14003-34-0Relevant academic research and scientific papers
Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides
Carbain, Benoit,Schütznerová, Eva,P?ibylka, Adam,Krchňák, Viktor
, p. 701 - 706 (2016)
We describe a practical (time-efficient, with commercially available building blocks, user friendly reaction conditions, high purity of products) synthesis of pharmacologically relevant quinoxalinones with three points of diversification that takes advantage of solid-phase synthesis and cyclative cleavage. Resin-bound (S)-2-(N-alkyl-2-nitrophenyl)sulfonamide-3-alkyl-N-(2-hydroxyethyl)propanamides, which are accessible from Fmoc-protected α-amino acids, 2-nitrobenzenesulfonyl chloride and alcohols, underwent base-mediated N-arylation. The reduction of the nitro group produced acyclic intermediates that were subjected to acid-mediated cyclative cleavage to yield 3,4-dihydroquinoxalin-2(1H)-ones.
Multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones in an aqueous medium
da Costa, Erivaldo P.,Coelho, Sara E.,de Oliveira, André H.,Araújo, Renata M.,Cavalcanti, Livia N.,Domingos, Josiel B.,Menezes, Fabrício G.
, p. 3961 - 3964 (2018)
A multicomponent synthesis of substituted 3-styryl-1H-quinoxalin-2-ones is described. Sequential reactions of o-phenylenediamine with sodium pyruvate and aldehydes in 20% aqueous acetic acid containing sodium acetate provided the target products in good to high yields. The reaction is proposed to proceed via initial condensation of the diamine and pyruvate partners followed by an aldol condensation-type mechanism.
Design, synthesis, biological evaluation and molecular docking study on peptidomimetic analogues of XK469
Xia, Qiao-Hong,Hu, Wei,Li, Chen,Wu, Ji-Feng,Yang, Liang,Han, Xue-Mei,Shen, Yue-Mao,Li, Zhi-Yu,Li, Xun
, p. 311 - 325 (2016)
XK469 is identified as a potent quinoxaline antineoplastic agent based on its significant clinical efficacy. It probably exerts its activity via DNA topoisomerase II (topo II) inhibition. To obtain more effective antineoplastic agents, a spectrum of peptidomimetic-type quinoxaline analogues of XK469 was herein designed, synthesized, and evaluated. Few compounds (e.g. 13a and 13b) exhibited obvious cytotoxicity indicated by in?vitro anti-proliferative assay. SAR investigation revealed that introducing of hydrophobic tert-butylamine or dodecylamine moiety at the 3-position of quinoxaline core is favorable for achieving a better anti-proliferative potency, while peptidomimetic derivatives only yielded moderate cytotoxicity. Compounds with improved anti-proliferative activities also demonstrated decent anti-metastatic potencies comparable with that of doxorubicin (Doxo) based on in?vivo mouse model study. The topo II-mediated kinetoplast DNA (kDNA) decatenation assay as well as molecular docking studies implicated that these compounds tend to be potent topo II inhibitors. Overall, compounds 13a and 13b, 13b in particular, standed out from various assessments and might be promising candidates for further chemical optimization.
A newly synthesized nitrogen-rich derivative of bicyclic quinoxaline—Structural and conceptual DFT reactivity study
Abad, Nadeem,Hajji, Melek,Ramli, Youssef,Belkhiria, Marwa,Moftah H. Elmgirhi, Salima,A. Habib, Mohamed,Guerfel, Taha,T. Mague, Joel,Essassi, El Mokhtar
, (2020)
Novel nitrogen-rich compound featured bicyclic quinoxaline as a basic core structure has been synthesized, 1-{[1-(3-azido-2-hydroxypropyl)-1H-1,2,3-triazol-4-yl]methyl}-3-methyl-1,2-dihydroquinoxalin-2-one with formula C15H16N8O2, and their structural and chemical reactivity aspects have been comprehensively discussed. Nature, role, and relative contribution of weak noncovalent interactions in supramolecular assembly have been assessed through single-crystal analysis and computational approaches. Useful information about the global and local reactivity were obtained from Conceptual Density Functional Theory at wB97X-D/cc-pVDZ level. Studied system could act as strong electrophile and/or moderate nucleophile in polar organic reactions. We hope this study will provide deeper insight in the knowledge of the synthesis and chemistry of the quinoxaline and quinoxaline derivatives.
Reaction-Based Color-Convertible Fluorescent Probe for Ferroptosis Identification
Shi, Leilei,Guan, Qinghua,Gao, Xihui,Jin, Xin,Xu, Li,Shen, Jian,Wu, Chenwei,Zhu, Xinyuan,Zhang, Chuan
, p. 9218 - 9225 (2018)
Ferroptosis is an iron-mediated, caspase-independent pathway of cell death that is accompanied with the accumulations of reactive oxygen species (ROS) and oxygenases, as well as being involved in many other pathophysiological procedures. However, specific and rapid monitoring of ferroptosis in living cells or tissues has not been achieved so far. Herein, a quinoxalinone-based fluorescent probe (termed as Quinos-4, or QS-4) with a reactive aromatic thioether moiety was designed for ferroptosis identification. Upon exposing it to high levels of ROS and hemeoxygenase-1 (HO-1), which are considered as the biochemical characteristics of ferroptosis, QS-4 could be oxidized into a sulfoxide derivative (QSO-4) and its original aggregation-induced enhanced red fluorescence emission could be converted to green fluorescence emission sharply. On the basis of this unique reaction-induced color conversion, this molecular probe can be employed for identifying the occurrence of ferroptosis both in vitro and in vivo.
Docking of disordered independent molecules of novel crystal structure of (N-(4-methoxyphenyl)-2-(3-methyl-2-oxo-3,4-dihydroquinoxalin-1(2H)-yl)acetamide as anti-COVID-19 and anti-Alzheimer's disease. Crystal structure, HSA/DFT/XRD
Demirta?, Güne?,Mague, Joel T.,Missioui, Mohcine,Ramli, Youssef,Said, Musa A.
, (2022)
New quinoxaline derivative, N-(4-methyl-2-nitrophenyl)-2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide (NMPOQA= disordered molecules NMPOQAa(50.3% and NMPOQAb(49.7%)) has been synthesized and characterized by ESI-MS, IR, 1H &13C NMR. The geometric parameters of NMPOQA compound which crystallographic structure has been defined by X-ray diffraction have been calculated by Density Functional Theory (DFT), B3LYP, 6-311++G(d,p) basis set. The correlation between experimental and theoretical structure was checked by superimposing the experimental and theoretical structure. Frontier Molecular Orbitals (FMO's) have been created and the gap energy between High Occupied Molecular Orbital (HOMO) and Low Unoccupied Molecular Orbital (LUMO) has been calculated. Additionally, Molecular Electrostatic Potential (MEP) and Hirshfeld studies have been conducted to analyze intermolecular interactions. Interesting molecular docking of NMPOQA and Remdesivir drug with 6M03 was conducted using the same parameters for a fair comparison. A low binding affinity of the NMPOQA (?6.9 kcal/mol) compared to the Remdesivir drug, (?7.1 kcal/mol) and other good reasons make NMPOQA a good candidate against COVID-19. A similar study was calculated with 1EVE producing evidences that suggest NMPOQA may serve as a potential drug for developing Alzheimer's disease (AD) treatment
Revisiting the Hinsberg reaction: Facile and expeditious synthesis of 3-substituted quinoxalin-2(1H)-ones under catalyst-free conditions in water
Murthy, Sabbavarapu Narayana,Madhav, Bandaru,Nageswar, Yadavalli Venkata Durga
, p. 1216 - 1220 (2010)
Substituted benzene-1,2-diamine reacted with various α-keto esters at 50° under mild conditions for 15 min using H2O as reaction medium, providing a variety of 3-substituted quinoxalinone derivatives in excellent yields. The reaction was instantaneous, and products were isolated by simple filtration.
Synthesis and Biological Evaluation of 2-Oxo/Thioxoquinoxaline and 2-Oxo/Thioxoquinoxaline-Based Nucleoside Analogues
El-Sayed, Hassan A.,Said, Said A.,Moustafa, Ahmed H.,Baraka, Mohamed M.,Abdel-Kader, Rimaa T.
, p. 16 - 31 (2016)
Several O-and S-quinoxaline glycosides have been prepared by glycosidation of 3-methyl-2-oxo(thioxo)-1,2-dihydroquinoxalines 1a,b with α-D-glucopyranosyl, α-D-galactopyranosyl, and α-D-lactosyl bromide in the presence of K2CO3 followed by deacetylation with Et3N/H2O. Furthermore, alkylation of 1a,b with 4-bromobutyl acetate, 2-acetoxyethoxymethyl bromide, and 3-chloropropanol afforded the corresponding O-and S-acycloquinoxaline nucleosides. Reaction of 1b with chloroacetic acid followed by condensation with sulfacetamide and sulfadiazine in the presence of Et3N/THF and ethyl chloroformate gave the corresponding sulfonamide derivatives 14 and 15, respectively. The structures of new compounds were confirmed by using IR, 1H, 13C NMR spectra and microanalysis. Some of these compounds were screened in vitro for antitumor and antifungal activities.
Synthesis, crystal structure and calculation of oxides of 2-methylamino-3-methyl quinoxaline
Li, Junjian,Wang, Rui,Wang, Wenfeng,Wang, Xucheng,Yuan, Yaofeng,Zhang, Min
, (2020)
Monoxide and dioxide of animo quinoxaline were synthesized and characterized by 1H NMR, 13C NMR and HRMS. The result shows that monoxide is main product. 1H NMR analysis, quantum calculation and crystal structure all indicate that the monoxide is 4-oxide structure but not 1-oxide structure. The subsequent discussions of electronic effect and steric effect of 1-oxide and 4-oxide support the conclusion that 4-oxide is dominant product, which is consistent with 1H NMR analysis and crystal structure. At last, the calculated structure is in good agreement with the crystal structure in this paper, which indicates that the calculation result in this paper is credible.
Crystal structures of 3-methyl-2(1H)-quinoxalinone and three substituted derivatives
Mondieig, Denise,Negrier, Philippe,Massip, Stephane,Leger, Jean Michel,Jarmoumi, Chakir,Lakhrissi, Brahim
, p. 1193 - 1200 (2011)
3-Methyl-2(1H)-quinoxalinone and three derivatives (3,7-dimethyl-2(1H)- quinoxalinone, 3-methyl-6,7-dichloro-2(1H)-quinoxalinone and 3-methyl-7-nitro-2(1H)-quinoxalinone) have been synthesised and analysed by 1H NMR and IR spectral spectroscopies. The crystal structures have been determined at room temperature from X-ray single crystal diffraction data for three of them and from powder diffraction data for the nitro derivative. 3-Methyl-2(1H)-quinoxalinone crystallises in the P21/c monoclinic system, 3,7-dimethyl-2(1H)-quinoxalinone in the Pbca orthorhombic system and the two others compounds in the P1 triclinic system. For the nitro derivative, C-H..N short contacts are established between the carbon of the methyl and the double bounded nitrogen of the ring. For the three other compounds N-H..O hydrogen bonds involve the atoms of the heterocyclic ring. Copyright
