New explortion of Quinoxaline-2,3(1H,4H)-dione

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Ytterbium triflate catalyzed heterocyclization of 1,2-phenylenediamines and alkyl oxalates under solvent-free conditions via phillips reaction: A facile synthesis of quinoxaline-2,3-diones derivatives

Ytterbium triflate are found to catalyze efficiently the Phillips-type heterocyclization reactions of 1,2-phenylenediamine and alkyl oxalate under solvent-free and mild conditions to afford the corresponding quinoxaline-2,3-dione derivatives in high yields. The catalyst could be recovered almost quantitatively from the aqueous layer after the reaction was completed and it could be reused in subsequent reaction without decrease in activity.

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Structure-activity relationships of acetylcholinesterase noncovalent inhibitors based on a polyamine backbone. 4. Further investigation on the inner spacer

Novel multi-target-directed ligands were designed by replacing the inner dipiperidino function of 3 with less flexible or completely rigid moieties to obtain compounds endowed with multiple biological properties that might be relevant to Alzheimer’s disease. 15 was the most interesting, inhibiting AChE in the nanomolar range and inhibiting AChE-induced and self-promoted beta-amyloid aggregation in the micromolar range.

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Brief introduction of Quinoxaline-2,3(1H,4H)-dione

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Antagonist pharmacology of kainate- and alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-preferring receptors

Whole-cell recordings were used to study the antagonist pharmacology of two subtypes of non-N-methyl-D-aspartate glutamate receptors: the kainate-preferring subtype expressed by rat dorsal root ganglion (DRG) neurons and the alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA)-preferring subtype expressed by neurons from rat cerebral cortex. A series of quinoxaline derivatives were tested for the ability to distinguish between AMPA and kainate receptors, as determined by differential potency. Of the nine compounds studied, 2,3-dihydroxy-6-nitro-7-sulfamoylbenzo(f)quinoxaline (NBQX) snowed the highest selectivity for AMPA-preferring receptors, whereas 5-chloro-7-trifluoromethyl-2,3-quinoxalinedione (ACEA-1011) showed the highest selectivity for the kainate-preferring subtype. NBQX blocked non-N-methyl-D-aspartate currents in cortical cells with a Kb of 0.3 muM, but in DRG neurons the Kb for NBQX was 3-fold higher (0.9 muM). ACEA-1011 also blocked the currents in DRG cells with a Kb of ?1 muM, but in cortical neurons the Kb for this drug was 10-12 muM. Several additional compounds were tested for selective potency, including 5-nitro-6,7,8,9-tetrahydrobenzo[G]indole-2,3-dione-3-oxime, gamma-D-glutamylaminomethylsulphonic acid, and derivatives of kynurenic acid and 1-benzazepine. 5-Nitro-6,7,8,9-tetrahydrobenzo[G]indole-2,3-dione-3-oxime displayed the highest selectivity in this group, blocking kainate receptors with a Kb of 6 muM while inhibiting AMPA receptors with a Kb of >100 muM. The remaining antagonists showed <3-fold selectivity between AMPA and kainate receptor subtypes. Our results suggest that most competitive antagonists block native AMPA and kainate receptors with approximately similar potencies, which is in marked contrast to the substantial differences in potency that have been observed with receptor agonists. The proportionality constant is the rate constant for the particular unimolecular reaction. the reaction rate is directly proportional to the concentration of the reactant. I hope my blog about 15804-19-0 is helpful to your research. Application of 15804-19-0

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Non-symmetrical three and two-core ring mesogens based on quinoxaline and benzimidazole derivatives: Supramolecular layers through amphoteric donating/accepting H-bonds

Self-assembly-based molecular structures have proven to be highly relevant to the development of soft materials. This work reports the synthesis, thermal behavior and computational analysis of two novel heterocyclic compounds with a non-symmetrical shape bearing a single long alkyl (C12) chain. The compounds 2-(4-dodecyloxy-phenyl)-1H-benzoimidazole, 1, with three-ring core mesogen with a more linear shape, and 1-dodecyl-1,4-dihydro-quinoxaline-2,3-dione, 2, with a condensed two-ring core with a more compact discotic shape, were obtained in good yields and investigated by polarized optical microscopy (POM) and differential scanning calorimetry (DSC) analysis. Benzimidazole derivative 1 was found to present liquid crystalline property, with a mesophase range from 85 to 177 C, as verified by POM and DSC, with a smectogenic polymorphism assigned as a SmB and a more organized unidentified SmX phase. On the other hand, although quinoxaline 2 did not show liquid crystal behavior, POM analysis indicated an interesting spherulitic packing pattern, typical of a columnar arrangement of the molecules by possible H-bond interactions. Computational results indicated that combining intermolecular hydrogen bonds and hydrophobic interactions lead to a non-planar lamellar model for benzimidazole 1, consistent with the smectic packing found in the liquid crystalline phase and a twist-type packing for compound 2, which is consistent with a spherulitic model.

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Synthesis and antimicrobial activity of novel thiazolidinone and azetidinone derivatives

Reaction of 2,3-diketoquinoxaline in presence of phosphorus pentachloride and hydrazine hydrate gives 2-hydrazino-3-hydroxyquinoxalin (4) which on treatment with various aldehydes in appropriate solvent gives 2-p-anisyl-3-(3-hydroxy quinoxalin-2 yl-amino)-4-thiazolidinones (6) and 1-N-(3-hydroxy quinoxalin-2’yl-amino)-4-aryl-3-chloro-2-azetidinones (7). The structure of compounds 6a-6l and 7a-7l has been confirmed by IR and 1H NMR data. All these compounds were tested for their antimicrobial and antifungal activity against different microorganisms.

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Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones

Thiamine hydrochloride catalyzed synthesis of amides from ketones including 3-acetyl coumarin via Beckmann rearrangement has been reported. The reaction is believed to involve oxime formation, cleavage of C[sbnd]C bond followed by C[sbnd]N bond formation in one-pot. Thiamine hydrochloride is stable, cheap, easy to handle and environmentally friendly.

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Structure-activity relationships in a series of 3-sulfonylamino-2-(1H)-quinolones, as new AMPA/kainate and glycine antagonists

This paper describes the design and synthesis of a new class of molecules, the 3-sulfonylamino-2-(1H)-quinolones, which are potent and selective antagonists at both the AMPA/kainate site as well as at the NMDA-associated glycine site. The molecules were characterized by their binding affinities to rat cortical membranes and by electrophysiology on Xenopus oocytes injected with mRNA isolated from rat cerebral cortex. The most potent compound 61 has an IC50 of 0.09 muM for binding at the AMPA/kainate site, and 0.16 muM in oocyte electrophysiology.

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Crystal structure, infrared spectra and density functional theory study on 2,3-diketo-benzopiperazine dimer

2,3-Diketo-benzopiperazine, which exists as dimeric form in its crystal structure has been synthesized. The calculated results on the dimer at B3LYP/6-31G* level show that the average strength of the double hydrogen bonds is of medium-grade. Natural bond orbital analyses have been performed. The predicted harmonic vibration frequencies support the experimental values. The thermodynamic properties of the dimer at different temperatures have been calculated and the change of Gibbs free energy for the aggregation from the monomer to the dimer DeltaGr = -30.86 kJ/mol at 298.15 K, which implies the spontaneous process of the dimer formation.

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New explortion of 15804-19-0

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Formula: C8H6N2O2, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 15804-19-0, in my other articles.

One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, Formula: C8H6N2O2, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 15804-19-0, Name is Quinoxaline-2,3(1H,4H)-dione, molecular formula is C8H6N2O2

Studies on synthesis of 2-acetylbenzimidazole and related benzimidazole derivatives

Condensation of o-phenylenediamine (1) with propanoic acid under Phillips’ conditions gives 2-ethylbenzimidazole (2). Attempts to oxidise 2 to 2-acetylbenzimidazole (3) using H2O2, SeO2, KMnO4/acetone were unsuccessful. Condensation of 2 with benzaldehyde yields 2-(alpha-methylstyryl)benzimidazole (4) which on oxidation with KMnO4 gives benzimidazole-2-carboxylic acid (5) as the sole product. Reaction of 1 with pyruvic acid results in 3-methylbenzo-1H-dihydropyrazine-2-one (7) rather than 3 as the major product. Treatment of 1 with formic acid gives the known compound benzimidazole (9) which with acetic anhydride in the presence of NaOAc does not yield 3. Reaction of 1 with lactic acid under Phillips’ conditions gives 2-(alpha-hydroxyethyl)benzimidazole (10) which on oxidation with acid dichromate, however, yields 3. Studies on syntheses and spectral properties of related benzimidazoles are reported.

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Quinoxaline – Wikipedia,
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Design, synthesis and biological evaluation of quinoxaline compounds as anti-HIV agents targeting reverse transcriptase enzyme

Infection by human immunodeficiency virus still represents a continuous serious concern and a global threat to human health. Due to appearance of multi-resistant virus strains and the serious adverse side effects of the antiretroviral therapy administered, there is an urgent need for the development of new treatment agents, more active, less toxic and with increased tolerability to mutations. Quinoxaline derivatives are an emergent class of heterocyclic compounds with a wide spectrum of biological activities and therapeutic applications. These types of compounds have also shown high potency in the inhibition of HIV reverse transcriptase and HIV replication in cell culture. For these reasons we propose, in this work, the design, synthesis and biological evaluation of quinoxaline derivatives targeting HIV reverse transcriptase enzyme. For this, we first carried out a structure-based development of target-specific compound virtual chemical library of quinoxaline derivatives. The rational construction of the virtual chemical library was based on previously assigned pharmacophore features. This library was processed by a virtual screening protocol employing molecular docking and 3D-QSAR. Twenty-five quinoxaline compounds were selected for synthesis in the basis of their docking and 3D-QSAR scores and chemical synthetic simplicity. They were evaluated as inhibitors of the recombinant wild-type reverse transcriptase enzyme. Finally, the anti-HIV activity and cytotoxicity of the synthesized quinoxaline compounds with highest reverse transcriptase inhibitory capabilities was evaluated. This simple screening strategy led to the discovery of two selective and potent quinoxaline reverse transcriptase inhibitors with high selectivity index.

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