Browsing by Author "Okumus, Veysi"

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Design of Novel Binuclear Phthalocyanines Formed by Dioxyphenyl Bridges: Synthesis and Investigation of Thermal and Antioxidant Properties
(Wiley-v C H verlag Gmbh, 2012) Agirtas, M. Salih; Gumus, Ilkay; Okumus, Veysi; Dundar, Abdurrahman
4, 4'-(1, 4-Phenylenebis(oxy)diphthalonitrile was synthesized by reaction of hydroquinone with 4-nitrophthalonitrile. Binuclear metallophthalocyanines 24 were obtained by the reaction between 4, 4'-(1, 4-phenylenebis(oxy)diphthalonitrile and 4-(benzo [d] 1,3 dioxol-5-ylmethoxy)phthalonitrile in the presence of metal salts. These new compounds were characterized by using elemental analysis, FTIR, 1H-NMR and UV/Vis spectroscopic data. Thermal properties of phthalocyanines 2-4 were investigated by TG and DTA. In addition, antioxidant properties of compounds II, 3 and 4 were investigated. Their radical-scavenging capacity and chelating effects was fully studied. The maximum 1, 1-diphenyl-2-picrylhydrazyl radicals (DPPH) were obtained from compound 3. Chelating effects on ferrous ions were 91.6?% at concentration of 100 mg?L1 with compound II.
Dna Cleavage Properties and Synthesis of Metallophthalocyanines With 5-Methyl Triazolo [1, 5-A] Pyrimidin-7 Substituents
(Taylor & Francis inc, 2017) Agirtas, M. Salih; Ondes, M. Yusuf; Ozdemir, Sadin; Okumus, Veysi
The aim of the present study is to perform synthesis of novel metallophthalocyanines (pcs) with high solubility. The synthesis and characterization of 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-yloxy-substituted zinc, magnesium, and cobalt pcs are reported. These compounds have been characterized using electronic absorption, nuclear magnetic resonance spectroscopy, infrared, elemental analysis and mass spectra. The aggregation investigations carried out in different concentrations indicate that 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-yloxy-substituted pc complexes do not have any aggregation behavior for the concentration range of 1 x 10(-5) -1 x 10(-6) M in THF. DPPH radical scavenging activity, metal chelating activity, and reducing power of the compounds were evaluated. The DNA gel electrophoresis studies revealed that new phthalonitrile and its metallophthalocyanine compounds cleavaged plasmid DNA (pBR322). Additionally, the ground-state geometries of the complexes were optimized using density functional theory methods at B3LYP/6-31G (d, p) level in order to obtain information about the 3D geometries and electronic structure.
Metallo Phthalocyanines Bearing (2-((2 (p-Tolyl)amino)ethoxy) and (2-((2 (p-Tolyl)amino)ethoxy)phthalonitrile Substituents: Synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity
(Elsevier Science Sa, 2014) Celebi, Metin; Agirtas, M. Salih; Okumus, Veysi; Ozdemir, Sadin
The novel phthalonitrile derivatives bearing (2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy) and (2-((2-phenoxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile substituents at peripheral position were prepared by a nucleophilic displacement reaction. Cyclotetramerization of these phthalonitrile derivatives in the presence of corresponding metal salts gave the new metallophthalocyanines. The novel compounds were characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-6) M in tetrahydrofuran. In vitro three antioxidant test methods, namely diphenylpicrylhydrazyl radical scavenging activity, metal chelating activity and reducing power were used to determine the antioxidant activity of compounds. Compounds were analyzed for their antibacterial activity against some bacteria by using the disk-diffusion method. (C) 2014 Elsevier B.V. All rights reserved.
Metallo Phthalocyanines Bearing 2-Isopropyl Substituents: Synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity, and Electronic Properties
(Wiley-v C H verlag Gmbh, 2014) Agirtas, M. Salih; Dede, Emrah; Gumus, Selcuk; Dundar, Abdurrahman; Okumus, Veysi
A novel phthalonitrile derivative bearing 2-isopropyl-6-methylpyrimidin-4-yloxy substituents at peripheral positions was synthesized by a nucleophilic substitution reaction. Metallophthalocyanines were obtained from the reaction of the novel phthalonitrile with metal Zn, Cu, Co, and Ni salts. The characterization of the compounds was performed using elemental analysis as well as UV/Vis, FT-IR, and H-1-NMR spectroscopy. The aggregation behaviors of phthalocyanine complexes were also investigated. These metallophthalocyanines do not show any aggregation behavior between 10 (4)-10 (6) M concentration range in THF. The antioxidant activities of the synthesized compounds were evaluated using three different tests: 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, metal chelating activity, and reducing power assays. All the compounds exhibited various antioxidant activities. In addition, antimicrobial activity of the compounds was tested over four gram positive and two gram negative bacteria. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D arrangements and electronic structure.
New Water Soluble Phenoxy Phenyl Diazenyl Benzoic Acid Substituted Phthalocyanine Derivatives: Synthesis, Antioxidant Activities, Atypical Aggregation Behavior and Electronic Properties
(Elsevier Sci Ltd, 2013) Agirtas, M. Salih; Celebi, Metin; Gumus, Selcuk; Ozdemir, Sadin; Okumus, Veysi
Novel substituted phthalonitrile derivatives were obtained by the reaction of 2-(4-hydroxyphenylazo) benzoic acid and 4,5-dichloro-1,2-dicyanobenzene, or 4-nitrophthalonitrile. Peripherally phenoxy phenyl diazenyl benzoic acid substituted zinc (II) phthalocyanine complexes, and their sodium salts were synthesized and characterized for the first time. The newly synthesized phthalocyanine complexes show excellent solubility in water. The aggregation investigations carried out in different concentrations indicate that phenoxy phenyl diazenyl benzoic acid-substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 7.00 x 10(-5)-4.38 x 10(-6) M in DMF. The antioxidant activities of DMF solution of compounds were analyzed through radical scavenging, and chelating ability to Fe2+ cation. Additionally, new compounds did not show any antibacterial activity against some selected bacteria cultures. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure. (C) 2013 Elsevier Ltd. All rights reserved.
Novel Cobalt(Ii), Zinc(Ii) Phthalocyanines Bearing Discrete Substituents: Synthesis, Characterization, Aggregation Behavior, Electrochemical Properties, and Antioxidant Activity
(Taylor & Francis inc, 2014) Agirtas, M. Salih; Cabir, Beyza; Dundar, Abdurrahman; Okumus, Veysi; Ceyhan, Gokhan
A new phthalonitrile derivative bearing 3,4,5-trimethoxy- benzyloxy and chloro-substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of phthalonitrile derivative in dimethylsulfoxide (DMSO) gave the metallophthalocyanines. Novel Co(II), Zn(II) phthalocyanines (Pcs) were obtained from the reaction 4-[(3,4,5-trimethoxybenzyloxy]-5-chlorophthalonitrile and metal salts. The novel compounds have been characterized by using elemental analysis, UV-Vis, FTIR, H-1-NMR spectral data. The aggregation behaviors of Co(II), Zn(II) Pcs were also investigated. These metallophthalocyanines do not show any aggregation behavior between 1.2 x 10(-5) and 4.0 x 10(-6) M concentration range in DMF. The antioxidant activities of Pcs were investigated antioxidant assays such as free radical scavenging ability of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and ferrous ion chelating ability. Furthermore, the redox properties of the Pcs complexes were investigated by using cyclic voltammetry.
Synthesis and Biological Evaluation of Quinoline-Triazole and Quinolone-Triazole Conjugates
(Tubitak Scientific & Technological Research Council Turkey, 2018) Gumus, Aysegul; Okumus, Veysi
One-pot synthesis of novel quinoline- and quinolone-substituted 1,2,3-triazoles has been performed from the key intermediates, quinoline- and quinolone-substituted propargyl derivatives 1-3 (48%-88% yields). The antioxidant properties of the newly synthesized compounds, 1a-1c, 2a-2c, and 3a-3c, were evaluated by monitoring DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging abilities, metal chelating effects, and reducing power. The scavenging effects of compounds on the free radical decreased in the order of 3b > 3a > 1b and were found to be 36.3%, 34.9%, and 27.6% at the concentration of 500 mu g/mL, respectively. All of the compounds showed low chelating capacity. Furthermore, the antibacterial activity was studied against gram-positive and gram-negative bacteria and the DNA binding ability of the compounds was evaluated with calf thymus DNA using agarose gel electrophoresis.
Synthesis of 2-Substituted 8-Propargyloxyquinoline Derivatives and Determination of Their Antioxidant, Antibacterial, and Dna Binding Activities
(Tubitak Scientific & Technological Research Council Turkey, 2018) Gumus, Aysegul; Okumus, Veysi; Gumus, Selcuk
2-Substituted 8-propargyloxyquinoline derivatives have been synthesized from 2-substituted-8-hydroxyquinolines by O-propargylation method (30%-98% yields). The newly synthesized compounds were tested for in vitro antioxidant activities such as DPPH radical scavenging, ferrous chelating, and reducing power activities. The maximum radical scavenging (46.5%) and reducing power activities were obtained from 1 and maximum ferrous chelating effect was obtained from 6 (72.1%) at the concentration of 500 mu g/mL. To indicate DNA binding activity of the complexes calf thymus DNA was used. The compounds were also evaluated for their antimicrobial activity against three gram-positive and three gram-negative bacteria. Compounds 3 and 5 exhibited antibacterial activity against all tested gram-positive bacteria.
Synthesis of Some Novel Phthalocyanines With Methyl 2-(oxy) Substituents, Evaluation of Their Antioxidant- Antibacterial Activities and Electronic Properties
(Wiley-v C H verlag Gmbh, 2015) Agirtas, M. Salih; Karatas, Ceyhun; Gumus, Selcuk; Okumus, Veysi
The synthesis, characterization, spectral, antioxidant, and antibacterial properties of methyl 2-(oxy)-2,2-diphenylacetate substituted metallophthalocyanines (4-7) are reported. A novel phthalonitrile, methyl 2-(2,3-dicyanophenoxy)-2,2-diphenylacetate (3) was prepared and characterized. The new compounds were characterized by using electronic absorption spectroscopy, nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. All compounds were tested for their antioxidant activity by using 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability, metal chelating, and reducing power. Furthermore, these compounds were screened for their in vitro growth inhibiting activity by disc diffusion method against four gram positive and two gram negative bacteria. The electronic data of the new compounds were obtained by computational calculations at B3LYP/6-31G(d,p) level of theory.
Synthesis, Aggregation, Antioxidant and Dna-Binding Properties of Metallophthalocyanines Bearing 5-Tert Groups
(Wiley-v C H verlag Gmbh, 2017) Agirtas, Mehmet Salih; Cabir, Beyza; Ozdemir, Sadin; Okumus, Veysi; Arslantas, Ali
In this study, the synthesis and characterization of new substituted metallophthalocyanines are described. A new phthalonitrile, 4-(5-tert-butyl-2-hydroxyphenoxy)-5-chlorophthalonitrile (3) was prepared. New compounds were characterized by UV-Vis, IR, H-1 NMR, and elemental analysis. The aggregation behavior of the cobalt (II), magnesium (II) and copper (II) phthalocyanines were studied in tetrahydrofuran and in known concentration ranges. The antioxidant activities of compounds were evaluated. Their radical-scavenging capacity, metal chelating activity and reducing power was fully studied. The compound 3 showed 100% chelating activity as EDTA at concentration 50 mg/L. The DNA interaction of copper (II) phthalocyanine compound (6) was studied using UV/Vis titration, gel electrophoresis, cyclic voltammetry. The results indicated that compound 6 interacts with CT-DNA via intercalation binding mode.
Synthesis, Biological Evaluation of Antioxidant-Antibacterial Activities and Computational Studies of Novel Anthracene- and Pyrene-Based Schiff Base Derivatives
(Tubitak Scientific & Technological Research Council Turkey, 2020) Gumus, Aysegul; Okumus, Veysi; Gumus, Selcuk
Schiff base derivatives with anthracene- and pyrene-based units, Al-A6 and P1-P6 were synthesized (89%-99% yields). Schiff base derivatives were designed to possess an heterocyclic moiety on one side to enhance the coordination ability towards metals. To investigate the biological assay of the newly synthesized compounds, their DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, metal chelating, reducing power, antibacterial and DNA binding activities were tested. A6 (63.1%) showed the maximum free radical scavenging activity among all. However, compound P3 at concentration of 200 mu g/mL possessed the highest metal chelating (45.8%) activity and power of reduction. In addition, P3 and A6 showed antibacterial activity against all bacteria tested and both compounds were very well bound to CT-DNA. Density functional theory method with B3LYP/6-311++ G(d,p) basis set was performed to get information about the structural and electronic properties of the present compounds. In addition, the metal coordination properties of the dimers of the parent Schiff bases were investigated through interactions with Zn2+.