Archives for Chemistry Experiments of Quinoxaline-2,3-diamine

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New bisanthraquinone azomethine dyes

The present invention relates to novel colorants based on bisanthraquinone azamethine derivatives or their metal complexes for the mass coloring of polymers, either for polar polymers such as polyamides, polyesters, polycarbonates and ABS; or for non-polar polymers such as polyethylene and polypropylene.The novel colorants are characterized by i) a central substituted or unsubstituted annealed aromatic ring system comprising at least one heteroatom and ii) two anthraquinone moieties attached thereto by azamethine bridges.The novel colorants provide for excellent compatibility with the polymer substrate, excellent heat stability and light fastness.

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Searching for the Multi-Target-Directed Ligands against Alzheimer’s disease: Discovery of quinoxaline-based hybrid compounds with AChE, H 3R and BACE 1 inhibitory activities

A novel series of quinoxaline derivatives, as Multi-Target-Directed Ligands (MTDLs) for AD treatment, were designed by lending the core structural elements required for H3R antagonists and hybridizing BACE 1 inhibitor 1 with AChE inhibitor BYYT-25. A virtual database consisting of quinoxaline derivatives was first screened on a pharmacophore model of BACE 1 inhibitors, and then filtered by a molecular docking model of AChE. Seventeen quinoxaline derivatives with high score values were picked out, synthesized and evaluated for their biological activities. Compound 11a, the most effective MTDL, showed the potent activity to H3R/AChE/BACE 1 (H3R antagonism, IC50 = 280.0 ¡À 98.0 nM; H3R inverse agonism, IC50 = 189.3 ¡À 95.7 nM; AChE, IC50 = 483 ¡À 5 nM; BACE 1, 46.64 ¡À 2.55% inhibitory rate at 20 muM) and high selectivity over H1R/H2R/H4R. Furthermore, the protein binding patterns between 11a and AChE/BACE 1 showed that it makes several essential interactions with the enzymes.

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Exploration of quinoxaline derivatives as antimicrobial and anticancer agents

Novel 2 and 3-substituted quinoxaline derivatives were synthesized through various synthetic pathways, among which cyanoacetamide and cyanoacetohydrazide quinoxaline derivatives 4a-c and 11a-c, respectively, were synthesized. Furthermore, methoxy quinoxaline derivatives 3c and quinoxaline derivatives bearing substituted pyridines 6a,b, 12a,b, and 13a,b were designed to be synthesized. However, we have synthesized acrylohydrazide 5a,b and 7/acrylamide derivatives, Schiff base analogues 14a-f, pyrazole derivatives 15a-e, amide derivatives 16a-f, guanidine derivatives 16 g,h as well as, quinoxalin-2-methylallyl propionate derivative 14g. All the synthesized compounds were confirmed via spectral data and elemental analyses. Moreover, the newly synthesized compounds were evaluated for their antimicrobial activity (Gm +ve, Gm ?ve in comparison to Gentamycin a standard) and fungi (in comparison to Ketoconazole as a standard). Thus, compound 16b showed promising antimicrobial activity against B. subtilis, P. vulgaris, and S. mutants with values ranging from 20 to 27-mm zone of inhibition. While compounds 5a, 14e,f, and 16a,c,d,g,h showed potent antimicrobial activity. Moreover, the National Cancer Institute (NCI) selected 20 compounds that were submitted for anticancer screening against 60 types of cancer cell lines. The most active compounds are 5b and 12a where compound 5b containing 2,4-dichlorophenyl moiety at cyanoacetamide linkage of hydrazine quinoxaline backbone exerted significant growth inhibition activity against Leukemia MOLT-4, Renal cancer UO-31, and Breast cancer MCF-7. In addition, compound 12a having 4,6-diaminopyridinone side chain at position-3 of quinoxaline nucleus exhibited remarkable anticancer activity against renal cancer UO-31.

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Novel highly electron-deficient quinoxaline-annulated 1,3,2-diazagermol- and diazastannol-2-ylidenes, stabilized as LiCl adducts

Reaction of 2,3-bis(neopentylamino)quinoxaline (1) with nBuLi and GeCl4 or GeCl2¡¤(dioxane) (molar ratio 1:2:1) in THF furnished highly moisture-sensitive Ge(IV) and Ge(II) heterocycles 2a and 3a, respectively. The quinoxaline-annulated N-heterocyclic germylene (quinNHGe) 3a is stable only in the presence of Li(THF)x and exhibits electrophilic properties associated with the strongly electron-withdrawing annulation. Coordination of chloride at Ge(II) and of Li+ at nitrogen is assumed, as found in crystals of a bis(quinoxaline)-annulated eight-membered NHGe LiCl adduct. Addition of dineopentyl-benzimidazol-2-ylidene (bnNHC) provides a labile bnNHC-quinNHGe adduct 4 as indicated by strong downfield coordination shift of the NMR signal for the carbene donor atom. Attempts to grow single crystals led to decomposition and protonation of the carbene forming the bis(benzimidazolium) salt 5 with Li2 (THF)2 Cl42 – anion. Introduction of 2-methoxyethyl or 2-dimethylaminoethyl side arms as chelating functional groups into the diaminoquinoxalines 6 and 7 and subsequent reaction with 2 nBuLi/GeCl2¡¤(dioxane) did not markedly stabilize the resulting donor-substituted quinNHGe 8 and 9. Related silicon (2b) and tin heterocycles (3c) were synthesised for comparison. The quinoxaline-annulated N-heterocyclic stannylene 3c exhibits an extreme 119Sn upfield shift compared to other N-heterocyclic stannylenes, suggesting higher coordination at tin.

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Chemical and electrochemical reduction of pyrazino<2,3-b>quinoxalines

The hydrogenation of 2,3-dimethylpyrazino<2,3-b>quinoxaline 1 and 2-phenylpyrazino<2,3-b>quinoxaline 2 leads to the corresponding 5,10-dihydroderivatives 3b and 4b.LiAlH4 reduction of 2, of 2,3-dimethyl-6,7-diphenylpyrazino<2,3-b>pyrazine 8 and 2,6,7-triphenylpyrazino<2,3-b>pyrazine 9 furnishes the corresponding 1,2,3,4-tetrahydroderivatives 7, 10 and 11.NaBH4 reduction of 2 leads to a mixture of 4b and 7.In hydroorganic medium 1 and 2 are electrochemically reduced to 3b and 4b with which they form a redox system.

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On the Amination of Azaheterocycles. A New Procedure for the Introduction of an Amino Group

A new method of amination of diazines and triazines, using potassium amide, liquid ammonia and potassium permanganate, has been described.

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