| Abstract [eng] |
This work involved performing reactions of 3-[(4-methyl-3-nitrophenyl)amino]propane hydrazide with several different organic reagents with the goal of producing its various compounds. To get the hydrazide, 4-methyl-3-nitroaniline was reacted with acrylic acid, the resulting carboxylic acid was esterified, and the ester was treated with hydrazine monohydrate. After obtaining the hydrazide, it was used in reactions with 2,4-pentanedione, 2,5-hexanedione, acetone, carbon disulfide, malonic anhydride and maleic anhydride, resulting in compounds with different moieties. The compounds were confirmed by 1H NMR, 13C NMR, mass spectrometer and elemental analysis data. Derivatives of the hydrazide as well as its synthesis intermediates were analyzed for their biological activity. Tests were done to determine the compounds’ anti-oxidative, reductive and DPPH, ABTS radical inhibitive properties, hydrogen peroxide scavenging as well as deoxyribose hydroxyl radical protection effectiveness. In addition, antimicrobial and barley seedling growth stimulation properties of select compounds were tested as well. The three compounds that showed the best antioxidative properties were chosen for in vitro barley seed growth regulation testing. 3-[(4-Methyl-3-nitrophenyl)amino]propanehydrazide stimulated barley growth the most, N-(2,5-dimethyl-1H-pyrrol-1-yl)-3-[(4-methyl-3nitrophenyl)amino]propanamide had the biggest effect on barley pigment amount and 5-{2-[(4methyl-3-nitrophenyl)amino]ethyl}-1,3,4-oxadiazole-2(3H)-thione showed the greatest effect on the sprouts’ antioxidative properties. Methyl-3-[(4-methyl-3-nitrophenyl)amino]propanoate, 3(2-{3-[(4-methyl-3-nitrophenyl)amino]propanoyl}hidrazinyl)propanoic acid and N-(2,5dioxypyrrolidin-1-yl)-3-[(4-methyl-3-nitropheyl)amino]propanamide showed antimicrobial activity against E. coli. N-(2,5-dimethyl-1H-pyrrol-1-yl)-3-[(4-methyl-3nitrophenyl)amino]propanamide exhibited good results in many of the biological activity tests and was selected for further production. A principal technological production line of the compound was created, and the main reaction properties were calculated. |
