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Study of molybdenum(4+) quinoxalyldithiolenes as models for the noninnocent pyranopterin in the molybdenum cofactor

A model system for the molybdenum cofactor has been developed that illustrates the noninnocent behavior of an N-heterocycle appended to a dithiolene chelate on molybdenum. The pyranopterin of the molybdenum cofactor is modeled by a quinoxalyldithiolene ligand (S2BMOQO) formed from the reaction of molybdenum tetrasulfide and quinoxalylalkyne. The resulting complexes TEA[TpMoX(S2BMOQO)] [1, X = S; 3, X = O; TEA = tetraethylammonium; Tp* = hydrotris(3,5-dimethylpyrazolyl)borate] undergo a dehydration-driven intramolecular cyclization within quinoxalyldithiolene, forming TpMoX(pyrrolo-S2BMOQO) (2, X = S; 4, X = O). 4 can be oxidized by one electron to produce the molybdenum(5+) complex 5. In a preliminary report of this work, evidence from X-ray crystallography, electronic absorption and resonance Raman spectroscopies, and density functional theory (DFT) bonding calculations revealed that 4 possesses an unusual asymmetric dithiolene chelate with significant thione-thiolate character. The results described here provide a detailed description of the reaction conditions that lead to the formation of 4. Data from cyclic voltammetry, additional DFT calculations, and several spectroscopic methods (IR, electronic absorption, resonance Raman, and electron paramagnetic resonance) have been used to characterize the properties of members in this suite of five Mo(S 2BMOQO) complexes and further substantiate the highly electron-withdrawing character of the pyrrolo-S2BMOQO ligand in 2, 4, and 5. This study of the unique noninnocent ligand S2BMOQO provides examples of the roles that the N-heterocycle pterin can play as an essential part of the molybdenum cofactor. The versatile nature of a dithiolene appended by heterocycles may aid in modulating the redox processes of the molybdenum center during the course of enzyme catalysis.

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Quinoxaline | C8H6N629 | ChemSpider

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 2213-63-0, name is 2,3-Dichloroquinoxaline, introducing its new discovery. Formula: C8H4Cl2N2

Cathodic stripping voltammetry of 2,3-dichloroquinoxaline and 1,4- dichlorophthalazine reactive dyes and their hydrolysis products: Reactive Red 41 and Reactive Red 96

Preliminary studies of the feasibility of monitoring by cathodic stripping voltammetry the hydrolysis of two further types of reactive dyes have been made. The azo reduction peak in differential pulse cathodic stripping voltammograms of the 2,3-dichloroquinoxaline reactive dye, Reactive Red 41, and in those of its hydrolysis product are sufficiently separated for the hydrolysis of Reactive Red 41 to be followed using the heights of these peaks. In the case of the 1,4-dichlorophthalazine reactive dye, Reactive Red 96, the azo peaks of the reactive and hydrolysed dyes are too close to be used to monitor the hydrolysis reaction, but peaks associated with reduction of the 1,4-dichlorophthalazine group are present which could be used to monitor the hydrolysis of Reactive Red 96.

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Final Thoughts on Chemistry for 2,3-Dichloroquinoxaline

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KYNURENINE PRODUCTION INHIBITOR

Provided is a kynurenine production inhibitor comprising a nitrogen-containing heterocyclic compound represented by formula (I): (wherein R50 and R51 may be the same or different and each represent a hydrogen atom or the like, G1 and G2 may be the same or different and each represent a nitrogen atom or the like, X represents formula (III): (wherein m1 and m2 may be the same or different and each represent an integer of 0 or 1, Y represents an oxygen atom or the like, and R6 and R7 may be the same or different and each represent a hydrogen atom or the like), R1 represents optionally substituted lower alkyl or the like, R2 represents a hydrogen atom or the like, and R3 represents optionally substituted lower alkyl or the like), and the like.

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N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides. A New Class of Potent and Selective Ligands at the Peripheral Renzodiazepine Receptor

We report the synthesis and the affinity data at both the peripheral (PBR) and the central benzodiazepine receptors of a series of N,N-dialkyl-2-phenylindol-3-ylglyoxylamide derivatives III, designed as conformationally constrained analogues of 2-phenylindole-3-acetamides II such as FGIN-1-27. Most of the new compounds showed a high specificity and affinity for PBR, with Ki in the nanomolar to subnanomolar range. The most potent ligands (4-7, 9, 13-27) stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classical ligands. The SARs of this new class of compounds are discussed.

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More research is needed about 2213-63-0

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Synthesis of Cyano-Substituted Heterocycles by Means of Tetraethylammonium Cyanide

Chloropyrimidines 2, 3 and Chlorquinazolines 9, 10, after conversion into trimethylammonio derivatives 4, 5, 11, 12, react with tetraethylammonium cyanide 1a under very mild conditions to give pyrimidine carbonitriles 6, 7 and quinazoline carbonitriles 13, 14.Direct synthesis of quinoxaline carbonitriles 19 is possible by reaction of chloroquinoxalines 15, 18 with 1a.

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Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2?-Bisquinoline Derivatives

An asymmetric hydrogenation of 2,2?-bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo- and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N-heterocyclic carbenes (NHCs), which are important but difficult to access.

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Efficient phosphine ligands for the one-pot palladium-catalyzed borylation/Suzuki-Miyaura cross-coupling reaction

We report the synthesis of 2-(anthracen-9-yl)-1H-inden-3-yl dicyclohexylphosphine and its use in palladium-catalyzed borylation/Suzuki-Miyaura cross-coupling reaction to prepare a variety of symmetrical and unsymmetrical biaryl compounds in excellent yield. This journal is

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Extracurricular laboratory:new discovery of 6-Nitroquinoxaline

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Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts

An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to alpha-hydroxycarbonyl compound. Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product.

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Synthesis of Condensed Quinoxalines. VI. Synthesis of 1H-Pyrazolo<3,4-b>quinoxaline N-Oxides and Related Compounds

Oxidation of 1H-pyrazolo<3,4-b>quinoxalines (1a: R=H, 1b: R=CH3) with m-chloroperbenzoic acid (MCPBA) gave the 4-oxides (2a, b).The structures of 2a, b were confirmed by synthesis, by condensing 2-chloroquinoxaline-3-carbaldehyde 4-oxide (6) with appropriate hydrazines.Further oxidation of 2a with MCPBA gave the 4,9-dioxide (8).Treatment of 1,2-dihydro-2-oxoquinoxaline-3-carboxamide (10) and 1,2-dihydro-2-oxoquinoxaline-3-carbonitrile 4-oxide (13) with a mixture of POCl3 and PCl5 or POCl3-dimethylformamide afforded 2-chloroquinoaline-3-carbonitrile (11) and its 4-oxide (14), respectively.When 11 and 14 were reacted with hydrazines, the correponding 3-amino-1H-pyrazolo<3,4-b>-quinoxalines (12a, b) and their 4-oxides (15a, b) were obtained in high yields.The reaction of ethyl 2-chloroquinoxaline-3-carboxylate (16) with hydrazine hydrate afforded a mixture of uncyclized products, N,N’-bis(2-ethoxycarbonyl-3-quinoxalinyl)hydrazine (17), ethyl 2-hydrazinoquinoxaline-3-carboxylate (18) and 2-hydrazinoquinoxaline-3-carbohydrazide (19).Keywords 1H-pyrazolo<3,4-b>quinoxaline 4-oxide; 1H-pyrazolo<3,4-b>quinoxaline 4,9-dioxide; 3-amino-1H-pyrazolo<3,4-b>quinoxaline 4-oxide; 2-chloroquinoxaline-3-carbaldehyde 4-oxide; hydrazine; N,N’-bis(2-ethoxycarbonyl-3-quinoxalinyl)hydrazine; ethyl 2-hydrazinoquinoxaline-3-carboxylate; 2-hydrazinoquinoxaline-3-carbohydrazide

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Reference of 18671-97-1, Because a catalyst decreases the height of the energy barrier, its presence increases the reaction rates of both the forward and the reverse reactions by the same amount.18671-97-1, Name is 2,6-Dichloroquinoxaline, molecular formula is C8H4Cl2N2. In a article£¬once mentioned of 18671-97-1

Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo

Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H4R) from which 2-(4-methyl-piperazin-l-yl)- quinoxaline (3) was identified as a new lead structure for H4R ligands. Exploration of the structure-activity relationship (SAR) of this scaffold led to the identification of 6,7-dichloro 3-(4-methylpiperazin-l-yl) quinoxalin-2(1H)-one (VUF 10214, 57) and 2-benzyl-3-(4-methyl-piperazin-l-yl) quinoxaline (VUF 10148, 20) as potent H4R ligands with nanomolar affinities. In vivo studies in the rat reveal that compound 57 has significant anti-inflammatory properties in the carrageenan-induced paw-edema model.

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