FABAD JOURNAL OF PHARMACEUTICAL SCIENCES, vol.48, no.3, pp.459-468, 2023 (Scopus)
In this study, 5 new Schiff base compounds containing triazole-imidazole rings were synthesized. Compounds containing this binary system have been realized for heterocyclic imine derivative compounds. According to literature information, these obtained compounds are expected to have potential biological activities such as anticonvulsant and antimicrobial activities. In the first step of the synthesis, iminoster derivative compounds (1a-e) were obtained from aryl/alkyl nitrile compounds by the Pinner method. In the second step, ester ethoxycarbonyl derivative compounds (2a-e) were obtained by the reaction of aryl/alkyl iminoester (1a-e) compounds with ethoxycarbonyl hydrazine compound. The resulting ester ethoxycarbonyl hydrazones were reacted with hydrazine hydrate, and the corresponding triazole-amine (3a-e) compounds were obtained using the method given in the literature. In the original step of the study, the 5-substituted-4-amino-1,2,4-triazol-3-one compounds (3a-e) were reacted with 4-imidazole carboxyaldehyde and five new Schiff bases 4-{[((1H-imidazol-4-yl)methylene]amino}-5-substituted-2,4-dihydro3H-1,2,4-triazole-3-one compounds (4a-e) were obtained. A series of 5 new 5-substituted-4-{[(1H-imidazol-4-yl)methylene]amino}2,4-dihydro-3H-1,2,4-triazole-3-one (4a-e) were synthesized, and their physical properties and IR, 1H-NMR, and 13C-NMR spectral analyses were performed to elucidate the structures of the compounds. The pancreatic lipase enzyme inhibition activities of the obtained new Schiff base compounds were investigated. They showed average activity against the positive control “Orlistat”.