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Öğe DNA cleavage properties and synthesis of metallophthalocyanines with 5-methyl-[1,2,4] triazolo [1, 5-a] pyrimidin-7-oxy substituents(Taylor & Francis Inc, 2017) Agirtas, M. Salih; Ondes, M. Yusuf; Ozdemir, Sadin; Okumus, VeysiThe 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.Öğe Metallo and metal free phthalocyanines bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents: Synthesis, characterization, aggregation behavior, electronic, antioxidant and antibacterial properties(Elsevier Science Sa, 2014) Agirtas, M. Salih; Guven, M. Emin; Gumus, Selcuk; Ozdemir, Sadin; Dundar, AbdurrahmanAs starting material the phthalonitrile derivative bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile derivative in the presence of corresponding metal salts gave the new metallophthalocyanines. Metal free phthalocyanine was obtained from the reaction of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile units. The novel compounds have been characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-5) M in tetrahydrofuran. The antioxidant activities of novel compounds were analyzed through radical scavenging ability of 1,1-dipheny1-2-picrylhydrazyl, chelating ability to ferrous ions and reducing power. In addition to these, the antibacterial activities of compounds were investigated. Moreover, the ground-state geometries of the complexes were optimized using B3LYP/6-31G(d,p) level of density functional theory in order to predict the three-dimensional geometries and electronic structure. (C) 2014 Elsevier B.V. All rights reserved.Öğe Metallo phthalocyanines bearing (2-((2-hydroxyethyl) (p-tolyl)amino)ethoxy) and (2-((2-phenoxyethyl) (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, SadinThe 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.Öğe Metallo Phthalocyanines bearing 2-Isopropyl-6-methylpyrimidin-4-yloxy 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, VeysiA 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.Öğe 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, VeysiNovel 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.Öğe 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, GokhanA 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.Öğe Novel metal (II) phthalocyanines with 3,4,5-trimethoxybenzyloxy-substituents: Synthesis, characterization, aggregation behaviour and antioxidant activity(Elsevier Sci Ltd, 2013) Agirtas, M. Salih; Cabir, Beyza; Ozdemir, SadinA new substituted phthalonitrile derivative was prepared by a nucleophilic displacement reaction of 3,4,5-trimethoxybenzyl alcohol with 4-nitrophthalonitrile. Novel metallophthalocyanines IM: Zn (II), Co (II), Ni (II)1 with four peripheral 3,4,5-trimethoxybenzyloxy groups were synthesized by cyclotetramerization of phthalonitrile derivative. These compounds were purified by crystallization and column chromatography. They were characterized by elemental analysis, FTIR, H-1 NMR, C-13 NMR and UV-VIS spectral data. The aggregation investigations carried out in different concentrations indicate that 3,4,5-trimethoxybenzyloxy-substituted phthalocyanine compounds do not have any aggregation behaviour in concentration range of 10(-2)-10(-8) M. The antioxidant activities of phthalocyanines were investigated by in vitro antioxidant assays such as free radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferrous ion chelating ability. The highest DPPH activity and ferrous ion chelating activity were obtained from Tetrakis [(3,4,5-trimethoxybenzyloxy) phthalocyaninato] cobalt and 4-(3,4,5-trimethoxybenzyloxy) phthalonitrile, respectively. 4-(3,4,5-trimethoxybenzyloxy) phthalonitrile was shown to have a fairly ferrous ion chelating activity. (C) 2012 Elsevier Ltd. All rights reserved.Öğe Synthesis of some metallophthalocyanines with dimethyl 5-(phenoxy)-isophthalate substituents and evaluation of their antioxidant-antibacterial activities(Pergamon-Elsevier Science Ltd, 2015) Agirtas, M. Salih; Karatas, Ceyhun; Ozdemir, SadinThe synthesis, characterization, spectral, antioxidant and antibacterial properties of dimethyl 5-(phenoxy)-isophthalate substituted Zinc, Cobalt, Copper, and Nickel phthalocyanines are reported. The novel compounds have been characterized by using electronic absorption, nuclear magnetic resonance spectroscopy, infrared, elemental analysis and mass spectrometry. The antioxidant and antibacterial activities of newly synthesized phthalocyanines and its starting material are tested. The DPPH free radical scavenging ability of phthalocyanine Co(II) and Zn(II) complexes on DPPH are 44.8% and 40.1% at 100 mg/L concentration, respectively. The phthalocyanine Co(II) and Cu(II) complexes show very strong ferrous ion chelating activity of 91.2% and 89.3% at concentration of 100 mg/L, respectively. Compound 3 displays strong reducing power like alpha-tocopherol. Antibacterial activities of phthalocyanine Co(II) and Amikacin (30 mu g/disk) against Micrococcus luteus (ATCC 9341) are 16 mm in diameter. (C) 2014 Elsevier B.V. All rights reserved.Öğe Synthesis of Some Novel Phthalocyanines with Methyl 2-(oxy)-2,2-diphenylacetate 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, VeysiThe 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.Öğe SYNTHESIS, CHARACTERIZATION, AGGREGATION BEHAVIOR, ANTIOXIDANT ACTIVITY, AND ANTIBACTERIAL ACTIVITY OF METALLOPHTHALOCYANINES CARRYING FOUR PHTHALONITRILES GROUP(Editura Acad Romane, 2016) Guven, M. Emin; Agirtas, M. Salih; Ozdemir, Sadin; Dundar, AbdurrahmanA novel phthalonitrile derivative and zinc (II), cobalt (II), and cupper (II) phthalocyanines complexes were synthesis and characterized. The novel compounds have been characterized by using various spectroscopic data FTIR, UV/vis, NMR, elemental analysis etc. The aggregation investigations carried out in different concentrations indicate that 4- (4-(1-(4-phenoxypheny1)-1-phenylethyl)phenoxy)phthalonitrile substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-5) M in tetrahydrofuran. The antioxidant properties of the phthalonitrile and its phthalocyanine compounds were evaluated in three series of in vitro tests: DPPH free radical scavenging, ferrous ion chelating activity and reducing power. Antimicrobial activities of compounds were investigated.