Archives for Chemistry Experiments of 2,3-Dichloroquinoxaline

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Design, Synthesis and Cytotoxic Evaluation of Novel Chalcone Derivatives Bearing Triazolo[4,3-a]quinoxaline Moieties as Potent Anticancer Agents with Dual EGFR Kinase and Tubulin Polymerization Inhibitory Effects

A series of hybrid of triazoloquinoxaline-chalcone derivatives 7a?k were designed, synthesized, fully characterized, and evaluated for their cytotoxic activity against three target cell lines: human breast adenocarcinoma (MCF-7), human colon carcinoma (HCT-116), and human hepatocellular carcinoma (HEPG-2). The preliminary results showed that some of these chalcones like 7b?c, and 7e?g exhibited significant antiproliferative effects against most of the cell lines, with selective or non-selective behavior, indicated by IC50 values in the 1.65 to 34.28 muM range. In order to investigate the mechanistic aspects of these active compounds, EGFR TK and tubulin inhibitory activities were measured as further biological assays. The EGFR TK assay results revealed that the derivatives 7a?c, 7e, and 7g could inhibit the EGFR TK in the submicromolar range (0.093 to 0.661 muM). Moreover, an antitubulin polymerization effect was noted for the active derivatives compared to the reference drug colchicine, with compounds 7e and 7g displaying 14.7 and 8.4 micromolar activity, respectively. Furthermore, a molecular docking study was carried out to explain the observed effects and the binding modes of these chalcones with the EGFR TK and tubulin targets.

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Synthesis and antibacterial activity of fused 1,2,4-triazolo[4,3-a]quinoxaline and oxopyrimido[2?,1?:5,1]-1,2,4-triazolo[4,3-a]quinoxaline derivatives

A new series of potential antibacterial agents having tricyclic 1,2,4-triazolo-[4,3-a]quinoxaline fused with one or more heterocyclic rings was synthesized via several routes. The tricyclic 1-amino-4-chloro-1,2,4-triazolo[4,3-a]quinoxaline (2) and tetracyclic 1,6-diamino-bis-1,2,4-triazolo[4,3-a:3,4-c]quinoxaline (3) were synthesized from 2,3-dichloroquinoxaline (1) with two or four equivalents of thiosemicarbazide, respectively. Compound 2 was allowed to react with different aldehydes, alkoxides, cyclic amines, phenyl isothiocyanate, and t-butyl isocyanate to afford the corresponding quinoxaline derivatives. Moreover, compound 2 reacted with hydrazine hydrate to give compound 4 which was cyclized by carbon disulfide in alcoholic potassium hydroxide to give the tetracyclic compound 5. Compound 2 was subjected to another cyclocondensation reaction using diethyl ethoxymethylene malonate (DEMM), dimethyl acetylenedicarboxylate (DMAD), and ethyl cyanoacetate to give the tetracyclic compounds 18, 20, and 21, respectively. All the synthesized compounds were evaluated in vitro for antibacterial activity; compounds 18 and 20 were found to display the greatest antibacterial activities. Structural identification was provided by elemental analyses, IR, and 1H-NMR spectroscopy.

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Antiulcer compounds having a substituted alkynyl or quinoxaline nucleus and methods of making thereof

This invention relates to a novel compound which is useful as a drug in preventing and/or treating peptic ulcer-related diseases, to a production process thereof and to a pharmaceutical composition containing the same. Particularly, it provides a compound which has a specified substituted alkynylpyrazine nucleus or a specified substituted alkynylquinoxaline nucleus, represented by the following formula (I) STR1 wherein A is represented by the following formula (II) or (III) STR2 and R1 is represented by the following formula (IV), STR3 and the salts thereof, a production process thereof and a pharmaceutical composition containing the same. The inventive compound is useful as a drug in preventing and/or treating peptic ulcer-related diseases.

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The chemistry and applications of the quinoxaline compounds

The quinoxaline derivatives are beneficial compounds because of their various medicinal and industrial applications. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap. There are many reported procedures for the synthesis of bis- and polyquinoxalines and quinoxaline-containing macrocycles. The quinoxaline-based compounds as fascinating structures are important subjects of interest in either basic or applied sciences. This review summarizes the latest progresses related to the quinoxalines, quinoxaline-containing macrocycles, and bis- and poly quinoxalines, including the synthesis, functionalization and modification methods and applications of these compounds.

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Silver(I), nickel(II) N-heterocyclic carbene complexes based on bidentate bis-imidazolium salt with a quinoxaline linker: syntheses, structures, and characterization

Quinoxaline-bridged bidentate bis-imidazolium dicarbene ligand 1,1?-(quinoxaline-2,3-diyl)bis(3-methyl-1H-imidazol-3-ium) hexafluorophosphate salt H2L¡¤2PF6 (3) was prepared by a two-step reaction based on 2,3-bis(imidazol-1-yl)quinoxaline (1). First, the 2,3-bis(imidazol-1-yl)quinoxaline reacted with CH3I resulting in the 1,1?-(quinoxaline-2,3-diyl)bis(3-methyl-1H-imidazol-3-ium) iodide salt H2L¡¤2I (2), then through anion exchange reactions with NH4PF6 in water produced the desired bis-imidazolium bidentate ligand H2L¡¤2PF6 (3). Reaction of the bidentate bis-imidazolium ligands H2L¡¤2PF6 (3) with Ag2O in acetonitrile gave the macrocyclic binuclear silver(I) carbene complex [Ag2(L)2]¡¤2PF6¡¤CH3CN (4). Nickel carbene complex [Ni(L)PPh3Cl]¡¤PF6¡¤2DMSO (5) was obtained via transmetalation of 4 with Ni(PPh3)2Cl2 in DMSO. The bidentate carbene ligand is a chelating ligand in 5, while bridging in 4. The imidazolium ligand H2L¡¤2PF6 (3) and transition metal carbene complexes 4 and 5 have been fully characterized by elemental analysis, NMR, ESI-MS spectroscopy, and X-ray diffraction analyses. Furthermore, the UV and luminescent properties of 3?5 were also studied.

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Highly fluorescent heterocycles based on pyrazino fused 1,4,5,8-tetraazafulvalenes

Some new pyrazino-fused 1,4,5,8-tetraazafulvalenes of type (3-5) were synthesized and their structures were confirmed by IR, UV-VIS, 1H NMR spectra and elemental analysis. The X-Ray crystal structure analysis of a single crystal of derivative (3c) revealed a nearly ideal planarized heterofulvalene subunit. The new prepared tricyclic tetraazafulvalenes of type (3) show strong red fluorescence at 605 nm.

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AMINO-QUINOXALINE AND AMINO-QUINOLINE COMPOUNDS FOR USE AS ADENOSINE A2A RECEPTOR ANTAGONISTS

Compounds of the Formula (I), where W represents CH or N; and Q represents -CN, -C(=NOH)NH2, -CONHR1 or various herein described heterocyclic radicals; as well as pharmaceutically acceptable salts, solvates, esters and prodrugs thereof are adenosine A2a receptor antagonists and, therefore, are useful in the treatment of central nervous system diseases, in particular Parkinson”s disease.

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Organic compound and organic electroluminescent device containing the same (by machine translation)

The invention relates to a compound, which is characterized by, having a structural formula (1) as shown in a formula : In-flight, R1 -R9 Aryl or H, heteroaryl, C1-C10, each independently selected from alkenyl, C2-C10 of alkyl, C6-C30 of C3-C30 cyano ;R3 AND R4 Phenyl ring fused, R optionally linked to ring and carbazole9 A group fused ;X optionally and linked thereto is selected from the group consisting of O, S, CR ? R” or NR” ? ;R ?, R” and R” ? independently selected from the group C1-C10 alkyl, C3-C20 aryl or heteroaryl ;Y, respectively. 1 -Y4 Each independently selected from C, CH or N, wherein Y1 -Y4 A case of C is R. 9 An integer CH in which H;L in, C3-C20 selected from a single bond, C3-C20 or an arylene group, C3-C20 and an integer, C3-C20 of the heteroarylene ;m substituted with a tetrasubstituted aryl or heteroaryl 0-4 of, n is preferably an integer of 1 – 4, and preferably, is an integer n of 1 – 2, and the present invention also relates to an organic electroluminescent device, containing the compound. (by machine translation)

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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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Aryl-aryl bonds formation in pyridine and diazine series. Diazines part 41

The synthesis of several symmetrical polyaromatic compounds with pyridine or diazine units has been achieved by homocoupling of aryl halides with Pd(OAc)2 as catalyst. Cross-coupling reactions of aryl Grignard reagents with Fe(acac)3 as catalyst allowed the synthesis of various unsymmetrical polyaryl- or polyheteroaryl compounds with pi-deficient rings.

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