Month: January 2023

Graphene oxide (GO) or reduced graphene oxide (rGO): efficient catalysts for one-pot metal-free synthesis of quinoxalines from 2-nitroaniline was written by Roy, Babli;Ghosh, Sujit;Ghosh, Pranab;Basu, Basudeb. And the article was included in Tetrahedron Letters in 2015.Related Products of 6639-82-3 This article mentions the following:

A straightforward one-pot preparation of library of quinoxalines from 2-nitroanilines under entirely metal-free conditions is described. Initial reduction of nitroaniline with hydrazine hydrate is efficiently catalyzed by graphene oxide (GO) or reduced graphene oxide (rGO), and further one-pot tandem reactions with 1,2-dicarbonyl compounds or with α-hydroxy ketones afford quinoxalines in excellent yields. The catalyst is recovered, characterized, and is recyclable for consecutive four runs examined with appreciable conversions. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Related Products 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. 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.Related Products of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis, Biological Evaluation, and In Silico Studies of New Acetylcholinesterase Inhibitors Based on Quinoxaline Scaffold was written by Suwanhom, Paptawan;Saetang, Jirakrit;Khongkow, Pasarat;Nualnoi, Teerapat;Tipmanee, Varomyalin;Lomlim, Luelak. And the article was included in Molecules in 2021.Recommanded Product: 5448-43-1 This article mentions the following:

A quinoxaline scaffold exhibits various bioactivities in pharmacotherapeutic interests. In this research, twelve quinoxaline derivatives were synthesized and evaluated as new acetylcholinesterase inhibitors. Authors found all compounds showed potent inhibitory activity against acetylcholinesterase (AChE) with IC₅₀ values of 0.077 to 50.080μM, along with promising predicted drug-likeness and blood-brain barrier (BBB) permeation. In addition, potent butyrylcholinesterase (BChE) inhibitory activity with IC₅₀ values of 14.91 to 60.95μM was observed in some compounds Enzyme kinetic study revealed the most potent compound I as a mixed-type AChE inhibitor. No cytotoxicity from the quinoxaline derivatives was noticed in the human neuroblastoma cell line (SHSY5Y). In silico study suggested the compounds preferred the peripheral anionic site (PAS) to the catalytic anionic site (CAS), which was different from AChE inhibitors (tacrine and galanthamine). Author had proposed the mol. design guided for quinoxaline derivatives targeting the PAS site. Therefore, the quinoxaline derivatives could offer the lead for the newly developed candidate as potential acetylcholinesterase inhibitors. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Recommanded Product: 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. 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.Recommanded Product: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis and reactions of 1H-1,5-benzodiazepino[2,3-b]quinoxaline, a new heterocyclic system was written by Pillai, P. Madhavan;Bhat, V. Sanjeev. And the article was included in Synthetic Communications in 1991.Application of 49679-45-0 This article mentions the following:

Title compounds I (R = H, OH, Cl, OMe, OEt, OCHMe₂, NR¹₂; R¹ = H, Et; NR¹₂ = morpholino, piperidino, 1-pyrrolidinyl) were prepared by elaboration of I (R = OH) which was prepared in high yields by the cyclocondensation of o-C₆H₄(NH₂)₂ with quinoxalinecarboxylates II (R² = Cl, OH). In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Application of 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) 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. 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 of 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Examining the Impact of Heteroaryl Variants of PAd-DalPhos on Nickel-Catalyzed C(sp²)-N Cross-Couplings was written by Clark, Jillian S. K.;McGuire, Ryan T.;Lavoie, Christopher M.;Ferguson, Michael J.;Stradiotto, Mark. And the article was included in Organometallics in 2019.Recommanded Product: 5448-43-1 This article mentions the following:

We report herein on the synthesis of new heteroaryl analogs of PAd-DalPhos and related bis(di(o-tolyl)phosphino) ancillary ligand variants based on pyridine or thiophene backbone structures, and their application in nickel-catalyzed C(sp²)-N cross-couplings under challenging reaction conditions. The 3,4-disubstituted thiophene-based ancillary ligand ThioPAd-DalPhos (L8) was observed to be particularly effective in the nickel-catalyzed C(sp²)-N cross-coupling of primary alkylamines, and the derived precatalyst (L8)NiCl(o-tolyl) (C2) was found to offer improved performance vs. the related PAd-DalPhos-derived precatalyst C1 in such transformations. In using C2, cross-couplings of various primary alkylamines and (hetero)aryl-X electrophiles (X = Cl, Br, OTs) proceeded under unprecedentedly mild reaction conditions (0.25-0.50 mol % Ni), including examples conducted at room temperature Also reported herein are the results of our combined exptl./DFT computational study directed toward gaining insight regarding the improved catalytic performance of C2 vs. C1. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Recommanded Product: 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. 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.Recommanded Product: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quinoxaline chemistry. Part 4. 2-(R)-Anilinoquinoxalines as nonclassical antifolate agents. Synthesis, structure elucidation and evaluation of in vitro anticancer activity was written by Loriga, Mario;Fiore, Maria;Sanna, Paolo;Paglietti, Giuseppe. And the article was included in Farmaco in 1995.Quality Control of 3-Chloroquinoxalin-6-amine This article mentions the following:

Thirty-five quinoxalines bearing a substituted aniline group on position 2 and various substituents on positions 3,6,7 and 8 were prepared in order to evaluate in vitro anticancer activity. Structural elucidation of some isomeric quinoxalinones formed by ring closure of 4-substituted-1,2-diaminobenzenes with dicarbonyl compounds was achieved by comparison with one isomer coming from an unambiguous independent route. Preliminary in vitro screening at NCI showed that many compounds exhibited a moderate to strong growth inhibition activity on various cells lines between 10^-5 and 10^-4 molar concentrations In the experiment, the researchers used many compounds, for example, 3-Chloroquinoxalin-6-amine (cas: 166402-16-0Quality Control of 3-Chloroquinoxalin-6-amine).

3-Chloroquinoxalin-6-amine (cas: 166402-16-0) 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. 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.Quality Control of 3-Chloroquinoxalin-6-amine

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Diverse 2-Carboxamide-3-amino-Substituted Quinoxalines: Synthesis and Reactivity Investigation for Library Generation was written by Kowalski, Jennifer A.;Leonard, Scott F.;Lee, George E. Jr.. And the article was included in Journal of Combinatorial Chemistry in 2006.Product Details of 49679-45-0 This article mentions the following:

The development of a robust synthetic route applicable to parallel synthesis of diverse 2-carboxamide-3-amino-substituted quinoxalines is reported. In addition to the scope and limitations of the methods developed, a purification strategy employing solid-phase extraction (SPE) and application of the methods to a small parallel array of compounds are discussed. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Product Details of 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) 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.Product Details of 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Anti-depressant like activity of N-n-butyl-3-methoxyquinoxaline-2-carboxamide (6o) a 5-HT₃ receptor antagonist was written by Bhatt, Shvetank;Mahesh, Radhakrishnan;Devadoss, Thangaraj;Jindal, Ankur. And the article was included in Indian Journal of Experimental Biology in 2013.Product Details of 49679-45-0 This article mentions the following:

The compound 60 (at 0.5, 1 and 2 mg/kg, i.p.) with optimum log P and pA₂ value, was subjected to forced swim test (FST) and tail suspension test (TST). The compound 60 significantly reduced the duration of immobility in mice without affecting the base line locomotion in actophotometer. Moreover, 6o (2 mg/kg, i.p.), potentiated the 5-hydroxytryptophan (5-HTP)-induced head twitch responses in mice and at 1 and 2 mg/kg, i.p. antagonized the reserpine-induced hypothermia (RIH) in rats. In interaction studies with various standard drugs/ligands using FST, 6o (1 and 2 mg/kg, i.p.) potentiated the anti-depressant effect fluoxetine (5 mg/kg, i.p.) and reversed the depressant effect of parthenolide (1 mg/kg, i.p.) by reducing the duration of immobility. Furthermore, 60 (1 and 2 mg/kg, i.p.) potentiated the effect of bupropion (10 mg/kg, i.p.) in TST. The behavioral anomalies of the olfactory bulbectomized (OBX) rats were augmented by chronic 60 (1 and 2 mg/kg) treatment as observed from the modified open field test (parameters: ambulation, rearing, fecal pellet). The results suggest that compound 60 exhibited anti-depressant like effect in rodent models of depression. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Product Details of 49679-45-0).

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. 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.Product Details of 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Application of Diazaphospholidine/Diazaphospholene-Based Bisphosphines in Room-Temperature Nickel-Catalyzed C(sp²)-N Cross-Couplings of Primary Alkylamines with (Hetero)aryl Chlorides and Bromides was written by Gatien, Alexandre V.;Lavoie, Christopher M.;Bennett, Raymond N.;Ferguson, Michael J.;McDonald, Robert;Johnson, Erin R.;Speed, Alexander W. H.;Stradiotto, Mark. And the article was included in ACS Catalysis in 2018.Electric Literature of C8H5ClN2 This article mentions the following:

We report herein on the synthesis and catalytic application of a family of o-phenylene-bridged bisphosphine ancillary ligands featuring a bulky N-heterocyclic phosphine (NHP) donor fragment paired with an adjacent PR₂ donor group (R = alkyl, aryl), whereby the incorporation of phosphorus into either a saturated or unsaturated heterocyclic ring serves as a means of modulating the donicity of the NHP fragment. Screening of these ancillary ligands in representative nickel-catalyzed C(sp²)-N cross-coupling test reactions allowed for the identification of one variant, featuring a saturated NHP structure and an adjacent diphenylphosphino donor group (i.e., NHP-DalPhos), as being particularly effective in reactions involving primary alkylamines. Notably, application of the derived precatalyst (NHP-DalPhos)NiCl(o-tolyl) (C1) enabled the typically challenging monoarylation of structurally diverse primary alkylamines with (hetero)aryl chlorides or bromides at room temperature Also described are the results of our comparative d. functional theory computational anal. of nickel-catalyzed primary alkylamine C(sp²)-N cross-couplings employing PAd-DalPhos or NHP-DalPhos. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Electric Literature of C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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.Electric Literature of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Silver-Catalyzed Three-Component Approach to Quinolines Starting from Anilines, Aldehydes, and Alcohols was written by Zhang, Xu;Liu, Wenmin;Sun, Ruixue;Xu, Xuefeng;Wang, Zhiqiang;Yan, Yanlei. And the article was included in Synlett in 2016.SDS of cas: 49679-45-0 This article mentions the following:

In the presence of AgOTf and triflic acid, anilines, aryl aldehydes and cyclohexanecarboxaldehyde, and alcs. (arylethanols, alkanols, cycloalkanols, and ethylene glycol) underwent regioselective aerobic cyclocondensation reactions in toluene at 120° to yield substituted quinolines. Kinetic isotope effects and competition reactions using preformed imines and reactions of potential intermediates in the cyclocondensation were used to suggest a mechanism for the reaction. The structure of a cyclobutaquinoline was determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0SDS of cas: 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.SDS of cas: 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

4-Pyrones. 42. Preparation and reactions of 3-acetoacetyl-2-ethoxyquinoxaline was written by Eiden, F.;Bachmann, G.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1973.Formula: C11H9ClN2O2 This article mentions the following:

The quinoxaline I (R = COCH2COMe) (II) was prepared in 83% yield by reaction of I (R = CO2Et) with Me2CO-NaH. Reaction of II with N2H4 yielded 92% I (R = 5-methyl-3-pyrazolyl). Reaction of II with o-(H2N)2C6H4 gave 61% I (R = 2-methyl-1,5-benzodiazepin-4-yl). Reaction of II with PhNHNH2 gave 70% I (R = 1- and 2-phenyl-5-methyl-3-pyrazolyl), reaction of II with HONH2 yielded 75% I (R = 5-methyl-3- and 3-methyl-5-isoxazolyl). The single components of these isomeric mixtures were determined by NMR spectra. 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. 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.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider