number of drug-resistant microbial strains. Various hydrazone derivatives can act as potential anticancer, antimicrobial agents. In addition, the pharmacological effects are related to antioxidant, analgesic, anti-inflammatory, antiviral, anticonvulsant and antimalarial effects. They can be synthesized in organic solvents with or without acid additives. Hydrazones are mostly crystalline, readily available organic compounds. According to the data found in the literature, the bioactivity of hydrazones increases with the appearance of functional groups such as hydroxy, methoxy, nitro, amino, etc. in the structure. Condensation reactions of hydrazones with aromatic aldehydes and ketones were performed in this work. During the research, N'-substituted hydrazone derivatives were obtained from 3-[(4- mehylphenyl)amino]propanehydrazide (3-(p-tolylamino)propanehydrazide). 2-{3-[(4- methylphenyl)amino]propanoyl}-N-phenylhydrazinecarbothioamide was then synthesized from this main compound in a reaction using phenylisothiocyanate as a reagent. This compound was synthesized to undergo acidic cyclization with conc. H2SO4 and give the thiadiazole – 5-{2-[(4- methylphenyl)amino]ethyl}-N-phenyl-1,3,4-thiadiazol-2-amine. Several different reaction conditions for N-alkylation of thiadiazole have been found in the literature, so they were tested in this work. The antioxidant and antibacterial activities of the newly obtained compounds against several bacterial strains were tested in biological assays. It was found that N’-[1-(furan-2-yl)ethyldene]-3-(ptolylamino)propanehydrazide, N’-(1-(thiophen-2-yl)ethyldene)-3-(p-tolylamino)propanehydrazide and N’-[1-(3-aminophenyl)ethyldene]-3-(p-tolylamino)propanehydrazide had the highest antioxidant activity. N’-(furan-2-ylmethylene)-3-(p-tolylamino)propanehydrazide showed the highest antibacterial activity against gram-negative bacteria E. coli, N’-(1-phenylpropyldene)-3-(ptolylamino)propanehydrazide – X. campestris, N’-(4-nitrophenylidene)-3-(ptolylamino)propanehydrazide for R. radiobacter, and N’-[1-(furan-2-yl)ethyldene]-3-(ptolylamino)propanehydrazide against Gram-positive B. subtilis. |
