- Synthesis and Antitumor Evaluation of Selected 5,6-Disubstituted 1(2)H-Indazole-4,7-diones
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A series of novel aziridinyl-substituted 1(2)H-indazole-4,7-diones and related 1(2)H-indazole-4,7-diones was synthesized and tested against Ehrlich ascites carcinoma growth in male CF1 mice.Ten of the test compounds, including two aziridinyl-su
- Conway, Gregory A.,Loeffler, Larry J.,Hall, Iris H.
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- (E)-4-(4-(3-(2-fluoro-5-(trifluoromethyl)phenyl)acryloyl)phenoxy)Substituted Co(II)and Cu(II)phthalocyanines and their catalytic activities on the oxidation of phenols
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Phenols from various man-made activities pose threats to public health and aquatic ecosystems. A number of technologies (e.g., adsorption, oxidation, and biological methods)have been proposed and tested to remove phenolic compounds from different sources. Among these technologies, oxidation process is considered one of the most efficient tools for abating phenolic compounds because of low cost, easy scalability, and ecofriendly production. In this work, we aim to synthesize and characterize potential catalysts (Co(II)and Cu(II)phthalocyanines 6 and 7)for phenolic compounds oxidation. Different parameters influenced the oxidation process were determined and phenolic compounds oxidize to the less harmful products with high conversion and yield in the presence of Co(II)and Cu(II)phthalocyanine catalysts.
- Saka, Ece Tugba,Kahriman, Nuran
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supporting information
p. 48 - 54
(2019/06/05)
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- Degradation of substituted phenols with different oxygen sources catalyzed by Co(II) and Cu(II) phthalocyanine complexes
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Research on substituted phenol degradations has received substantial attention. In this work, effective Co(II) and Cu(II) phthalocyanine complexes as catalysts were studied to degrade toxic phenols to harmless products. The effect of various process parameters, such as initial concentration of phenol, catalyst, oxygen sources, and temperature on the degradation reaction was investigated to achieve maximum degradation efficiency. The catalytic activities of Co(II) and Cu(II) phthalocyanines were evaluated for oxidation of phenolic compounds such as p-nitrophenol, o-chlorophenol, 2,3-dichlorophenol, and m-methoxyphenol. Co(II) phthalocyanine displayed good catalytic performance in degradation of 2,3-dichlorophenol to 2,3-dichlorobenzaldehyde and 2,3-dichloro-1,4-benzoquinone with the highest TON and TOF values within 3 h at 50 °C. The fate of catalyst during the degradation process was followed by UV–Vis spectroscopy.
- Saka, Ece Tugba,Dügdü, Esra,ünver, Yasemin
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p. 1119 - 1130
(2019/05/17)
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- New peripherally tetra-[trans-3,7-dimethyl-2,6-octadien-1-ol] substituted metallophthalocyanines: synthesis, characterization and catalytic activity studies on the oxidation of phenolic compounds
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In this paper, we elucidated the synthesis, characterization, and investigation of catalytic activity studies of new metallophthalocyanines 4 and 5 as the catalyst for phenolic compounds oxidation by trying different types of oxygen sources. The structural characterization of the products was made by a combination of elemental analysis, FT-IR, LC-MS/MS (for phthalonitrile derivative?3), MALDI-TOF mass spectral data (for metallophthalocyanines 4–7), UV–vis spectroscopy (for metallophthalocyanines 4–7), 1H NMR and 13C NMR spectroscopies (for compounds 3 and 6). The synthetic routes for the (trans-3,7-dimethyl-2,6-octadien-1-ol) substituted phthalonitrile derivative 3 and corresponding metallophthalocyanines 4–7 are outlined in Scheme 1. The MPc complexes 4–7 were synthesized via cyclotetramerization of compound 3 in the presence of the corresponding anhydrous metal salts (CoCl2 for 4, CuCl2 for 5, Zn(CH3COO)2 for 6 and MnCl2 for 7) in dry n-pentanol as solvent and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as strong base at reflux temperature under nitrogen gas. Phthalocyanines and their metal complexes, in general, display poor solubility in most of the organic solvents, however, the synthesized metallophthalocyanine complexes 4–7 were highly soluble in common organic solvents because of the introduction of the methyl groups on alkyl chains of peripheral arms. The catalytic activity of compounds 4 and 5 was evaluated for the oxidation of phenolic compounds such as 4-nitrophenol, o-chlorophenol, 2,3-dichlorophenol, and p-methoxyphenol. CoPc 4 displayed good catalytic performance with a full oxidation of 4-nitrophenol into the corresponding benzoquinone and hydroquinone with the highest TON and TOF values within 3?h.
- Kantekin, Halit,Saka, Ece Tu?ba,Ertem, Beytullah,M?s?r, Mira? Nedim,Yalazan, Halise,Sark?, Gülb?nar
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p. 164 - 182
(2018/02/06)
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- Preparation, characterization of new Co(II) and Cu(II) phthalocyanines and their catalytic performances in aerobic oxidation of substituted phenols
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Substituted phenol pollutants are produced as by products of many industrial processes. Aerobic oxidations for their degradation in the context of effluent treatment or environmental remediation often lack selectivity. In this work Co(II) and Cu(II) phthalocyanines-catalyzed approach is described that converts substituted phenols into less harmfull products. New cobalt(II) and copper(II) phthalocyanine complexes are used as catalyst for degradation of substituted phenols with different oxidants. The oxidation process exhibits remarkable selectivity and conversion owing to the fact that Co(II) and Cu(II) phthalocyanines work with high performance.
- Saka, Ece Tugba
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- Anthracene Substituted Co (II) and Cu (II) phthalocyanines; Preparations, Investigation of Catalytical and Electrochemical Behaviors
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An approach to investigation of catalytical behaviors of Co (II) and Cu (II) phthalocyanines is reported that is based on changing any parameter to effect these behaviors. Towards this end, new anthracene substituted Co (II) and Cu (II) phthalocyanines were prepared and characterized spectroscopic methods. New cobalt (II) and copper (II) phthalocyanines were used as catalyst for oxidation of different phenolic compounds (such as 2,3-dichlorophenol, 4-methoxyphenol, 4-nitrophenol, 2,3,6-trimethylphenol) with different oxidants. Then, electrochemical characterization of cobalt (II) and copper (II) phthallocyanines were determined by using cyclic voltammetry (CV) and square wave voltammetry (SWV) techniques. Although copper (II) phthalocyanine showed similar Pc based electron transfer processes, cobalt (II) phthalocyanine showed metal and ligand based reduction reactions as expected.
- Saka, Ece Tugba,Biyiklioglu, Zekeriya,Caglar, Yasemin
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- New Co(II) and Cu(II) Phthalocyanine Catalysts Reinforced by Long Alkyl Chains for the Degradation of Organic Pollutants
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Abstract: The need to develop sustainable, low-cost, earth abundant catalyst is becoming paramount for overcoming environmental problems. Toward this goal, new cobalt(II) and copper(II) phthalocyanine complexes used as catalyst for degradation of organic pollutants (such as 2,3-dichlorophenol, 4-methoxyphenol, 4-nitrophenol, 2,3,6-trimethylphenol) with different oxygen source. This catalytic system with these complexes showed high conversion rates for degradation of organic pollutants and could easily be recovered by recycling reactions. Graphical Abstract: [Figure not available: see fulltext.].
- Saka, Ece Tugba,?a?lar, Yasemin
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p. 1471 - 1477
(2017/05/17)
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- Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones
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Thirty four halogen and selenium-containing quinones, synthesized by rhodium-catalyzed C-H bond activation and palladium-catalyzed cross-coupling reactions, were evaluated against bloodstream trypomastigotes of T.?cruzi. We have identified fifteen compounds with IC50/24?h values of less than 2?μM. Electrochemical studies on A-ring functionalized naphthoquinones were also performed aiming to correlate redox properties with trypanocidal activity. For instance, (E)-5-styryl-1,4-naphthoquinone 59 and 5,8-diiodo-1,4-naphthoquinone 3, which are around fifty fold more active than the standard drug benznidazole, are potential derivatives for further investigation. These compounds represent powerful new agents useful in Chagas disease therapy.
- Jardim, Guilherme A.M.,Silva, Thaissa L.,Goulart, Marilia O.F.,de Simone, Carlos A.,Barbosa, Juliana M.C.,Salom?o, Kelly,de Castro, Solange L.,Bower, John F.,da Silva Júnior, Eufranio N.
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supporting information
p. 406 - 419
(2017/05/19)
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- Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C-H Iodination, Bromination, and Phenylselenation
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Under Rh-catalyzed conditions, typically electrophilic 1,4-benzoquinones exhibit nucleophilic reactivity, such that exposure to appropriate electrophiles generates products of C-H iodination, bromination, and phenylselenation. This provides a mild and general method for direct halofunctionalization, and the first method that can achieve direct C-H phenylselenation of this compound class. The scope and limitations of the new protocols are outlined, and representative derivatizations are highlighted.
- Jardim, Guilherme A. M.,Bower, John F.,Da Silva Júnior, Eufranio N.
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p. 4454 - 4457
(2016/09/28)
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- Quinone-based, redox-active resorcin[4]arene cavitands
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Catch it if you can! Redox-active resorcin[4]arene cavitands with quinone walls can be reversibly reduced to the hydroquinone form, influencing their host-guest complexation strength. Specifically, a top-covered triptycenequinone cavitand forms kineticall
- Pochorovski, Igor,Boudon, Corinne,Gisselbrecht, Jean-Paul,Ebert, Marc-Olivier,Schweizer, W. Bernd,Diederich, Francois
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supporting information; experimental part
p. 262 - 266
(2012/03/26)
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- BENZOFURAN-4,5-DIONES AS SELECTIVE PEPTIDE DEFORMYLASE INHIBITORS
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The instant invention provides novel benzofuran-4,5-diones and pharmaceutical compositions thereof useful for inhibiting PDF and for treating proliferative and infectious diseases. Compounds may be selective for eukaryotic (e.g., human) PDF or prokaryotic PDF
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Page/Page column 111; 113
(2010/11/18)
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- Convenient preparations of the three 2,3-dihalo-1,4-benzoquinones
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Efficient preparations of 2,3-dichloro-1,4-benzoquinone (1) and 2,3- dibromo-1,4-benzoquinone (2) from 1,4-benzoquinone are reported, as is the synthesis of the previously unknown 2,3-diiodo-1,4-benzoquinone (3) from 2.
- Yu, Duyi,Mattern, Daniell Lewis
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p. 821 - 825
(2007/10/03)
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- ELECTROCHEMICAL BEHAVIOUR OF SUBSTITUTED HYDROQUINONES
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The oxidation potentials of thirteen hydroquinones substituted by chlorine, pyrazol-1-yl and 3,5-dimethylpyrazol-1-yl groups were experimentally determined by cyclic voltammetry.The estimated half-wave potentials E1/2 have been discussed taking into account the inductive and conjugative substituent effects.Key words: Cyclic voltammetry, Hydroquinones, Redox, Pyrazoles
- Claramunt, R. M.,Escolastico, C.,Maria, M. D. Santa,Lopez, V.
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p. 368 - 371
(2007/10/02)
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- Synthesis of Perfragilin B, A Cytotoxic Isoquinoline Quinone Isolated from the Bryozoan Membranipora perfragilis
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The cytotoxic isoquinoline quinone perfragilin B (2), which was isolated from the bryozoan Membranipora perfragilis, has been synthesized.The key step involves a Diels-Alder reaction between a substituted 2-azabutadiene (4) and 2,3-bis(thiomethyl)-1,4-benzoquinone (6) to produce the isoquinoline skeleton.
- Park, Aeri,Schmitz, Francis J.
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p. 3983 - 3984
(2007/10/02)
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- The Kinetics and Mechanisms of Additions to Olefinic Substances. Part 16. Addition of Halogens to 1,4-Benzoquinone and to 1,4-Naphthoquinone, and Dehydrohalogenation of the Resulting Adducts
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The products of acid catalysed halogenation of 1,4-benzoquinone and 1,4-naphthoquinone in acetic acid have been investigated under conditions which could lead to the formation of dichloride, dibromide, and bromochloride.The variation in ratio of bromochloride to dibromide with relative availability of bromine and chlorine as electrophile and nucleophile suggests that the first entering halogen atom is attached nucleophilically as the result of '1,4'- (rather than then '1,2'-) addition, and that the second halogen atom is then attached electrophilically.Acetate ion does not compete effectively with chloride ion in the nucleophilic stage of the reaction; and chlorine acetate does not add, even with sulphuric acid as catalyst, to 1,4-benzoquinone.The mechanistic significance of these results is discussed.The kinetics and products of solvolytic eliminations from the dihalides derived from 1,4-benzoquinone have been studied in 95percent ethanol; the effects of structure on the rate make it probable that the reactions lie towards the E1cB end of the spectrum of elimination mechanisms.
- Atkinson, Romily C.,Mare, Peter B. D. de la,Larsen, David S.
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p. 271 - 280
(2007/10/02)
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