| Abstract [eng] |
Reaction of 3-chloroaniline with itaconic acid provided 1-(3-chlorophenyl)-5oxopyrrolidine-3-carboxylic acid, which condensation reaction with o-phenylenediamine gave 4(1H-benzoimidazol-2-yl)-1-(3-chlorophenyl)pyrrolidin-2-one. Esterification of this compound with ethyl chloroacetate gave ethyl 2-{2-[1-(3-chlorophenyl)-5-oxopyrrolidin-3-yl]-1Hbenzoimidazol-1-yl}acetate. 2-{2-[1-(3-chlorophenyl)-5-oxopyrrolidin-3-yl]-1H-benzoimidazol1-yl}acetohydrazide was obtained by the reaction of ester with hydrazine hydrate. Synthesis reactions of hydrazide with butan-2-one, acetophenone, p-bromobenzaldehyde, 2hydroxybenzaldehyde, 5-bromo-2-thiophenecarboxaldehyde, 2-nitrobenzaldehyde were performed to synthesize corresponding acetohydrazides. Respective thiosemicarbazides were obtained by the hydrazide reactions with methylizothiocyanate and phenylisothiocyanate. 2-(2-{2[1-(3-chlorophenyl)-5-oxopyrrolidin-3-yl]-1H-benzoimidazol-1-yl}acetyl)-Nphenylhydrazinecarbothioamide were heated in 15 % solution of potassium hydroxide in order to get suitable 1,2,4-triazole. 1-(3-Chlorophenyl)-4-{1-[(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4triazol-3-yl)methyl]-1H-benzoimidazol-2-yl}pyrrolidin-2-one was used to synthesize corresponding 1,3,4-oxadiazole and S-alkylated compounds. The structures of synthesized compounds were confirmed by 1H NMR, 13C NMR, IR and mass spectroscopies. Biological activity of the synthesized compounds was studies by the method of laboratory monitoring. The results showed that 4-(1H-benzoimidazol-2-yl)-1-(3-chlorophenyl)pyrrolidin-2one had the best antioxidant activity properties while 2-(2-{2-[1-(3-chlorophenyl)-5oxopyrrolidin-3-yl]-1H-benzoimidazol-1-yl}acetyl)-N-phenylhydrazinecarbothioamide showed the best reduction properties. |
