Top Picks: new discover of Quinoxaline-2,3(1H,4H)-dione

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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 quinoxaline derivatives from substituted acetanilides through intramolecular quaternization reactions

The cyclization of 2-dialkylamino-2?-halogeno- and 2-chloro-2?-(dialkylamino)acetanilides to quinoxaline derivatives has been studied in detail. These reactions proceed, respectively, through intramolecular aromatic nucleophilic or aliphatic nucleophilic substitution reactions and depending on the substituents and the experimental conditions, they lead to 3-oxoquinoxalinium salts or, after an alkyl chloride elimination, to quinoxalin-2-ones. Some new cases of the little known intramolecular quaternization of tertiary amines with aryl halides are described.

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A Combination of Visible-Light Organophotoredox Catalysis and Asymmetric Organocatalysis for the Enantioselective Mannich Reaction of Dihydroquinoxalinones with Ketones

An enantioselective photooxidative Mannich reaction of dihydroquinoxalinones with ketones by the merger of organophotoredox and asymmetric organocatalysis is described. This protocol features very mild reaction conditions using simple and cheap catalysts (Eosin Y and (S)-Proline) for the synthesis of chiral quinoxaline derivatives with good to high yields (up to 94%) and excellent enantioselectivities (up to 99% ee).

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ANTI-HCMV COMPOSITIONS AND METHODS

Novel compounds useful for treating and/or preventing HCMV infections are provided.

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More research is needed about 59564-59-9

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Electrochemical reduction of quinoxalino<2,3-b>quinoxaline: a revised mechanism

The electrochemical reduction of fluoflavine 2 gives compound 9 to which we had previously assigned a hexahydro-quinoxalino<2,3-b>quinoxaline structure.A crystallographic study of a diacetylated derivative of 9 shows that 9 is in fact 2-(o-aminoanilinomethyl)benzimidazole.This result permits us to propose a detailed reduction mechanism for 2 and its diacetyl derivative 25.

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Properties and Exciting Facts About 2,3-Dichloroquinoxaline

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Design and discovery of novel quinoxaline derivatives as dual DNA intercalators and topoisomerase II inhibitors

Backgroun/Methods: In attempt to develop new potent anti-tumor agents, a series of quinoxaline derivatives was designed and synthesized. The novel compounds were tested in vitro for their anti-proliferative activities against HePG-2, MCF-7 and HCT-116 cell lines. Additionally, DNA binding affinities as well as DNA-top II inhibitory activities of the synthesized compounds were investigated as potential mechanism for anticancer activity. Compounds 13, 15, 16 and 19 exhibited good cytotoxicity activities against the three cell lines (IC50 ranging from 7.6 to 32.4 muM) comparable to that of doxorubicin (IC50 = 9.8 muM). Results: Interestingly, the results of DNA binding and DNA-top II inhibition assays were in agreement with those of the cytotoxicity tests, where the most potent anticancer compounds showed good DNA binding affinities (IC50 ranging from 25.1 to 32.4 muM) and DNA-top II inhibitory activities (IC50 ranging from 6.4 to 15.3 muM) comparable to those of doxorubicin (IC50 = 28.1 and 3.8 muM, respectively). Furthermore, molecular docking studies were carried out for the new compounds in order to investigate their binding pattern with the prospective target, DNA-top II complex (PDB-code: 3qx3).

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Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders

We report the synthesis and structure-activity relationships of a class of tetracyclic butyrophenones that exhibit potent binding affinities to serotonin 5-HT2A and dopamine D2 receptors. This work has led to the discovery of 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3?,4?:4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl) -1-(4-fluorophenyl)-butan-1-one 4-methylbenzenesulfonate (ITI-007), which is a potent 5-HT2A antagonist, postsynaptic D2 antagonist, and inhibitor of serotonin transporter. This multifunctional drug candidate is orally bioavailable and exhibits good antipsychotic efficacy in vivo. Currently, this investigational new drug is under clinical development for the treatment of neuropsychiatric and neurological disorders.

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Properties and Exciting Facts About 2-Chloro-3-methylquinoxaline

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Discovery of new hit-molecules targeting Plasmodium falciparum through a global SAR study of the 4-substituted-2-trichloromethylquinazoline antiplasmodial scaffold

From 4 antiplasmodial hit-molecules identified in 2-trichloromethylquinazoline series, we conducted a global Structure-Activity relationship (SAR) study involving 26 compounds and covering 5 molecular regions (I ? V), aiming at defining the corresponding pharmacophore and identifying new bioactive derivatives. Thus, after studying the aniline moiety in detail, thienopyrimidine, quinoline and quinoxaline bio-isosters were synthesized and tested on the K1 multi-resistant P.?falciparum strain, along with a cytotoxicity evaluation on the human HepG2 cell line, to define selectivity indecies. SARs first showed that thienopyrimidines and quinolines were globally more cytotoxic, while quinoxaline analogs appeared as active as- and less cytotoxic than their quinazoline counterparts. Such pharmacomodulation in quinoxaline series not only provided a new antiplasmodial reference hit-molecule (IC50?=?0.4?muM, selectivity index?=?100), but also highlighted an active (IC50?=?0.4?muM) and quite selective (SI?=?265) synthesis intermediate.

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Synthesis, in vitro antitubercular activity and 3D-QSAR of novel quinoxaline derivatives

Twenty new quinoxalines bearing azetidinone and thiazolidinone groups were synthesized by cyclocondensation of Schiff bases of quinoxaline-2, 3-dione and were characterized with several analytical tools. They were tested against Mycobacterium tuberculosis H37Rv at a concentration of 10mug/mL by Microplate Alamar Blue Assay method. Quinoxaline derivatives with 2-chloro, dimethylamino and nitro substitutions exhibited in vitro activity, comparable to that of the drug, isoniazid. Three-dimensional quantitative structure-activity relationship studies indicated that electrostatic and steric field descriptors could explain the observed activity. The developed model fits the data well and has good predictive capability (r2=0.81, q2=0.71, F=27.06, r2_pred =0.84, r2m =0.84, r2 BS=0.80). Electronegative groups play an important role in the antitubercular activity.

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Archives for Chemistry Experiments of 2,3-Dichloroquinoxaline

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Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same

The present invention refers to organic electro corrosion inhibitor, and water including relates to organic electroluminescence device. The present invention according to organic electroluminescent compounds purity, solubility and as well as good heat stability, whose driving voltage is low, current efficiency and power it has significantly improved operating life a through hole is an organic electroluminescent device of high can be produced. (by machine translation)

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