Heterocyclic Building Blocks-quinoxaline

From simple quinoxalines to potent oxazolo[5,4-f]quinoxaline inhibitors of glycogen-synthase kinase 3 (GSK3) was written by Lassagne, Frederic;Dugueperoux, Camille;Roca, Carlos;Perez, Concepcion;Martinez, Ana;Baratte, Blandine;Robert, Thomas;Ruchaud, Sandrine;Bach, Stephane;Erb, William;Roisnel, Thierry;Mongin, Florence. And the article was included in Organic & Biomolecular Chemistry in 2020.HPLC of Formula: 166402-16-0 This article mentions the following:

2,7-Disubstituted oxazolo[5,4-f]quinoxalines were synthesized from 6-amino-2-chloroquinoxaline in four steps (iodination at C5, substitution of the chloro group, amidation and copper-catalyzed cyclization) affording 28 to 44% overall yields. 2,8-Disubstituted oxazolo[5,4-f]quinoxaline was similarly obtained from 6-amino-3-chloroquinoxaline (39% overall yield). For the synthesis of other oxazolo[5,4-f]quinoxalines, amidation was rather performed before substitution; moreover, time-consuming purification steps were avoided between the amines and the final products (38 to 54% overall yields). Finally, a more efficient method involving merging of the last two steps in a sequential process was developed to access more derivatives (37 to 65% overall yields). Most of the oxazolo[5,4-f]quinoxalines were evaluated for their activity on a panel of protein kinases, and a few 2,8-disubstituted derivatives proved to inhibit GSK3 kinase. While experiments showed an ATP-competitive inhibition on GSK3β, structure-activity relationships allowed us to identify 2-(3-pyridyl)-8-(thiomorpholino)oxazolo[5,4-f]quinoxaline as the most potent inhibitor with an IC₅₀ value of about 5 nM on GSK3α. In the experiment, the researchers used many compounds, for example, 3-Chloroquinoxalin-6-amine (cas: 166402-16-0HPLC of Formula: 166402-16-0).

3-Chloroquinoxalin-6-amine (cas: 166402-16-0) 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. 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.HPLC of Formula: 166402-16-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models was written by Le Douaron, Gael;Ferrie, Laurent;Sepulveda-Diaz, Julia E.;Amar, Majid;Harfouche, Abha;Seon-Meniel, Blandine;Raisman-Vozari, Rita;Michel, Patrick P.;Figadere, Bruno. And the article was included in Journal of Medicinal Chemistry in 2016.Name: 3-Chloroquinoxalin-6-amine This article mentions the following:

Parkinson’s disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, the authors have designed and synthesized a 2nd-generation of quinoxaline-derived mols. based on structure-activity relation studies, which led previously to the discovery of the authors’ 1st neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of the authors’ newly synthesized quinoxaline-derived compounds led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder. In the experiment, the researchers used many compounds, for example, 3-Chloroquinoxalin-6-amine (cas: 166402-16-0Name: 3-Chloroquinoxalin-6-amine).

3-Chloroquinoxalin-6-amine (cas: 166402-16-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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: 3-Chloroquinoxalin-6-amine

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Antidepressant potential of 5-HT₃ receptor antagonist, N-n- propyl-3-ethoxyquinoxaline-2-carboxamide (6n) was written by Mahesh, R.;Bhatt, S.;Devadoss, T.;Jindal, A. K.;Gautam, B. K.;Pandey, D. K.. And the article was included in Journal of Young Pharmacists in 2012.Related Products of 49679-45-0 This article mentions the following:

The present study was designed to evaluate the antidepressant potential of 5-HT3 receptor antagonist N-n-propyl-3-ethoxyquinoxaline-2-carboxamide (6n). The compound “6n” with optimum log P and pA₂ value identified from a series of compounds synthesized in our laboratory was subjected to forced Swim Test (FST) (1, 2, and 4 mg/kg, i.p) and Tail Suspension Test (TST) (1, 2, and 4 mg/kg, i.p.). The compound “6n” significantly reduced the duration of immobility in mice without affecting the baseline locomotion. Moreover, “6n” (2 mg/kg, i.p.) potentiated the 5-hydroxytryptophan (5-HTP)-induced head twitch responses in mice and “6n” at tested dose (1 and 2 mg/kg, i.p.) reversed the reserpine-induced hypothermia in rats. In interaction studies of “6n” with various standard drugs/ligands using FST, “6n” (1 mg/kg, i.p.) potentiated the antidepressant effect of venlafaxine (4 and 8 mg/kg, i.p.) and fluoxetine (10 and 20 mg/kg, i.p.). Addnl., “6n” (1 and 2 mg/kg, i.p.) influenced the effect of harmane (5 mg/kg, i.p.) as well as reversed the effect of parthenolide (1 mg/kg, i.p.) by reducing the duration of immobility in FST. Furthermore, “6n” (1 mg/kg/, i.p.) potentiated the effect of bupropion (10 and 20 mg/kg, i.p.) in TST. Chronic “6n” (1 and 2 mg/kg, i.p.) treatment attenuated the behavioral abnormalities in olfactory bulbectomized rats. In conclusion, these various findings reiterated the antidepressant-like effects of “6n” in behavioral models of depression. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Related Products of 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.Related Products of 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Study of heterocyclic quinones. XXVII. Catalysis by copper ions of the reaction of quinoxaline-5,8-quinones with amines was written by Chernyak, S. A.;Tsizin, Yu. S.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1976.Product Details of 6639-82-3 This article mentions the following:

Aminomethoxyquinoxaline I, prepared in 71% yield from nitroaminoanisole and N2H4.H2O by cyclization, nitration, and reduction, was oxidized by ·ON(SO3K)2 to give 65% II (R1 = OMe, R2 = H) which was aminated by morpholine and piperidine to give 86 and 78% II (R1 = morpholino, piperidino, R2 = H), resp. Addnl. obtained were 65-83% II (R1 = R2 = morpholino, piperidino; R1 = piperidino, R2 = morpholino) and 95% CuCl2 complex of II (R1 = piperidino, R2 = H). In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Product Details of 6639-82-3).

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. 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.Product Details of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Position-dependent effects of internal heavy atoms on highly resolved electronic spectra and luminescence properties of some quinoxalines substituted at the homocyclic ring was written by Lewanowicz, A.;Lipinski, J.;Ruziewicz, Z.;Szymczak, A.;Szynkarczuk, J.. And the article was included in Journal of Luminescence in 1989.Related Products of 5448-43-1 This article mentions the following:

Highly resolved phosphorescence and S₁(n,π^*)  S₀ phosphorescence excitation spectra and some photophys. properties of monohaloquinoxalines (I; R = H, R¹ = Br, Cl; R = Br, Cl, R¹ = H) are compared. Exptl. data are supplemented by theor. study of the electronic structures, performed with the use of a modified INDO CI method. Insensitivity of phosphorescence lifetimes of I to the nature of the solvent is discussed. The substituent position-dependent T₁ state energy is recognized as the main factor differentiating the vibronic structure of the phosphorescence spectra and the luminescence properties of I. 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. 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.Related Products of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

PhPAd-DalPhos: Ligand-Enabled, Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles with Bulky Primary Alkylamines was written by Tassone, Joseph P.;England, Emma V.;MacQueen, Preston M.;Ferguson, Michael J.;Stradiotto, Mark. And the article was included in Angewandte Chemie, International Edition in 2019.Related Products of 5448-43-1 This article mentions the following:

The base metal-catalyzed C-N cross-coupling of bulky α,α,α-trisubstituted primary alkylamines with (hetero)aryl electrophiles represents a challenging and under-developed class of transformations that is of significant potential utility, including in the synthesis of lipophilic active pharmaceutical ingredients. Herein, the authors report that a new, air-stable Ni(II) pre-catalyst incorporating the optimized ancillary ligand PhPAd-DalPhos enables such transformations of (hetero)aryl chloride, bromide, and tosylate electrophiles to be carried out for the first time with substrate scope rivaling that achieved using state-of-the-art Pd catalysts, including room temperature cross-couplings of (hetero)aryl chlorides that are unprecedented for any catalyst (Pd, Ni, or other). 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. 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. 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.Related Products of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quinoxaline chemistry. Part XVII. Methyl [4-(substituted 2-quinoxalinyloxy) phenyl] acetates and ethyl N-{[4-(substituted 2-quinoxalinyloxy) phenyl] acetyl} glutamates analogs of methotrexate: synthesis and evaluation of in vitro anticancer activity was written by Piras, Sandra;Loriga, Mario;Paglietti, Giuseppe. And the article was included in Farmaco in 2004.Synthetic Route of C11H9ClN2O2 This article mentions the following:

Fourteen out of 21 quinoxaline derivatives described in the present paper were selected at NCI for evaluation of their in vitro anticancer activity. Preliminary screening showed that some derivatives exhibited a moderate to strong growth inhibition activity on various tumor panel cell lines between 10^-5 and 10^-4 M concentrations Interesting selectivities were also recorded between 10^-8 and 10^-6 M for the compounds 9 and 13. 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. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. 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.Synthetic Route of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-catalyzed electrochemical Minisci acylation of aromatic N-heterocycles with α-keto acids via ligand-to-metal electron transfer pathway was written by Ding, Hang;Xu, Kun;Zeng, Cheng-Chu. And the article was included in Journal of Catalysis in 2020.Safety of 6-Chloroquinoxaline This article mentions the following:

A nickel-catalyzed electrochem. methodol. for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids had been developed. The reaction was performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric anal. disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Safety of 6-Chloroquinoxaline).

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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a ruthenium-catalyzed hydrogen transfer strategy was written by Xie, Feng;Zhang, Min;Jiang, Huanfeng;Chen, Mengmeng;Lv, Wan;Zheng, Aibin;Jian, Xiujuan. And the article was included in Green Chemistry in 2015.Related Products of 5448-43-1 This article mentions the following:

Via a ruthenium-catalyzed hydrogen transfer strategy, we have demonstrated a one-pot method for efficient synthesis of quinoxalines e. g., I, from 2-nitroanilines and biomass-derived vicinal diols for the first time. In such a synthetic protocol, the diols and the nitro group serve as the hydrogen suppliers and acceptors, resp. Hence, there is no need for the use of external reducing agents. Moreover, it has the advantages of operational simplicity, broad substrate scope and the use of renewable reactants, offering an important basis for accessing various quinoxaline derivatives 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. Quinoxalines are used in the treatment of bacterial, cancer, and HIV infections. Moreover, varenicline, a clinical drug is used for treating nicotine addiction, also contains quinoxaline moiety.Related Products of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by NH₄I was written by Wang, Qing-Qing;Xu, Kun;Jiang, Yang-Ye;Liu, Yong-Guo;Sun, Bao-Guo;Zeng, Cheng-Chu. And the article was included in Organic Letters in 2017.Application In Synthesis of 6-Methoxyquinoxaline This article mentions the following:

Electron-deficient aromatic nitrogen heterocycles, particularly pyrazines and quinoxalines, underwent chemoselective and green electrochem. Minisci acylations with α-ketoacids such as pyruvic acid mediated by NH₄I, LiClO₄, and hexafluoroisopropanol in MeCN to give heteroaryl ketones such as 2-acetylquinoxaline in 18-65% yields. Cyclic voltammetry and control experiments were used to delineate the mechanism of the Minisci acylation; I₂ formed in situ likely reacts with carboxylate anions to yield acyl hypoiodites which then undergo decarboxylation to acyl radicals. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Application In Synthesis of 6-Methoxyquinoxaline).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. 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.Application In Synthesis of 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider