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Triarylamine-3- based quinoxaline-2- imidazolinamide derivative as well as preparation method and application thereof (by machine translation)

The preparation method and, the 3 – application of the diarylamine quinoxaline-3 – 2,formamide derivative disclosed by the invention have the advantages of 3 – high yield and low production cost, and the preparation method and, the application thereof have a high medical value and 3 – a wide market prospect. (by machine translation)

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Novel Antagonists of 5-HT3 Receptors. Synthesis and Biological Evaluation of Piperazinylquinoxaline Derivatives

A series of piperazinylquinoxalines has been synthesized and studied as 5-HT3 receptor antagonists in different preparations.Antagonism to 5-HT in the longitudinal muscle of the guinea pig ileum was particularly prominent in cyanoquinoxaline derivatives with an alkyl substituent on the piperazine moiety.The pA2 of some selected compounds against the 5-HT3 agonist 2-methyl-5HT in the guinea pig ileum was in the range of tropisetron or ondansetron, and one of them, 7e, was more potent than these reference compounds by approximately 2 or 3 orders of magnitude.However, these compounds were markedly less potent than either tropisetron or ondansetron as displacers of 3H-BRL 43694 binding to rat cortical membranes or as antagonists of the Bezold-Jarisch reflex in rats.Piperazinylcyanoquinoxalines represent a new class of 5-HT3 antagonists with a selective effect on guinea pig peripheral receptors.

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Extended knowledge of Ethyl 3-chloroquinoxaline-2-carboxylate

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Novel imidazoquinoxalines

Novel imidazoquinoxalines of the formula STR1 wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, –NH4, alkali metal, alkaline earth metal, magnesium, aluminum and non-toxic, pharmaceutically acceptable amines, X is selected from the group consisting of hydrogen, alkoxy of 1 to 5 carbon atoms and carbamoyl and Y and Z are individually selected from the group consisting of hydrogen and halogen and their non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity and their preparation.

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QUINOLINE AND QUINAZOLINE AMIDES AS MODULATORS OF SODIUM CHANNELS

The invention relates to compounds of formula (I) or pharmaceutically acceptable salts thereof, useful as inhibitors of sodium channels: formula (I). The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders, including pain.

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Synthese de la benzopyranno<1><2,3-b>quinoxalinone-12

3-Benzyl-2-quinoxalinones were obtained by condensation of o-phenylenediamine with phenylpyruvic acids.These quinoxalinones were easily substituted in position 2 and which permitted the preparation of many derivatives, however, cyclisation of these compounds into 12H-<1>benzopyrano<2,3-b>quinoxalines failed.This new heterocycle might be syntesized from ethyl 2-phenoxy-3-quinoxalinecarboxylate.

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Synthesis of Cyano-Substituted Heterocycles by Means of Tetraethylammonium Cyanide

Chloropyrimidines 2, 3 and Chlorquinazolines 9, 10, after conversion into trimethylammonio derivatives 4, 5, 11, 12, react with tetraethylammonium cyanide 1a under very mild conditions to give pyrimidine carbonitriles 6, 7 and quinazoline carbonitriles 13, 14.Direct synthesis of quinoxaline carbonitriles 19 is possible by reaction of chloroquinoxalines 15, 18 with 1a.

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Ligand-based design, synthesis, and pharmacological evaluation of 3-methoxyquinoxalin-2-carboxamides as structurally novel serotonin type-3 receptor antagonists

Employing a ligand-based approach, 3-methoxyquinoxalin-2-carboxamides were designed as serotonin type-3 (5-HT3) receptor antagonists and synthesized from the starting material o-phenylenediamine in a sequence of reactions. The structures of the synthesized compounds were confirmed by spectral data. These carboxamides were investigated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparations from guinea-pig ileum against a standard 5-HT3 agonist, 2-methy-5-HT, and their antagonism activities are expressed as pA2 values. Compounds 6a (pA2: 7.2), 6e (pA2: 7.0), 6f (pA2: 7.5), 6g (pA2: 7.5), 6n (pA2: 7.0), and 6o (pA2: 7.2) exhibited antagonism greater than that of the standard 5-HT3 antagonist, ondansetron (pA2: 6.9).

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Pyrazolo[4?,3?:5,6]pyrano[2,3-b]quinoxalin-4(1H)-one: Synthesis and characterization of a novel tetracyclic ring system

(Chemical Equation Presented) Derivatives of the hitherto unknown ring system, pyrazolo[4?,3?:5,6]pyrano[2,3-b]quinoxalin-4(1H)-one, are synthesized in one step from the corresponding 1-substuituted or 1,3-disubstituted 2-pyrazolin-5-ones and 3-chloroquinoxaline-2-carbonyl chloride using calcium hydroxide in boiling 1,4-dioxane. The parent system carrying no substituent in positions 1 and 3 is obtained upon treatment of the 1-PMB (p-methoxybenzyl) protected congener with trifluoroacetic acid. Detailed NMR spectroscopic investigations including unambiguous chemical shift assignments of all 1H, 13C, and 15N resonances of the obtained tetracycles are reported.

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Synthesis of 2-(Quinoxalin-2-ylamino-benzotriazolyl) Pentanedioic Derivatives as Potential Anti-Folate Agents

Anti-folate agents had a significant impact on therapeutic treatment plans for diseases such as cancer, and bacterial and parasitic infections, notably malaria. Quinoxaline derivatives showed in vitro anticancer activity and were able to inhibit both the dihydrofolate reductase and thymidylate synthase. Here, we decided to combine the chemical properties of quinoxalines and quinoxaline 1,4-dioxides with those of benzotriazole nucleus with the aim to evaluate the resulting biological properties. Two main new series, including more than 60 compounds, were prepared. In the first one, the benzotriazole moiety was linked through the nitrogen atoms 1, 2, or 3, to a glutaric acid substituent to simulate a glutamic moiety. In the second series, the glutaric acid was substituted with acetic acid moiety to evaluate the effects of steric hindrance. Here, we describe the multistep chemical processes to obtain all titled quinoxalines starting from commercially available diamines. The classical oxidation of selected quinoxalines was unsuccessful, and we have come to an independent synthetic pathway to obtain new derivatives linked to the benzotriazole moieties starting from synthons bearing N-oxide functionality.

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Quinoxaline chemistry. Part XVII. Methyl [4-(substituted 2-quinoxalinyloxy) phenyl] acetates and ethyl N-{[4-(substituted 2-quinoxalinyloxy) phenyl] acetyl} glutamates analogs of methotrexate: Synthesis and evaluation of in vitro anticancer activity

Fourteen out of 21 quinoxaline derivatives described in the present paper were selected at NCI for evaluation of their in vitro anticancer activity. Preliminary screening showed that some derivatives exhibited a moderate to strong growth inhibition activity on various tumor panel cell lines between 10-5 and 10-4 M concentrations. Interesting selectivities were also recorded between 10-8 and 10-6 M for the compounds 9 and 13.

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