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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 4-aminoantipirin türevi heterohalkalı yeni schiff bazlarının sentezi, karekterizasyonu ve antioksidan aktiviteleri(Batman Üniversitesi Fen Bilimleri Enstitüsü, 2019-08-26) Kızılkaya, Hakan; Dağ, BeşirBu çalışmada, üç tanesi yeni olmak üzere beş adet Schiff bazı sentezlendi. 4-(2-Piridilmetilen)amino-1-fenil-2,3-dimetil-5-pirazol-on (1) ve (4Z)-4-((tiofen-2-il)metilenamino)-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on (3), daha önce de sentezlenmiş olup, (E)-1,5-dimetil-4-((2-metil-1H-indol-3-il)metilenamino)-2-fenil-1H-pirazol-3(2H)-on (2), (4E)-4-((1H-indol-3-il)metilenamino)-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on (4) ve (E)-1,5-dimetil-2-fenil-4-(kinolin-2-il-metilenamino)-1H-pirazol-3(2H)-on (5) ise ilk kez sentezlendi. Sentezlenen bu Schiff bazlarının yapıları 1H NMR, 13C NMR ve FTIR ile aydınlatıldı. Sentezlenen bileşiklerin antioksidan aktiviteleri incelendi ve ABTS+• (2,2'-azino-bis(3-etilbenzotiyazolin-6-sülfonik asit)diamonyum katyonu) radikal katyonu giderme aktivitesi, DPPH• (1,1-difenil-2-pikrilhidrazil) radikal giderme aktivitesi ve indirgenme gücü aktivitesi yöntemleri kullanıldı. Trolox, BHT ve BHA standart olarak kullanıldı. Bileşik 1’in en yüksek antioksidan aktivite gösterdiği gözlendi.Öğe Synthesis characterization and using some of schiff base ligands derived from 4 aminoantipyrine as an inhibitor(Selçuk Üniversitesi, 2017) Dağ, Beşir; Yaşar, Fevzi; Kızılkaya, HakanSchiff bases and their complexes are widely studied because of the increasing recognition of their role in biological systems. In azo methine derivatives, the C=N linkage is essential for biological activity; several azomethines were reported to possess remarkable antibacterial and antifungal, anticancer. With the increasing incidence of deep mycosis, there has been increasing emphasis on the screening of new and more effective antimicrobial drugs with low toxicity. These compounds were recently found to have significant antitumor and biological activity. Antipyrine derivatives are reported to exhibit analgesic and antiinflammatory effects, antiviral, antibacterial, and herbicidal activities, and have also been used as hair color additives and to potentiate the local anesthetic effect of Lidocaine. Transition metal complexes with ligands derived from 4-aminoantipyrine have significant biological activity. This prompted us to synthesize a new series of heterocyclic Schiff bases containing the antipyrinyl moiety. The present study reports synthesis and charaterization of Schiff bases derived from 1-phenyl-2,3-dimethyl-4-(N-2 hydroxybenzylidene)-3- pyrazolin-5-one and 1-phenyl-2,3-dimethyl-4-(N-2-hydroxynaphthylidene)-3-pyrazolin-5- one with 5-aminoisophtlalic acid [1-2]. These compounds were synthesized in high yield and characterized by SEM, FT–IR, 1H NMR and 13C NMR.Öğe 4-aminoantipirin türevi heterohalkalı schıff bazlarının sentezi, karekterizasyonu ve antioksidan aktiviteleri(Batman Üniversitesi Fen Bilimleri Enstitüsü, 2019-08-26) Kızılkaya, Hakan; Dağ, BeşirBu çalışmada, 4-aminoantipin türevi beş adet Schiff bazı sentezlendi: 4-(2-Piridilmetilen)amino-1-fenil-2,3-dimetil-5-pirazol-on (1), (E)-1,5-dimetil-4-((2-metil-1H-indol-3-il)metilenamino)-2-fenil-1H-pirazol-3(2H)-on (2), (4Z)-4-((tiofen-2-il)metilenamino)-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on (3), (4E)-4-((1H-indol-3-il)metilenamino)-1,2-dihidro-2,3-dimetil-1-fenilpirazol-5-on (4) ve (E)-1,5-dimetil-2-fenil-4-(kinolin-2-il-metilenamino)-1H-pirazol-3(2H)-on (5). Sentezlenen bu Schiff bazlarının yapıları 1H NMR, 13C NMR ve FTIR ile aydınlatıldı. Sentezlenen bileşiklerin antioksidan aktiviteleri incelendi ve ABTS+• (2,2'-azino-bis(3-etilbenzotiyazolin-6-sülfonik asit)diamonyum katyonu) radikal katyonu giderme aktivitesi, DPPH• (1,1-difenil-2-pikrilhidrazil) radikal giderme aktivitesi ve indirgenme gücü aktivitesi yöntemleri kullanıldı. Trolox, BHT ve BHA standart olarak kullanıldı. Bileşik 1'in en yüksek antioksidan aktivite gösterdiği gözlendi.
