Brief introduction of 2-Chloro-3-methylquinoxaline

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Synthesis and characterization of polyaromatic azine derivatives of (eta5-C5H5) Fe(CO)2 and (eta5-C9H7) Fe(CO)2

The synthesis and characterization of 14 monometallic derivatives of quinoline, quinoxaline, quinazoline and tetraazolo<1,5-A>quinoline and a bimetallic derivative of quinoxaline are reported. These species were prepared in 11 to 88% isolated yields by metathesis reactions between NaFp or NaFp? (where Fp = (eta5 – C5H5)Fe(CO)2 and Fp? = (eta5 – indenyl)Fe(CO)2 ) and the appropriate chlorine substituted polyaromatic azines. These reactions are highly regioselective and generally produce a single organometallic product having the organometallic substituent(s) bonded to the more highly activated azine ring. The structures of three representative examples were confirmed by their X-ray crystal structures, which are reported for the title complexes 4-[(eta5-cyclopentadienyl)irondicarbonyl]-7-chloroquinoline (C16H10ClFeNO2; a = 7.608(1)A, b = 12.006(1)A, c = 15.664(1)A, V = 1431A3; orthorhombic; P212121; Z =4), 2-[(eta5-cyclopentadienyl)irondicarbonyl]-3-chloroquinoxaline (C15H9ClFeN2O2; a = 15.291(3) A, b = 6.561(2) A, c = 14.541(4) A, beta = 106.891(21), V= 1395.9A3; monoclinic; P21/c; Z = 4), and 2-[(eta5-indenyl)irondicarbonyl]-3-chloroquinoxaline (C19H11ClFeN2O2; a = 19.131(2)A, b = 6.688(1)A, c = 13.515(2) A, beta= 101.569(11), V = 1694.1 A3; monoclinic; P21/c; Z = 4). The bimetallic quinoxaline derivative 2,3-[(C5H5)2Fe2(CO)4]-quinoxaline has orrto-substituted organometallic groups and the spectroscopic data suggest that it has an unusual structure in solution, perhaps involving bridging cyclopentadienyl and carbonyl ligands.

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Quinoxaline chemistry. Part 6. Synthesis and evaluation of antiulcer and gastroprotective activity of 2-[arylmethylmercapto-,arylmethylsulfinyl-,piperazinyl-3-R-substituted ]quinoxalines

Thirty compounds possessing quinoxaline structure bearing either substituted arylmethylmercapto-, arylmethylsulfinyl group or a piperazinyl moiety in position 2 were prepared in order to evaluate an antiulcer and gastroprotective activity in rat pylorus ligature, in comparison with omeprazole and ranitidine at the dose of 100 mg/kg after oral administration. Among the compounds of the first group one third showed a moderate activity being about half potent as omeprazole whereas in the second group compound 5b exhibited an activity superior to that of ranitidine accompanied with the lowest incidence of lesions and mortality and another compound (5i) was equiactive as ranitidine.

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Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a] quinoxaline derivatives as inhibitors of the human protein kinase CK2

Herein we describe the synthesis and properties of substituted phenylaminopyrrolo[1,2-a]quinoxaline-carboxylic acid derivatives as a novel class of potent inhibitors of the human protein kinase CK2. A set of 15 compounds was designed and synthesized using convenient and straightforward synthesis protocols. The compounds were tested for inhibition of human protein kinase CK2, which is a potential drug target for many diseases including inflammatory disorders and cancer. New inhibitors with IC50 in the micro- and sub-micromolar range were identified. The most promising compound, the 4-[(3-chlorophenyl) amino]pyrrolo[1,2-a]quinoxaline-3-carboxylic acid 1c inhibited human CK2 with an IC50 of 49 nM. Our findings indicate that pyrrolo[1,2-a]quinoxalines are a promising starting scaffold for further development and optimization of human protein kinase CK2 inhibitors.

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Fragment based design of new H4 receptor-ligands with anti-inflammatory properties in vivo

Using a previously reported flexible alignment model we have designed, synthesized, and evaluated a series of compounds at the human histamine H 4 receptor (H4R) from which 2-(4-methyl-piperazin-l-yl)- quinoxaline (3) was identified as a new lead structure for H4R ligands. Exploration of the structure-activity relationship (SAR) of this scaffold led to the identification of 6,7-dichloro 3-(4-methylpiperazin-l-yl) quinoxalin-2(1H)-one (VUF 10214, 57) and 2-benzyl-3-(4-methyl-piperazin-l-yl) quinoxaline (VUF 10148, 20) as potent H4R ligands with nanomolar affinities. In vivo studies in the rat reveal that compound 57 has significant anti-inflammatory properties in the carrageenan-induced paw-edema model.

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FUSED BICYCLIC HETEROAROMATIC DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted heteroaromatic compounds containing two fused six- membered rings,tivity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

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Design, synthesis and anticancer properties of IsoCombretaQuinolines as potent tubulin assembly inhibitors

The synthesis and evaluation of a new series of IsoCombretaQuinolines (IsoCoQuines) 2 with a 2-substituted-quinoline in place of the 3,4,5-trimethoxyphenyl ring present in isoCA-4 and CA-4 are described. Most of these compounds displayed a potent cytotoxic activity (IC50< 10 nM) against a panel of five human cancer cell lines and inhibited tubulin assembly at a micromolar level. The most potent analogue 2b, having a 3-hydroxy-4-methoxyphenyl as B-ring, led to cell cycle arrest in G2/M phase. Docking studies indicate that 2b showed a binding mode comparable to those previously observed with quinazoline analogous (IsoCoQ) and with isoCA-4 at the colchicine binding site of tubulin. If you are interested in 32601-86-8, you can contact me at any time and look forward to more communication. Recommanded Product: 32601-86-8

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Synthesis and antimicrobial activity of 2-substituted benzyl hydrazino-3-methyl quinoxalines

Reduction of 3-methyl-2-(arylidcne hydrazino)quinoxalines 5a-1 with NaBH4 in controlled experimental conditions to give the 2-substituted benzyl hydrazine-3-methyl quinoxalines 6a-l have been described. The structure of compounds 6a-l have been confirmed from elemental analysis, IR, 1H NMR and mass spectral data. All the compounds have been screened for their antimicrobial activity against several microbes.

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Synthesis of some new 4-styryltetrazolo[1,5-a]quinoxaline and 1-substituted-4-styryl[1,2,4]triazolo[4,3-a]quinoxaline derivatives as potent anticonvulsants

4-Methyltetrazolo[1,5-a]quinoxaline (3) was prepared by the azide cyclocondensation of 2-chloro-3-methylquinoxaline (2). The reaction of 3 with aromatic aldehydes furnished 4-styryltetrazolo[1,5-a]quinoxalines (4a-f). Compound 2, on treatment with hydrazine hydrate gave 2-hydrazino-3-methylquinoxaline (5). The ring closure of 5 was achieved by the reaction of orthoesters and trifluoroacetic acid to yield 4-methyl-1-(substituted)[1,2,4]triazolo[4,3-a]quinoxalines (7a-c). Further, reaction of 7a-c with different aromatic aldehydes furnished the title compounds, 4-styryl-1-(substituted)[1,2,4]triazolo[4,3-a]quinoxalines (8a-i) in good yield. In another scheme, the hydrazino compound 5 was treated with different aromatic aldehydes to yield corresponding N-arylidenehydrazino quinoxalines (6a-d). Further, the oxidative cyclization of hydrazones by nitrobenzene yielded 1-aryl-4-methyl[1,2,4]triazolo[4,3-a]quinoxalines (7d-g), which on condensation with aromatic aldehydes gave the title compounds, 1-aryl-4-styryl[1,2,4]triazolo[4,3-a]quinoxalines (8j-u). The newly synthesized compounds have been characterized by FTIR, 1H NMR, 13C NMR and mass spectral data, followed by elemental analysis. Some of the compounds were screened for in vivo anticonvulsant activity. Few of them exhibited promising results.

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Synthetic profiles to pyrazolylquinoxalines

[Figure not available: see fulltext.] Pyrazolylquinoxalines act as important intermediates for the production of novel derivatives with potential biological applications. The current review covers the synthesis of 2(3)-(pyrazol-1(3(5),4)-yl)quinoxalines published from 1978 until present.

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