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Öğe Synthesis, characterization and antioxidant activity of heterocyclic Schiff bases(Journal of the Chinese Chemical Society, 2020-08-04) Aral, Tarık; Dağ, Beşir; Kızılkaya, Hakan; Genç, Nusret; Erenler, RamazanSchiff 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.Öğe HPLC separation of different groups of small polar compounds on a novel amide-embedded stationary phase(Elsevier, 2014-05-10) Aral, Hayriye; Aral, Tarık; Çelik, Kadir Serdar; Ziyadanoğulları, Berrin; Ziyadanoğulları, RecepRetention behaviors of an amide-embedded silica base stationary phase, which was recently developed by our group, were studied by using six different groups of small polar compounds including phenolic compounds, substituted anilines, chlorinated herbicides, Sudan dyes and some nucleotides and nucleosides in HPLC. The chromatographic behaviors of the prepared stationary phase for these analytes were compared with those of a commercially available reversed-phase column ACE C18 under same conditions. Among the six groups of analytes studied, the amide-silica stationary phase showed enhanced selectivity towards phenolic compounds, substituted anilines, Sudan dyes and herbicides under reversed-phase conditions and satisfactory selectivity towards nucleosides and nucleotides which could not be separated with ACE C18 column under HILIC conditions. Experimental data provided some evidence that functional groups on the stationary phases might have certain degrees of influence on selectivity possibly through secondary interactions with the model compounds. The retentions of the moderately polar compounds such as phenolic acids, anilines and herbicides on the stationary phase are higher than highly polar compounds such as nucleotides and nucleosides due to both the hydrophobic and hydrophilic interactions between the stationary phase and analytes. The quantitative determination of Sudan dyes (I, II, III, and IV) in red chilli peppers was performed. Many red chilli peppers were screened and three of them contained Sudans dyes.Öğe C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton nmr titration method(TÜBİTAK, 2013-07-08) Aral, Hayriye; Aral, Tarık; Çolak, Mehmet; Ziyadanoğulları, Berrin; Ziyadanoğulları, RecepTwo novel C2 -symmetric chiral diamines containing α-phenylethyl and α-(1-naphthyl)ethyl chiral subunits were prepared with quantitative yields. Enantiomeric recognition properties of these simple structured diamine ligands towards D- and L-amino acid esters and D- and L-mandelic acid were examined by the 1H NMR titration method. These ligands exhibited strong complexation (with Kf up to 2481 M-1) and good enantioselectivity (up to KL /KD = 4.08) towards the mandelic acid enantiomers. The results show that simple structured and easily accessible acyclic C2 -symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex molecules such as crown ethers and other cyclic molecules.
