Awesome Chemistry Experiments For Quinoxaline-2,3(1H,4H)-dione

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ESR-Untersuchungen an Thioamiden, 8. Radikalanionen der Imidazolidintrione, Piperazindione, Piperazintetraone und Chinoxalindione sowie ihrer Schwefel-Analoga.

Cyclische Oxamid-Derivate vom Typ des Imidazolidin-4,5-dions, Piperazin-2,3-dions, Piperazin-2,3,5,6-tetraons und Chinoxalin-2,3-dions sowie Thio-Analoga und mit 2H, 13C oder 15N markierte Vertreter werden dargestellt und durch in-situ-Elektroreduktion in die entsprechenden Radikalanionen uebergefuehrt.Aus deren isotropen und anisotropen ESR-Spektren sowie einer Analyse der Linienbreite und Linienform wird die Spindichteverteilung ermittelt und anhand MO-theoretisch berechneter Werte diskutiert.

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Quinoxaline – Wikipedia,
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Discovery and antiproliferative evaluation of new quinoxalines as potential DNA intercalators and topoisomerase II inhibitors

In continuation of our previous work on the design and synthesis of topoisomerase II (Topo II) inhibitors and DNA intercalators, a new series of quinoxaline derivatives were designed and synthesized. The synthesized compounds were evaluated for their cytotoxic activities against a panel of three cancer cell lines (Hep G-2, Hep-2, and Caco-2). Compounds 18b, 19b, 23, 25b, and 26 showed strong potencies against all tested cell lines with IC50 values ranging from 0.26 ¡À 0.1 to 2.91 ¡À 0.1 muM, comparable with those of doxorubicin (IC50 values ranging from 0.65 ¡À 0.1 to 0.81 ¡À 0.1 muM). The most active compounds were further evaluated for their Topo II inhibitory activities and DNA intercalating affinities. Compounds 19b and 19c exhibited high activities against Topo II (IC50 = 0.97 ¡À 0.1 and 1.10 ¡À 0.1 muM, respectively) and bound the DNA at concentrations of 43.51 ¡À 2.0 and 49.11 ¡À 1.8 muM, respectively, whereas compound 28b exhibited a significant affinity to bind the DNA with an IC50 value of 37.06 ¡À 1.8 muM. Moreover, apoptosis and cell-cycle tests of the most promising compound 19b were carried out. It was found that 19b can significantly induce apoptosis in Hep G-2 cells. It has revealed cell-cycle arrest at the G2/M phase. Moreover, compound 19b downregulated the Bcl-2 levels, indicating its potential to enhance apoptosis. Furthermore, molecular docking studies were carried out against the DNA?Topo II complex to examine the binding patterns of the synthesized compounds.

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Design, synthesis and structure-activity relationship of novel quinoxaline derivatives as cancer chemopreventive agent by inhibition of tyrosine kinase receptor

The cancer chemopreventive activity of quinoxaline derivatives 1-20 has been evaluated by studying the inhibitory effect on Epstein-Barr virus early antigen (EBV-EA) activation. The quinoxaline derivatives 1-20 showed inhibitory effect on EBV-EA activation without cytotoxicity on Raji cells. All compounds exhibited dose dependent inhibitory activities, most of them showed significant activity at 1000 mol ratio/12-O-tetradecanoylphorbol-13-acetate (TPA). Compounds 7 and 9 exhibited stronger inhibitory effects on the EBV-EA activation than that of the representative control, oleanolic acid, at the highest measured concentration. In addition, compounds 7-10 showed potent and selective inhibition of human tyrosine kinase (TRK) in liver cancer HepG2 and breast cancer MCF-7 cell lines similar to the positive control, doxorubicin.

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A quinoxalinone derivatives of structure, preparation method and use thereof (by machine translation)

The invention provides a quinoxalinone derivatives (compounds of formula I shown) structure, preparation method, and its pharmaceutically acceptable salt 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 removing free radicals, lipid peroxide and inhibit the active oxygen, thereby preventing and/or treating diabetes complication. (by machine translation)

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HMPA mediated one pot synthesis of 1-alkyl/aryl-4-dimethylamino[1,2,4]triazalo[4,3-a]quinoxalines

o-Phenylenediamine 1 is condensed with oxalic acid using Phillips’ procedure to obtain quinoxaline-2, 3-dione 2. The latter on treatment with hydrazine hydrate gives the known 2-hydrazinoquinoxalin -3-one 3. Reaction of 3 with various acid chlorides (which were obtained from the corresponding carboxylic acids by reaction with thionyl chloride in the presence of catalytic amount of dimethyl formamide) in HMPA medium at 220C in one pot reaction yield the corresponding 1-substituted-4-dimethylamino[1, 2, 4]triazolo[4, 3-a]quinoxalines 4. This reaction has been shown to proceed through the intermediacy of 2-(N-acyl/aryl hydrazinoquinoxalin -3-one 5 and 1-substituted-4-oxo-[1, 2, 4] triazolo[4, 3-a]quinoxalines 6. An interesting observation here has been that 5 can be cyclised to 6 at a considerably lower temperature of 100C than the requisite 220C using catalytic amount of HCl.

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The use of diethylene glycol in the synthesis of 2,2′-bibenzimidazole from o-phenylenediamine and oxalic acid

One- and two-step syntheses of 2,2′-bibenzimidazole were compared. Diethylene glycol was used as solvent that provides good solubility of the substrates. The limitation of the one-step preparation is the formation of the by-product, fluoflavine. The two-step synthesis proceeds with the separation of the intermediate product, 1,4-dihydroquinoxaline-2,3-dione, and the final product is only 2,2′-bibenzimidazole. The total yield of the two-step synthesis is above 85%.

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Design and synthesis of new quinoxaline derivatives as anticancer agents and apoptotic inducers

The quinoxaline scaffold is a promising platform for the discovery of active chemotherapeutic agents. Three series of quinoxaline derivatives were synthesized and biologically evaluated against three tumor cell lines (HCT116 human colon carcinoma, HepG2, liver hepatocellular carcinoma and MCF-7, human breast adenocarcinoma cell line), in addition to VEGFR-2 enzyme inhibition activity. Compounds VIId, VIIIa, VIIIc, VIIIe and XVa exhibited promising activity against the tested cell lines and weak activity against VEGFR-2. Compound VIIIc induced a significant disruption in the cell cycle profile and cell cycle arrest at the G2/M phase boundary. In further assays, the cytotoxic effect of the highly active compounds was determined using a normal Caucasian fibroblast-like fetal lung cell line (WI-38). Compound VIIIc could be considered as a lead compound that merits further optimization and development as an anti-cancer and an apoptotic inducing candidate against the HCT116 cell line.

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A new facile, efficient synthesis and structure peculiarity of quinoxaline derivatives with two benzimidazole fragments

A highly efficient and versatile method for the synthesis of quinoxaline derivatives with two benzimidazole fragments have been developed on the basis of the ring contraction of 3-(benzimidazo-2-yl)quinoxalin-2(1H)-one with 1,2-diaminobenzene and its various types of substituted and condensed derivatives. Owing to the inter- and intramolecular processes, involving self association, proton exchange, conformational, and/or tautomeric exchanges between several forms for most of the bis-benzimidazolylquinoxalines signals of bridged and neighboring carbon atoms and the hydrogen atoms of the neighboring carbon atoms of benzimidazole fragments in the NMR spectra are broadened. The conjugation between the benzimidazole fragments and the quinoxaline core of the molecules is increased from the quinoxaline derivative (10c) to its thiadiazol[f]- (17) and pyrrolo[a]-(19) annulated derivatives, resulting in a greater planarity of the molecule as a whole.

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Quinoxalines and drugs prepared therefrom

Quinoxaline-2,3-(1H,4H)-diones of the formula I STR1 and their tautomeric and enantiomeric forms and their physiologically tolerated salts, the variables R, R 1 and R 2 have the meanings specified in claim 1, and are useful for therapeutic treatment of neurodegenerative disorders, neurotoxic disturbances or as antiepileptics, antidepressants and anxiolytics; and drugs composed thereof.

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Synthesis and photochemical reaction of novel, visible-wavelength oxidizable polymerization sensitizer based on the 12H-quinoxalino[2,3-b][1,4]benzothiazine skeleton

Novel dyes based on the 12H-quinoxalino[2,3-b] [1,4]benzothiazine skeleton were synthesized and subsequently characterized using 1H NMR. Their electrochemical and spectral properties, such as absorption and emission spectra, quantum yield of fluorescence, and quantum yield of singlet oxygen formation, were measured. These compounds were evaluated as sensitizers for alkoxypyridinium salt photodecomposition, and the results are discussed on the basis of the free energy change for electron transfer from benzothiazine dyes to alkoxypyridinium compounds. Benzothiazine dyes are useful oxidizable sensitizers for N-alkoxypyridinium photoinitiators. The mechanism of the dye photobleaching is supported by time-dependent density functional theory (TD-DFT) calculations and the quantum yields of sensitized proton formation. Photoredox pairs consisting of benzothiazine dyes and alkoxypyridinium salt were found to be effective initiation systems for free radical polymerization of methyl acrylate and trimethylolpropane triacrylate (TMPTA) using visible light.

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