Category: quinoxaline

The infrared spectra of polycyclic heteroaromatic compounds. III. 2-, 5-, and 6-substituted quinoxalines was written by Cheeseman, G. W. H.;Katritzky, A. R.;Ridgewell, B. J.. And the article was included in Journal of the Chemical Society in 1963.Formula: C8H5ClN2 This article mentions the following:

The infrared spectra of quinoxaline, 9 of its 2-substituted, 5 of its 5-substituted, and 8 of its 6-substituted derivatives are recorded and discussed, with tentative assignments of characteristic bands to specific mol. vibration modes. Cf. CA 56, 1073g. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Formula: C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines have received a significant amount of attention due to their potential use in fighting various pathophysiological conditions like epilepsy, Parkinson’s, and Alzheimer’s diseases. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

3-Arylamino-quinoxaline-2-carboxamides inhibit the PI3K/Akt/mTOR signaling pathways to activate P53 and induce apoptosis was written by Chen, Nan-Ying;Lu, Ke;Yuan, Jing-Mei;Li, Xiao-Juan;Gu, Zi-Yu;Pan, Cheng-Xue;Mo, Dong-Liang;Su, Gui-Fa. And the article was included in Bioorganic Chemistry in 2021.Synthetic Route of C11H9ClN2O2 This article mentions the following:

Thirty-eight new 3-arylaminoquinoxaline-2-carboxamide derivatives were in silico designed, synthesized and their cytotoxicity against five human cancer cell lines and one normal cells WI-38 were evaluated. Mol. mechanism studies indicated that N-(3-Aminopropyl)-3-(4-chlorophenyl) amino-quinoxaline-2-carboxamide (6be), the compound with the most potent anti-proliferation can inhibit the PI3K-Akt-mTOR pathway via down regulating the levels of PI3K, Akt, p-Akt, p-mTOR and simultaneously inhibit the phosphorylation of Thr308 and Ser473 residues in Akt kinase to servers as a dual inhibitor. Further investigation revealed that 6be activate the P53 signal pathway, modulated the downstream target gene of Akt kinase such p21, p27, Bax and Bcl-2, caused the fluctuation of intracellular ROS, Ca2+ and mitochondrial membrane potential to induce cell cycle arrest and apoptosis in MGC-803 cells. 6be also display moderate anti-tumor activity in vivo while displaying no obvious adverse signs during the drug administration. The results suggest that 3-arylaminoquinoxaline-2-carboxamide derivatives might server as new scaffold for development of PI3K-Akt-mTOR inhibitor. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Synthetic Route of C11H9ClN2O2).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. 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.Synthetic Route of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The infrared spectra of polycyclic heteroaromatic compounds. III. 2-, 5-, and 6-substituted quinoxalines was written by Cheeseman, G. W. H.;Katritzky, A. R.;Ridgewell, B. J.. And the article was included in Journal of the Chemical Society in 1963.Name: 6-Methoxyquinoxaline This article mentions the following:

The infrared spectra of quinoxaline, 9 of its 2-substituted, 5 of its 5-substituted, and 8 of its 6-substituted derivatives are recorded and discussed, with tentative assignments of characteristic bands to specific mol. vibration modes. Cf. CA 56, 1073g. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Name: 6-Methoxyquinoxaline).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. 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.Name: 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions was written by Bains, Amreen K.;Singh, Vikramjeet;Adhikari, Debashis. And the article was included in Journal of Organic Chemistry in 2020.Related Products of 5448-43-1 This article mentions the following:

Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora of heterocyclic rings. Herein, we report an efficacious, nickel-catalyzed synthesis of two important heterocycles such as quinoline and quinoxaline. The catalyst is molecularly defined, is phosphine-free, and can operate at a mild reaction temperature of 80°C. Both the heterocycles can be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alc./1-phenylethanol and diamine/diol, resp., in a shorter span of reaction time. This environmentally benign synthetic protocol employing an inexpensive catalyst can rival many other transition-metal systems that have been developed for the fabrication of two putative heterocycles. Mechanistically, the dehydrogenation of secondary alc. follows clean pseudo-first-order kinetics and exhibits a sizable kinetic isotope effect. Intriguingly, this catalyst provides an example of storing the trapped hydrogen in the ligand backbone, avoiding metal-hydride formation. Easy regeneration of the oxidized form of the catalyst under aerobic/O₂ oxidation makes this protocol eco-friendly and easy to handle. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Related Products of 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Related Products of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Binding Mode of an α-Amino Acid-Linked Quinoxaline-2,3-dione Analogue at Glutamate Receptor Subtype GluK1 was written by Demmer, Charles S.;Moeller, Charlotte;Brown, Patricia M. G. E.;Han, Liwei;Pickering, Darryl S.;Nielsen, Birgitte;Bowie, Derek;Frydenvang, Karla;Kastrup, Jette S.;Bunch, Lennart. And the article was included in ACS Chemical Neuroscience in 2015.Application In Synthesis of 6-Bromoquinoxaline-2,3(1H,4H)-dione This article mentions the following:

Two α-amino acid-functionalized quinoxalines, 1a (CNG-10301) and 1b (CNG-10300), of a quinoxaline moiety coupled to an amino acid moiety were designed, synthesized, and characterized pharmacol. While 1a displayed low affinity at native AMPA, KA, and NMDA receptors, and at homomeric GluK1,3 receptors, the affinity for GluK2 was in the midmicromolar range (K_i = 136 μM), 1b displayed low to midmicromolar range binding affinity at all the iGluRs (K_i = 9-126 μM). In functional experiments (outside-out patches excised from transfected HEK293T cells), 100 μM 1a partially blocked GluK1 (33% peak response), while GluK2 was unaffected (96% peak response). Furthermore, 1a was shown not to be an agonist at GluK1 and GluK2 at 100 μM. On the other hand, 100 μM 1b fully antagonized GluK1 (8% peak response) but only partially blocked GluK2 (33% peak response). An X-ray structure at 2.3 Å resolution of 1b in the GluK1-LBD (ligand-binding domain) disclosed an unexpected binding mode compared to the predictions made during the design phase; the quinoxaline moiety remains to act as an amino acid bioisostere, but the amino acid moiety is oriented into a new area within the GluK1 receptor. The structure of the GluK1-LBD with 1b showed a large variation in domain openings of the three mols. from 25° to 49°, demonstrating that the GluK1-LBD is capable of undergoing major domain movements. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Application In Synthesis of 6-Bromoquinoxaline-2,3(1H,4H)-dione).

6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. Quinoxalines are used as dyes, pharmaceuticals, and antibiotics such as echinomycin, levomycin exhibiting antitumoral properties. Quinoxalines establish also the basis of anthelmintics and receptor antagonists.Application In Synthesis of 6-Bromoquinoxaline-2,3(1H,4H)-dione

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ³-Iodinane Compounds was written by Troian-Gautier, Ludovic;De Winter, Julien;Gerbaux, Pascal;Moucheron, Cecile. And the article was included in Journal of Organic Chemistry in 2013.Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione This article mentions the following:

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chem. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione).

6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) 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.Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Design and synthesis of a novel mitochondria-targeted osteosarcoma theranostic agent based on a PIM1 kinase inhibitor was written by Yi, Xinzeyu;Cao, Zhi;Yuan, Ying;Li, Wen;Cui, Xinyue;Chen, Zilin;Hu, Xiang;Yu, Aixi. And the article was included in Journal of Controlled Release in 2021.Formula: C11H9ClN2O2 This article mentions the following:

Osteosarcoma (OS) is the most common malignancy of the skeletal system, with a poor prognosis and high rate of recurrence. Adequate surgical margin and adjuvant chemotherapy improve the overall survival and limb salvage rate of osteosarcoma patients. Previous studies have showed that OS exhibits an increase in the expression of proviral integration site for Moloney murine leukemia virus 1 (PIM1) kinase, and high levels of PIM1 are also associated with poor OS prognosis and metastasis. We exploited the overexpression of proto-oncogenic PIM1 in OS toward the development of a novel near-IR imaging and targeted therapeutic agent, namely QCAi-Cy7d by conjugating a PIM1 small mol. inhibitor and heptamethine cyanine dye, for simultaneous guiding surgery and chemotherapy. QCAi-Cy7d showed targeted imaging and anticancer activities against OS in vitro and vivo without any obvious toxicity, and its antitumoral activity was much greater than the parent PIMI inhibitor. These results demonstrated the potential of new conjugate of PIM1 inhibitor and near-IR imaging, supporting structure-based design and development of theranostic agents for precise tumor imaging and targeted treatment. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Formula: C11H9ClN2O2).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Compounds possessing quinoxaline derivatives were bestowed with a variety of significant biological properties such as antiviral, antimalarial, anticancer, DNA intercalation, DNA duplex stabilization, and many others. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed Amination of Aryl Chlorides with Ammonia or Ammonium Salts was written by Green, Rebecca A.;Hartwig, John F.. And the article was included in Angewandte Chemie, International Edition in 2015.Reference of 5448-43-1 This article mentions the following:

The nickel-catalyzed amination of aryl chlorides to form primary arylamines with ammonia or ammonium sulfate and a well-defined single-component nickel(0) pre-catalyst, containing a Josiphos ligand and an η²-bound benzonitrile ligand, was reported. This system also catalyzed the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Reference of 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) 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.Reference of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source was written by Kariofillis, Stavros K.;Shields, Benjamin J.;Tekle-Smith, Makeda A.;Zacuto, Michael J.;Doyle, Abigail G.. And the article was included in Journal of the American Chemical Society in 2020.Name: 6-Chloroquinoxaline This article mentions the following:

A radical approach for the methylation of (hetero)aryl chlorides R-Cl (R = 4-CNC₆H₄, 2-CF₃C₆H₄, 9-oxo-thioxanthen-2-yl, 4-(6-methylpyridin-2-yl)phenyl, 4-phenythiazol-2-yl, etc.) using nickel/photoredox catalysis wherein tri-Me orthoformate, a common laboratory solvent, serves as a Me source has been described. This method permits methylation of (hetero)aryl chlorides and acyl chlorides R¹C(O)Cl (R¹ = (CH₂)₁₀-CH₃, adamantan-1-yl, C₆H₅O, N,N-diphenylamino, etc.) at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that tri-Me orthoformate serves as a source of Me radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Name: 6-Chloroquinoxaline).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines have received a significant amount of attention due to their potential use in fighting various pathophysiological conditions like epilepsy, Parkinson’s, and Alzheimer’s diseases. 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.Name: 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Development and Synthesis of DNA-Encoded Benzimidazole Library was written by Ding, Yun;Chai, Jing;Centrella, Paolo A.;Gondo, Chenaimwoyo;De Lorey, Jennifer L.;Clark, Matthew A.. And the article was included in ACS Combinatorial Science in 2018.Quality Control of Quinoxaline-5-carbaldehyde This article mentions the following:

Encoded library technol. (ELT) is an effective approach to the discovery of novel small-mol. ligands for biol. targets. A key factor for the success of the technol. is the chem. diversity of the libraries. Here we report the development of DNA-conjugated benzimidazoles. Using 4-fluoro-3-nitrobenzoic acid as a key synthon, we synthesized a 320 million-member DNA-encoded benzimidazole library using Fmoc-protected amino acids, amines and aldehydes as diversity elements. Affinity selection of the library led to the discovery of a novel, potent and specific antagonist of the NK3 receptor. In the experiment, the researchers used many compounds, for example, Quinoxaline-5-carbaldehyde (cas: 141234-08-4Quality Control of Quinoxaline-5-carbaldehyde).

Quinoxaline-5-carbaldehyde (cas: 141234-08-4) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Quality Control of Quinoxaline-5-carbaldehyde

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider