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Investigation of the antitumor activity of new epoxide derivatives. II: N-glycidylated oxo-nitrogen heterocyles

A number of N-glycidyl compounds derived from oxo-substituted nitrogen heterocycles such as diazines, triazines, diazoles, triazoles as well as condensed ring systems containing these units have been synthesized. All products were tested for their antitumor activity against leukaemia in the mouse. Almost all of the approx. 50 di- and triglycidyl compounds showed activity and 5 of them exhibited an increase of lifespan of 200% and more. The most active compound was 1,2,4-triglycidyl-urazol.

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Quinoxaline – Wikipedia,
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Synthesis of Pyrido<1',2':1,2>imidazo<4,5-b>quinoxalines

Synthesis of pyrido<1',2':1,2>imidazo<4,5-b>quinoxalines by the facile cyclizations of 2,3-dichloroquinoxalines with 2-aminopyridines and of 2-amino-3-chloroquinoxalines with various substituted pyridines is described.

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Electric Literature of 15804-19-0, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 15804-19-0, molcular formula is C8H6N2O2, introducing its new discovery.

Formation of 1-phenyl-4-oxo [1,2,4]triazolo[4,3-a]quinoxaline from 2- chloro-3-(2′-benzylidenehydrazino)quinoxaline during dehydrogenative cyclisation using cupric acetate

Attempted dehydrogenative cyclisation of 2-chloro-3-(2′- benzylidinchydrazino)quinoxaline 5 with a view to prepare 1-phenyl-4-chloro- [1,2,4]-triazolo [4, 3-a]quinoxaline 6 using cupric acetate gives 1-phenyl-4- oxo-[1,2,4]triazolo[4,3-a]quinoxaline 7. A rational explanation is offered for this reaction and the applicability of cupric acetate as dehydrogenative cyclisation agent (such as in the conversion of 10?11) has been demonstrated.

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Water superstructures within organic arrays; hydrogen-bonded water sheets, chains and clusters

A strategy for encouraging the formation of extended water arrays is presented, in which molecules that contain a 1,4-dihydroquinoxaline-2,3-dione core are used as supramolecular hosts for the accommodation of guest water molecules and arrays. These molecules were selected as they contain a hydrophilic oxalamide-based “terminus” that allows water molecules to hydrogen-bond to the host organic molecules as well as to each other. The host molecules also contain a hydrophobic “end” based upon an aromatic ring, which serves to encourage the formation of discrete water clusters in preference to three-dimensional networks, as the water molecules cannot form strong hydrogen bonds with this part of the molecule. A systematic study of several hydrated structures of four organic molecules based on 1,4-dihydroquinoxaline-2,3-dione (qd) is discussed. The organic molecules, qd, 6-methyl-1,4-dihydroquinoxaline-2,3-dione (mqd), 6,7-dimethyl-1,4- dihydroquinoxaline-2,3-dione (dmqd) and 1,4-dihydrobenzo[g]-quinoxaline-2,3- dione (Phqd), act as supramolecular crystal hosts for the clusters of water, with zero-, one- and two-dimensional arrays of water being observed. The hydrogen bonding in the structures, both within the water clusters and between the clusters and organic molecules, is examined. In particular, the structure of dmqd·6H2O contains a two-dimensional water sheet composed of pentagonal and octagonal units. Phqd·3H2O forms a hydrophilic extended structure encouraging the formation of one-dimensional chains consisting entirely of water. Both qd·2H2O and dmqd·2H2O can be considered to form one-dimensional chains, but only by utilising bridging carbonyl groups of the oxalamide moieties to form the extended array; if only the water is considered, zero-dimensional water tetramers are observed. The remaining hydrated structures, [Na+ dmqd-]dmqd·H2O, dmqd·1/3H2O and mqd·1/2H2O, all contain discrete water molecules but do not form extended water structures.

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Quinoxaline – Wikipedia,
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Evaluation of quinoxaline compounds as ligands of a site adjacent to S2 (AS2) of cruzain

The binding of ten quinoxaline compounds (1?10) to a site adjacent to S2 (AS2) of cruzain (CRZ) was evaluated by a protocol that include a first analysis through docking experiments followed by a second analysis using the Molecular Mechanics-Poisson-Boltzmann Surface Area method (MM-PBSA). Through them we demonstrated that quinoxaline compounds bearing substituents of different sizes at positions 3 or 4 of the heterocyclic ring might interact with the AS2, particularly interesting site for drug design. These compounds showed docking scores (DeltaGdock) which were similar to those estimated for inhibitors that bind to the enzyme through non-covalent interactions. Nevertheless, the free binding energies (DeltaG) values estimated by MM-PBSA indicated that the derivatives 8?10, which bear bulky substituents at position 3 of the heterocycle ring, became detached from the binding site under a dynamic study. Surprisingly, the evaluation of the inhibitory activity of cruzipain (CZ) of some derivatives showed that they increase the enzymatic activity. These results lead us to conclude about the relevance of AS2 as a pocket for compounds binding site, but not necessarily for the design of anti-chagasic compounds.

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Novel alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate receptor antagonists: Synthesis and structure-activity relationships of 6-(1H- imidazol-1-yl)-7-nitro-2,3(1H,4H)-pyrido[2,3-b]pyrazinedione and related compounds

We have synthesized and evaluated azaquinoxalinediones 3a-c for their activity in inhibiting [3H]AMPA binding from rat whole brain. It was found that the azaquinoxalinedione nucleus functions as a bioisostere for quinoxalinedione in AMPA receptor binding. The detailed structure-activity relationships of 6- and/or 7-substituted 2,3(1H,4H)-pyrido[2,3- b]pyrazinedione derivatives 4, 7-10, 13, 15, and 16 showed some differences in comparison with those of the corresponding substituted quinoxalinediones, including 6-(1H-imidazol-1-yl)-7-nitro-2,3(1H,4H)-quinoxalinedione (1) (YM90K). The X-ray study exhibited that conformation of the 7-nitro group of 1 · HCl was nearly coplanar with the quinoxaline ring, whereas the 6- imidazol1-yl group was rotated with respect to the aromatic ring. From the glycine site on NMDA receptor binding study, it is indicated that bulkiness of 6-substituents on pyridopyrazinediones may be responsible for the selectivity against the glycine site. Among the series of azaquinoxalinediones, 6-(1H-imidazol-1-yl)-7-nitro-2,3(1H,4H)-pyrido[2,3- b]pyrazinedione (8c) exhibited a combination of the best affinity to the AMPA receptors with a K(i) value of 0.14 muM and selectivity against the glycine site (no affinity at 10 muM). In vivo, 8c also protected against sound- induced seizure in DBA/2 mice (minimum effective dose, 10 mg/kg ip).

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SYNTHESIS AND PROPERTIES OF SOME DERIVATIVES OF 3,4-DIHYDRO-3-OXO-2-QUINOALINYLACETIC ACID

The paper desribes opening of isoxazole ring with 1,2-diaminobenzene leading to 2-cyanomethylene-3-oxo-1,2,3,4-tetrahydroquinoxaline and preparation of its derivatives.Synthesis has been studied of substituted 3,4-dihydro-3-oxo-quinoxaline-oxides, and tautomers of 1-oxides of 2-ethoxycarbonylmethylquinoxalines have been obtained.

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Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.

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Synthesis of Novel Substituted Phenyl-3-Hydrazinyl-Quinoxaline-2-Amine Derivatives: Evaluation of Antimicrobial Activity and Its Molecular Docking Studies

New series of quinoxaline derivatives (4a?4h) were synthesized by treating 2-chloro-3-hydrazinyl quinoxalin (3) with various anilines. Compound 3 was obtained from the 2,3-dichloroquinoxaline 2 which was prepared from 4-dihydroquinoxaline-2,3-dione (1). All synthesized compounds (4a?4h) were characterized by various spectral techniques, that is, IR, 1H-NMR, mass spectroscopy, and elemental analysis and completion of reaction were confirmed by TLC. In vitro antimicrobial activity of synthesized compounds was evaluated using disc diffusion assay against gram-positive and gram-negative microbial strains, and then, the minimum inhibitory concentration and IC50 values of compounds were also determined. The results of antimicrobial study revealed that compounds 4e, 4g, and 4a were active and exhibited better inhibitory activities as compared with standard drug amoxicillin. Docking studies were performed by using Argus lab, and all the compounds exhibited good docking scores between ?9.53 and ?7.94?kcal/mol against dihydrofolate reductase protein fragment from Staphylococcus aureus (PDB ID-4XE6). Among all compounds, 4e has shown the maximum docking score and found in agreement to in vitro studies.

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Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones and the use thereof as glycine receptor antagonist

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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