Day: February 7, 2023

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

Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands was written by Ingoglia, Bryan T.;Buchwald, Stephen L.. And the article was included in Organic Letters in 2017.Category: quinoxaline This article mentions the following:

Palladium-based oxidative addition complexes derived from aryl triflates or bromides and the bulky phosphine ligands AlPhos and t-BuBrettPhos were prepared as easily prepared, air-stable, and effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The structure of an AlPhos (trifluoromethylphenyl)palladium triflate complex benzene solvate was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Category: quinoxaline).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed N-Arylation of Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl (Pseudo)halides at Room Temperature was written by Tassone, Joseph P.;MacQueen, Preston M.;Lavoie, Christopher M.;Ferguson, Michael J.;McDonald, Robert;Stradiotto, Mark. And the article was included in ACS Catalysis in 2017.Reference of 5448-43-1 This article mentions the following:

Whereas the metal-catalyzed C(sp2)-N cross-coupling of cyclopropylamine with aryl electrophiles represents an attractive route to pharmaceutically relevant N-arylcyclopropylamines, few catalysts that are capable of effecting such transformations have been identified. Herein, the nickel-catalyzed C(sp2)-N cross-coupling of cyclopropylamine and related nucleophiles, including ammonium salts, with (hetero)aryl (pseudo)halides is reported for the first time, with the demonstrated scope of reactivity exceeding that displayed by all previously reported catalysts (Pd, Cu, or other). Our preliminary efforts to effect the N-arylation of cyclopropylamine with (hetero)aryl chlorides at room temperature by use of (L)NiCl(o-tolyl) pre-catalysts (L = PAd-DalPhos, C1; L = JosiPhos CyPF-Cy, C2) were unsuccessful, despite the established efficacy of C1 and C2 in transformations of other primary alkylamines. However, systematic modification of the ancillary ligand (L) structure enabled success in such transformations, with new and crystallog. characterized (L)NiCl(o-tolyl) pre-catalysts incorporating o-phenylene-bridged bisphosphines featuring either phosphatrioxaadamantane and PCy2 (L = L3, CyPAd-DalPhos; C3), P(o-tolyl)2 and P(t-Bu)2 (L = L4; C4), or PCy2 and P(t-Bu)2 (L = L5; C5) donor pairings proving to be particularly effective. In employing the air-stable pre-catalyst C3 in cross-couplings of cyclopropylamine, substituted electrophiles encompassing an unprecedentedly broad range of heteroaryl (pyridine, isoquinoline, quinoline, quinoxaline, pyrimidine, purine, benzothiophene, and benzothiazole) and (pseudo)halide (chloride, bromide, mesylate, tosylate, triflate, sulfamate, and carbamate) structures were employed successfully, in the majority of cases under mild conditions (3 mol% Ni, 25°). Preliminary studies also confirmed the ability of C3 to effect the N-arylation of cyclopropanemethylamine hydrochloride and cyclobutylamine hydrochloride under similar conditions. A notable exception in this chem. was observed specifically in the case of electron-rich aryl chlorides, where the use of C4 in place of C3 proved more effective. In keeping with this observation, catalyst inhibition by 4-chloroanisole was observed in the otherwise efficient cross-coupling of cyclopropylamine and 3-chloropyridine when using C3. Competition studies involving C3 revealed a (pseudo)halide reactivity preference (Cl > Br, OTs). 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. 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 antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Reference of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider