2213-63-0| Heterocyclic Building Blocks-quinoxaline

Etkind, Samuel I. et al. published their research in ACS Sustainable Chemistry & Engineering in 2022 | CAS: 2213-63-0

2,3-Dichloroquinoxaline (cas: 2213-63-0) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. Quinoxaline-1,4-di-N-oxide derivatives have shown to improve the biological results and are endowed with anti-viral, anti-cancer, anti-bacterial, and anti-protozoal activities with application in many other therapeutic areas.Synthetic Route of C8H4Cl2N2

Thianthrene-Based Bipolar Redox-Active Molecules Toward Symmetric All-Organic Batteries was written by Etkind, Samuel I.;Lopez, Jeffrey;Zhu, Yun Guang;Fang, Jen-Hung;Ong, Wen Jie;Shao-Horn, Yang;Swager, Timothy M.. And the article was included in ACS Sustainable Chemistry & Engineering in 2022.Synthetic Route of C8H4Cl2N2 This article mentions the following:

Bipolar redox activity is generally obtained using a single moiety that can be both oxidized and reduced or by tethering two distinct redox active mols., together with a covalent linker. Herein, we demonstrate an alternative approach using the SNAr and SNAr-type reactions of benzene-1,2-dithiols and electron-deficient aromatic halides or halogenated quinones to prepare a family of compact, thianthrene-based bifunctional mols. The potential of these mols. as electrolytes for redox flow batteries was assessed in static cells as a proof of concept. Cycling in a static cell demonstrated that the thianthrene-quinone, PQtBuTH (8), is highly stable, compared to other sym. organic active materials, with 44% capacity retention over 450 cycles (16.7 days), and an initial energy d. of 1.3Wh/L at a concentration of 0.1 M. Redox flow batteries represent a promising grid-scale energy storage technol., and the development of new sym. electrolyte systems in organic solvents can potentially mitigate issues associated with membrane crossover and provide high cell voltages. In the experiment, the researchers used many compounds, for example, 2,3-Dichloroquinoxaline (cas: 2213-63-0Synthetic Route of C8H4Cl2N2).

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ezzat, Hany G. et al. published their research in Molecular Diversity in 2021 | CAS: 2213-63-0

2,3-Dichloroquinoxaline (cas: 2213-63-0) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.Category: quinoxaline

Design, synthesis, and molecular docking studies of new [1,2,4]triazolo[4,3-a]quinoxaline derivatives as potential A2B receptor antagonists was written by Ezzat, Hany G.;Bayoumi, Ashraf H.;Sherbiny, Farag F.;El-Morsy, Ahmed M.;Ghiaty, Adel;Alswah, Mohamed;Abulkhair, Hamada S.. And the article was included in Molecular Diversity in 2021.Category: quinoxaline This article mentions the following:

Many shreds of evidence have recently correlated A2B receptor antagonism with anticancer activity. Hence, the search for an efficient A2B antagonist may help in the development of a new chemotherapeutic agent. In this article, 23 new derivatives of [1,2,4]triazolo[4,3-a]quinoxaline were designed and synthesized and its structures were confirmed by different spectral data and elemental analyses. The results of cytotoxic evaluation of these compounds showed six promising active derivatives with IC₅₀ values ranging from 1.9 to 6.4μM on MDA-MB 231 cell line. Addnl., mol. docking for all synthesized compounds was performed to predict their binding affinity toward the homol. model of A2B receptor as a proposed mode of their cytotoxic activity. Results of mol. docking were strongly correlated with those of the cytotoxic study. Finally, structure activity relationship analyses of the new compounds were explored. In the experiment, the researchers used many compounds, for example, 2,3-Dichloroquinoxaline (cas: 2213-63-0Category: quinoxaline).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Alsaif, Nawaf A. et al. published their research in Bioorganic Chemistry in 2021 | CAS: 2213-63-0

2,3-Dichloroquinoxaline (cas: 2213-63-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB),One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene.Computed Properties of C8H4Cl2N2

New quinoxaline derivatives as VEGFR-2 inhibitors with anticancer and apoptotic activity: design, molecular modeling, and synthesis was written by Alsaif, Nawaf A.;Dahab, Mohammed A.;Alanazi, Mohammed M.;Obaidullah, Ahmad J.;Al-Mehizia, Abdulrahman A.;Alanazi, Manal M.;Aldawas, Saleh;Mahdy, Hazem A.;Elkady, Hazem. And the article was included in Bioorganic Chemistry in 2021.Computed Properties of C8H4Cl2N2 This article mentions the following:

New series of [1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one I [R = Et, Ph, 3-ClC₆H₄, etc.; X = CH₂] and [1,2,4]triazolo[4,3-a]quinoxaline derivatives I [X = SCH₂] were designed, synthesized, and biol. assessed for their anti-proliferative activities against two selected tumor cell lines MCF-7 and HepG2. Comparing to sorafenib (IC₅₀ = 2.17 ± 0.13 and 3.51 ± 0.21μM against MCF-7 and HepG2, resp.), compounds I [R = 4-ClC₆H₄, 2,5-di-ClC₆H₃, 2-HO-5-MeC₆H₃; X = CH₂, SCH₂] exhibited the highest activities against the examined cell lines with IC₅₀ values extending from 4.1 ± 0.4 to 11.7 ± 1.1μM. Furthermore, VEGFR-2 inhibitory activities were assessed for all the synthesized compounds as potential mechanisms for their anti-proliferative activities. Compounds I [R = 4-ClC₆H₄, 2,5-di-ClC₆H₃, 2-HO-5-MeC₆H₃; X = CH₂, SCH₂] displayed prominent inhibitory efficiency vs. VEGFR-2 kinase with IC₅₀ value ranging from 3.4 ± 0.3 to 6.8 ± 0.5 nM. Fascinatingly, the results of VEGFR-2 inhibitory assays were matched with that of the cytotoxicity data, where the most potent anti-proliferative derivatives exhibited promising VEGFR-2 inhibitory activities. Further studies displayed the ability of compound I [R = 4-ClC₆H₄; X = CH₂] to induce apoptosis in HepG2 cells and can arrest the growth of such cells at the G2/M phase. Also, compound I [R = 4-ClC₆H₄; X = CH₂] produced a significant increase in the level of BAX/Bcl-2 ratio (3.8-fold), caspase- 3 (1.8-fold), and caspase-9 (1.9-fold) compared to the control cells. Mol. docking studies were carried out to investigate the possible binding interaction inside the active site of the VEGFR-2. In the experiment, the researchers used many compounds, for example, 2,3-Dichloroquinoxaline (cas: 2213-63-0Computed Properties of C8H4Cl2N2).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4?-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5- carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and the structures are stable.

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Diethoxyphosphorylthioacetamide in the reaction with 2,3- dichloroquinoxaline acted as a thionating reagent, giving diethoxyphosphorylacetonitrile and 2-chloro-3-[(3-chloro-2-quinoxalinyl)thio] quinoxaline. Reactions of phosphorylthioacetamides with N-methylquinoxalinium iodide in alcohol media in the presence of a base proceeded stereoselectively to afford cis-3-phosphoryl-1,3,3a,4,9,9a-hexahydro-2H-pyrrolo[2,3-b]quinoxaline-2- thiones.

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A dual-coded dynamic material was created by the bimodal self-assembly protocol sketched in the scheme. The combination of two orthogonal and reversible interactions, namely solvophobic aggregation (SA) and metal coordination (MC), allows precise control at each step of the self-assembly cycle, leading to the formation of rodlike supramolecular architectures. Eight illustrious organic chemists in one pot! A route from protected monosaccharides to novel C-glycosides and Clinked disaccharides is described which involves tandem Horner-WadsworthEmmons/conjugate addition (Michaeltype), followed by tandem halogenation/Ramberg-Baecklund reaction using the Meyers-Chan procedure (see scheme, R = protected saccharide). The calculated structures of a supported Rh6 cluster (depicted) demonstrate that protons of surface OH groups of the oxide support migrate onto the cluster. This migration results in the oxidation of metal atoms that are in close contact with the support. The energy released by this reverse hydrogen spillover is estimated to be 120 kmol-1 per OH group. A more sensitive approach: A variation on the heteronuclear multiple-bond correlation technique has been devised which can determine the conformation around the glycosidic bonds in oligosaccharides and glycopeptides. The key section of the studied glycopeptide 1 is shown, for which measurements of the torsion angles phi and psi derived from 3J(C,H) coupling constants and cross-correlated relaxation rates, compare favorably with those determined by X-ray diffraction or molecular dynamic analysis. Highly unsaturated gamma-lactones are formed in good to high yields from 2-(propargyl)allyl phosphates and carbon monoxide in the presence of a palladium catalyst (see scheme). The reaction proceeds efficiently under mild reaction conditions (at 80C under an ambient pressure of CO). A change in shift! In contrast to the red shift commonly found in organic polyynes and other metal-alkynyl systems, a blue shift in the transition energy was observed in electronic absorption and emission studies on a novel series of structurally characterized dinuclear platinum(II)terpyridyl complexes [{Pt(tBu3-tpy)}2- (CC)n](X)2 (1-3; tBu3-tpy=4,4?,4?-tritert-butyl-2,2?: 6?,2?-terpyridine) upon increasing the extent of pi conjugation of the alkynyl bridge.

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As a continuation of our search for new heterocyclic compounds, the synthesis of pyrimido[5?,4?:5,6][1,4]thiazino[2,3-b]quinoxaline ring system is described. A series of new derivatives of this heterocyclic system (3a?d) have been synthesized through the one-pot heterocyclization of the appropriate 5-amino6-methylpyrimidine-4-thiols and 2,3-dichloroquinoxaline in the presence of K2CO3 in dimethylformamide under reflux. N-alkylation of the synthesized compounds with alkyl halides in KOH/dimethylformamide also gave the desired new derivatives of N-alkylated pyrimido[5?,4?:5,6][1,4]thiazino[2,3-b]quinoxalines (4a?h). All the synthesized products were characterized and confirmed by their spectroscopic and microanalytical data.

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Treatment of N,N’-di(quinoxalin-2-yl)diazene N-oxide 3 with strong acids did not give the expected Wallach-type hydroxylated product, but the first representative of the pentacyclic imidazo[1,2-a:4,5-b’]diquinoxaline system 5. Heating in a weaker acid or neat furnished 1-(quinoxalin-2-yl)quinoxalin-2(1H)- one 12. The structures of these products were confirmed by independent synthesis and NMR experiments or X-ray crystallography. ARKAT USA, Inc.

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The link between PDE4 and apoptosis prompted us to design and synthesize for the first time a series of novel 1-thienyl pyrroloquinoxalines as potential PDE4 inhibitors/apoptotic agents. A ligand-free Pd-catalyzed C-N cross-coupling/cyclization strategy has been developed for the rapid and milder access to this class of compounds some of which showed interesting pharmacological properties when tested in vitro and in zebrafish embryos.

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Quinoxaline – Wikipedia,
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