Synthesis, characterization and antioxidant activity of heterocyclic Schiff bases
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CitationAral T., Dağ, B., Kızılkaya, H., Genç, N. ve Erenler, R. (2020). Synthesis, characterization and antioxidant activity of heterocyclic Schiff bases. Journal of the Chinese Chemical Society, 67 (9), 99. 1696–1701. https://dx.doi.org/10.1002/jccs.202000161
Schiff base derivatives have gained great importance due to revealing a great number of biological properties. Schiff bases were synthesized by treatment of 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (1) with various aldehydes in methanol at reflux. In addition, diamine was reacted with an aldehyde to yield the corresponding Schiff bases. The structures of synthesized Schiff bases were elucidated by spectroscopic methods such as microanalysis, 1 H-NMR, 13C-NMR, and FTIR. Antioxidant activities of synthesized Schiff bases were carried out using different antioxidant assays such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH• ) scavenging, 2,20 -azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, and reducing power activity. (E)-4-((1H-indol-3-yl)methyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (3), (E)-1,5-dimethyl-4-((2-methyl-1H-indol-3-yl) methyleneamino)-2-phenyl-1H-pyrazol-3(2H)-one (5), (E)-1,5-dimethyl-2-phenyl-4-(thiophen-2-ylmethyleneamino)-1H-pyrazol-3(2H)-one (7), (E)-1,5-dimethyl2-phenyl-4-(quinolin-2-ylmethyleneamino)-1H-pyrazol-3(2H)-one (9), (1S,2S, N1,N2)-N1,N2-bis((1H-indol-3-yl)methylene)cyclohexane-1,2-diamine (11), and (1S,2S,N1,N2)-N1,N2-bis((2-methyl-1H-indol-3-yl)methylene)cyclohexane-1,2-diamine (12) were synthesized in high yields. Compound 5 displayed a good ABTS•+ activity. Compound 3 revealed the outstanding activity in all assays. Compound 7 has the best-reducing power ability in comparison to other synthesized compounds. Although compounds 5, 11, 12 are new, compounds 3, 7, 9 are known. Due to revealing a good antioxidant activity, the synthesized compounds (3, 5, 7) have the potential to be used as synthetic antioxidant agents.
SourceJournal of the Chinese Chemical Society
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