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The invention belongs to the field of pharmaceutical chemistry, in particular relates to a toll-like receptor regulation has the effect of a compound, its preparation and use. The present invention provides a compound of the following formula X shown. The compounds of formula X can be used as the toll-like receptor modulators, its activity is high. In addition, compounds of the invention have high efficiency and low toxicity, anti-drug resistance and the like, it has clinical application value. And, the compounds of the invention of simple synthesis steps, therefore with greater economic value. (by machine translation)

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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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The electrochemical oxidation of phenols and their alkyl ethers not containing strong electron-withdrawing substituents in fluorosulfonic acid takes place in the form of the benzenonium ions and is irreversible in character.With the introduction of substituents of the -M type into the benzene ring the oxidation process affects the unprotonated molecules to a first approximation and in many cases goes reversibly to the radical-cations.Comparison of the oxidation potentials of the substrates in acetonitrile and fluorosulfonic acid made it possible to reveal certain characteristics of the fine structure of these radical-cations, which is determined by the ability of the latter to interact with the medium.Heterocyclic cations whose oxidation potentials in acetonitrile lie beyond the limit of the discharge of the supporting electrolyte can be oxidized in fluorosulfonic acid.Cations of the quinolinium, isoquinolinium, acridinium, acridizinium, imidazolium, and other series, which have irreversible many-electron waves in acetonitrile, give well-defined reversible peaks for oxidation to the corresponding radical-dications in fluorosulfonic acid.In phenyl- and benzyl-substituted cations the substituents and not the positively charged heterocycle itself can undergo oxidation.

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Nucleophilic aromatic substitution (SNAr) is a class of reaction that has become very important over time. This type of transformation usually proceeds without the use of metal catalysts, making it very important for pharmaceutical and industrial purposes. Nevertheless, in order to obtain the desired substituted product, activated substrates are required to allow SNAr reactions under mild conditions. In this context, quinoxaline derivatives are one class of N-heteroarenes that has attracted great attention from the scientific community because of the large variety of applications for their derivatives in many fields, such as biological and technological areas. There are several reported methods for the synthesis of quinoxaline derivatives. Nonetheless, reactions of 2,3-dichloroquinoxaline (DCQX) with nucleophilic species has become a viable alternative because of the possibility to form new carbon-heteroatom bonds (e.g. C[sbnd]O, C[sbnd]N, and C[sbnd]S) directly at C2 and/or C3 positions of the quinoxaline moiety. This current review brings an overview of the last decade on the remarkable versatility of DCQX as a substrate for SNAr reactions. Herein, we show several examples in which DCQX reacts with N-, O-, S-, P- and C-nucleophiles, including controlled processes for the selective formation of mono- and disubstituted substrates. Almost all polyfunctionalized quinoxalines synthesized using this approach have shown applications in different areas such as in biological and technological fields.

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

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Drug candidates for inhibition of HIV-I replication can target Src family kinases (SFK), such as Hck, that interact with Nef protein of the virus. Compounds characterized by such inhibitory activity were identified via an assay for kinase activity of an SFK in a Nef:SFK complex. Illustrative of inhibitors identified using the kinase assay are various 2,3- diaminoquinaxolines and furo[2,3-d]pyrimidines. The inventive inhibitors were found to arrest HIV-I viral replication in vitro.

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A new approach to selected 1,2,4-benzotriazines has been developed. 3,3,6,6-Tetrachloro-1,2-cyclohexanedione reacted with 2-pyridylamidrazones to give unexpected isolable bishemiaminal intermediates instead of the corresponding ketodiazenes. Subsequent dehydration gave 5,5,8,8-tetrachloro-3- (2-pyridyl)-5,6,7,8-tetrahydrobenzo[e][1,2,4]triazines, which were converted into previously unknown 5,8-dichloro-3-(2-pyridyl)benzo[e][1,2,4]triazines by dehydrochlorination under basic conditions. Severe limitations of reactions between o-benzoquinones with amidrazones have been circumvented in this manner. This preparative process has also been adapted to a one-pot protocol.

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Excited-state second protonation of 2-aminoquinoxaline occurs in aqueous perchloric acid at a rate of 1.1×1010 L.mol-1.s-1.The reaction is very sensitive to solvent structure and is blocked in acidic poly(vinyl alcohol) and heptane solutions of trifluoroacetic acid.Calculations of effective valence electron potentials provide a good reactivity index for pKa changes in excited 2-aminoquinoxaline and 2,3-diaminoquinoxaline.

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Three new alpha,alpha?-diimine ligands were synthesized based on condensation of 1,10-phenanthroline-5,6-dione with 1,2-phenylenediamine derivatives using different approaches. All compounds were fully characterized by IR, 1H and 13C NMR, UV-visible, and MS spectroscopies. We report the first example of a dipyrido[3,2-f:2?,3?-h]quinoxalino[2,3-b]quinoxaline, which exhibits a strong absorption at 430 nm and an interesting electrochemical behavior. These new molecules may have biological potential and are of synthetic and technological importance.

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A new approach to selected 1,2,4-benzotriazines has been developed. 3,3,6,6-Tetrachloro-1,2-cyclohexanedione reacted with 2-pyridylamidrazones to give unexpected isolable bishemiaminal intermediates instead of the corresponding ketodiazenes. Subsequent dehydration gave 5,5,8,8-tetrachloro-3- (2-pyridyl)-5,6,7,8-tetrahydrobenzo[e][1,2,4]triazines, which were converted into previously unknown 5,8-dichloro-3-(2-pyridyl)benzo[e][1,2,4]triazines by dehydrochlorination under basic conditions. Severe limitations of reactions between o-benzoquinones with amidrazones have been circumvented in this manner. This preparative process has also been adapted to a one-pot protocol.

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