14-Sep-2021 News The Shocking Revelation of 15804-19-0

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Cyclization of 2-amino-6-bromo-4-oxochromene-3-carboxamide (5) with diethyl oxalate-sodium ethoxide gave the benzopyrano<2,3-d>pyrimidine-4,6-dione (6).Ethyl 3-amino-2-carbamoyl-4-oxochromene-6-carboxylate (10a) in a similar reaction gave derivatives of a novel ring system benzopyrano<3,2-d>pyrimidine (8) but when 3-amino-4-oxochromene-2-carboxamide (10b) was subjected to the same reaction, the novel ring system benzopyrano<3,2-e>-1,4-diazepine (14a) was obtained in high yield.This structure, which contains the hitherto unknown 1,4-diazepine-2,3,5-trione ring, is supported by spectroscopic and chemical evidence.The presence of a 3-amino and a 2-carbonyl group in a chromone has an unexpected shielding effect on the chemical shift of C-8.The course of the cyclization was studied.Attempts to cyclize 3-aminomethyl-4-oxochromene-2-carboxamide (28; X= Y= H), a homologue of (10b), failed but a new ring system (31) was obtained when ethyl 3-bromo-4-oxochromene-2-carboxylate (29; R1= OEt) reacted with o-phenylenediamine.

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Reference:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N295 | ChemSpider

 

September 14,2021 News Awesome and Easy Science Experiments about 15804-19-0

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3-Aryl-1?H-spiro[2-pyrazoline-5,2?-quinoxalin] -3?(4?H)-ones, easily available by the reaction of 3-(2-aryl-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-ones with hydrazine hydrate (and phenylhydrazine), in boiling acetic acid undergo new acid-catalyzed rearrangement with the contraction of pyrazine ring of the quinoxaline system to form 2-(pyrazol-3-yl)benzimidazoles. Possible mechanisms of this rearrangement are considered.

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September 14,2021 News Archives for Chemistry Experiments of 15804-19-0

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Derivatives of the nonselective excitatory amino acid antagonist kynurenic acid (4-oxo-1,4-dihydroquinoline-2-carboxylic acid, 1) have been synthesized and evaluated for in vitro antagonist activity at the excitatory amino acid receptors sensitive to N-methyl-D-aspartic acid (NMDA), quisqualic acid (QUIS or AMPA), and kainic acid (KA). Introduction of substituents at the 5-, 7-, and 5,7-positions resulted in analogues having selective NMDA antagonist action, as a result of blockade of the glycine modulatory (or coagonist) site on the NMDA receptor. Regression analysis suggested a requirement for optimally sized, hydrophobic 5- and 7-substituents, with bulk tolerance being greater at the 5-position. Optimization led to the 5-iodo-7-chloro derivative (53), which is the most potent and selective glycine/NMDA antagonist to date (IC50 vs [3H]glycine binding, 32 nM; IC50’s for other excitatory amino acid receptor sites, >100 muM). Substitution of 1 at the 6-position resulted in compounds having selective non-NMDA antagonism and 8-substituted compounds were inactive at all receptors. The retention of glycine/NMDA antagonist activity in heterocyclic ring modified analogues, such as the oxanilide 69 and the 2-carboxybenzimidazole 70, suggests that the 4-oxo tautomer of 1 and its derivatives is required for activity. Structurally related quinoxaline-2,3-diones are also glycine/NMDA antagonists, but are not selective and are less potent than the 1 derivatives, and additionally show different structure-activity requirements for aromatic ring substitution. On the basis of these results, a model accounting for glycine receptor binding of the 1 derived antagonists is proposed, comprising (a) size-limited, hydrophobic binding of the benzene ring, (b) hydrogen-bond acceptance by the 4-oxo group, (c) hydrogen-bond donation by the 1-amino group, and (d) a Coulombic attraction of the 2-carboxylate. The model can also account for the binding of quinoxaline-2,3-diones, quinoxalic acids, and 2-carboxybenzimidazoles.

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Quinoxaline derivatives have attracted considerable attention due to their vast range of applications that includes electroluminescence and biomedicine. Concerning the latter, the literature has shown that compounds with a quinoxaline motif bind quite efficiently to phosphatidylinositol-4,5-bisphosphate 3-kinases (PI3Ks), which are enzymes found to be overexpressed in some types of neoplasms. In the present study, gold nanoparticles (AuNPs) were easily functionalized with 2,3-diethanolminoquinoxaline (DEQX) and 2-(2,3-dihydro-[1,4]oxazino[2,3-b]quinoxalin-4-yl)ethanol (OAQX). We made use of glycerol in alkaline media as reducing agent and the quinoxalines served as capping ligands to stabilize the AuNPs. This is the first report on the modification of a nanostructure with quinoxalines. Functionalization confers nanoparticles the required specificity to target only cancer cells, which opens possibilities for phototherapy since the modified AuNPs would concentrate in the tumor tissue as a consequence of PI3Kalpha overexpression. Molecular dynamics simulations have shown that DEQX and OAQX are potential inhibitors of PI3Kalpha since they bind to the active site of the enzyme in a way similar to other known inhibitors.

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Sep 2021 News Discover the magic of the 15804-19-0

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The present invention provides a compound of formula I shown in structure, synthesis method, and its pharmaceutically acceptable salt or their mixture in the preparation of the prevention and/or treating diabetes complications in the use of the medicament, such compounds as aldose reductase inhibitor and antioxidant, by inhibiting aldose reductase activity, while at the same time effectively eliminating free radical and inhibiting lipid peroxide generation, thereby preventing and/or treating diabetes complication. The invention also provides comprising such compounds with the prevention and/or treating diabetes complication effects of the pharmaceutical composition. (by machine translation)

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10/9/2021 News New explortion of 15804-19-0

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New Advances in Chemical Research, May 2021. In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. Electric Literature of 15804-19-0, In a article, mentioned the application of 15804-19-0, Name is Quinoxaline-2,3(1H,4H)-dione, molecular formula is C8H6N2O2

New transition metal complexes of quinoxaline-thiosemicarbazone ligands were prepared and characterised by spectroanalytical techniques. The ligands L1H2 and L2H2 were obtained by the reaction of quinoxaline-2.3(1,4H)-dione with methyl and phenyl thiosemicarbazide, respectively. All the complexes are found to be monomeric in nature and have tetrahedral geometry. The copper complexes have shown redox responses in the applied voltage range, whereas the ligands and other complexes are electrochemically innocent. The ligands, copper and zinc complexes are explored for antidiabetic activity in the diabetes-induced Wister rats. Evaluation of antidiabetic activity was done by blood-glucose test and oral glucose tolerance test; few compounds have exhibited significant antidiabetic activity and posses low toxicity with a high safety profile. Springer Science+Business Media, LLC 2011.

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September 10,2021 News Final Thoughts on Chemistry for 15804-19-0

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Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia, and surgery, as well as treating neurodegenerative diseases including Alzheimer”s disease, amyotrophic lateral sclerosis, Huntington”s disease, and Down”s syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, and inducing anesthesia are disclosed by administering to an animal in need of such treatment an alkyl or azido-substituted 1,4-dihydroquinoxaline-2,3-dione or pharmaceutically acceptable salts thereof, which have high binding to the glycine receptor.

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08/9/2021 News Chemical Properties and Facts of 15804-19-0

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AMPA Receptor antagonists have received considerable attention in recent years. Within the class of excitatory amino acid receptor antagonists AMPA receptor antagonists have shown excellent neuroprotection in several models of cerebral ischemia and neuronal injury. However, poor physical properties have been a major limiting factor in developing these as viable drug candidates. The quinoxaline-2,3-dione template has been the backbone of various competitive AMPA receptor antagonists such as NBQX, PNQX, YM-90K and more recently ZK200775. The SAR learned from these have been valuable for developing the AMPA pharmacophore model (Fig. 2) and has been discussed in detail in this review. There have been efforts in this area to design very selective AMPA receptor antagonists by minimizing the interaction at the NMDA associated GlyN receptors. Compounds designed by BASF and Yamanouchi have been successful in these efforts and their compounds show excellent affinity for the AMPA receptors. Efforts by Warner-Lambert and Novartis also highlight significant success in developing balanced AMPA and GlyN receptor antagonists. Non-competitive AMPA receptor antagonists are also being pursued for various neurological disorders including neuroprotection and are divided in two major classes, viz. positive and negative allosteric modulators. The physical properties of negative allosteric modulators such as GYK1 52466, which belong to the 2,3-benzodiazepinyl structural class have been significantly better. However, the in vitro activity of these compounds has been in the micromolar range and the overall class has the disadvantage of not having a high throughput assay. Other classes of compounds such as phthalazines and quinazolines are being developed and have raised hopes for the second generation of compounds in this area.

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The biological activity of Mannich bases, a structurally heterogeneous class of chemical compounds that are generated from various substrates through the introduction of an aminomethyl function by means of the Mannich reaction, is surveyed, with emphasis on the relationship between structure and biological activity. The review covers extensively the literature reports that have disclosed Mannich bases as anticancer and cytotoxic agents, or compounds with potential antibacterial and antifungal activity in the last decade. The most relevant studies on the activity of Mannich bases as antimycobacterial agents, antimalarials, or antiviral candidates have been included as well. The review contains also a thorough coverage of anticonvulsant, anti-inflammatory, analgesic and antioxidant activities of Mannich bases. In addition, several minor biological activities of Mannich bases, such as their ability to regulate blood pressure or inhibit platelet aggregation, their antiparasitic and anti-ulcer effects, as well as their use as agents for the treatment of mental disorders have been presented. The review gives in the end a brief overview of the potential of Mannich bases as inhibitors of various enzymes or ligands for several receptors.

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The ligand, N2,N3-bis(3-nitrophenyl)quinoxaline-2.3-diamine was prepared by the condensation of quinoxaline-2.3(1,4H)-dione with 3-nitroaniline. It was treated with Co(II), Ni(II), Cu(II) and Zn(II) acetates to form the metal complexes. These were characterized by elemental analysis, molar conductance, magnetic moment, UV?Vis., IR, 1H NMR, ESR and mass spectral data. Octahedral geometry has been assigned to Co(II), Ni(II) and Zn(II) complexes, whereas Cu(II) complex has distorted octahedral geometry. From the powder XRD data, crystallite size and unit cell parameters were calculated. The surface morphology of the synthesized compounds were determined using SEM analysis. The antimicrobial activity of the compounds against some bacterial species viz. Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeuruginosa and Staphylococcus aureus; also the fungal species, Aspergillus niger, and Candida albicans were done by disc diffusion method. DNA binding, cleavage and super oxide anion scavenging activities were also evaluated. The DNA binding activity of the compounds were identified using electronic absorption titrations and DNA cleavage was determined using gel electrophoresis. The anticancer activities of the compounds against HeLa cell line were determined using MTT assay. The highly potent compound among the five against HeLa cell line is subjected to molecular docking study against human papilloma virus receptor molecule and ATP binding site of telomerase.

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