14003-34-0Relevant articles and documents
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.
Synthesis of novel quinoxalines by ring transformation of 3-quinoxalinyl-1,5-benzodiazepine
Kurasawa,Shimabukuro,Okamoto,Takada
, p. 1461 - 1464 (1985)
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Facile synthesis of novel 3-quinoxalinyl-1,5-benzodiazepines via ring transformation. Stable tautomers in the 1,5-benzodiazepin-2-one ring system [1]
Kurasawa,Okamoto,Ogura,Takada
, p. 661 - 664 (1985)
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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.
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Korshak et al.
, (1971)
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Titov,Kozhokina
, p. 1105 (1973)
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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.
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Hoffman,Killinger
, p. 162 (1969)
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Qualitative Profiling of Polyglucose Degradation Products in Peritoneal Dialysis Fluids
Gensberger, Sabrina,Knabner, Carina,Waibel, Reiner,Huppert, Jochen,Pischetsrieder, Monika
, p. 6103 - 6111 (2015)
Heat sterilization of peritoneal dialysis (PD) fluids leads to partial degradation of the osmotic agent to form reactive carbonyl structures, which significantly reduce the biocompatibility of PD fluids and impair long-term PD therapy. Hence, it is important to know the exact composition of the degradation products to improve biocompatibility of PD fluids. Our study conducted targeted screening for degradation products in polyglucose (icodextrin)-containing PD fluids (pGDPs) by applying o-phenylenediamine (OPD) to form stable derivatives, which were analyzed by ultrahigh-performance liquid chromatography with hyphenated diode array tandem mass spectrometry (UHPLC-DAD-MS/MS). For the first time, specific degradation products of polyglucose, namely, 4-deoxyglucosone (4-DG) and 3,4-dideoxypentosone (3,4-DDPS), could be identified in PD fluids. Further, a reaction product of 5-hydroxymethylfurfural (5-HMF) and OPD could be characterized to be (5-(1H-benzo[d]imidazol-2-yl)furan-2-yl)methanol. Additionally, 3-deoxyglucosone (3-DG) and 3-deoxygalactosone (3-DGal), both known to be present in glucose-based PD fluids, were also detected in polyglucose-containing fluids. Trapping a hitherto unknown degradation product with OPD yielded 1,4-bis(1H-benzo[d]imidazol-2-yl)-3,4-dihydroxybutan-1-one, which was present in heat- as well as filter-sterilized PD fluids.
Design, synthesis, molecular modeling and anti-hyperglycemic evaluation of novel quinoxaline derivatives as potential PPARγ and SUR agonists
Ibrahim, Mohammed K.,Eissa, Ibrahim H.,Abdallah, Abdallah E.,Metwaly, Ahmed M.,Radwan,ElSohly
, p. 1496 - 1513 (2017)
In our effort to develop potent anti-hyperglycemic agents with potential agonistic activities toward PPARγ and SUR, three novel series of quinoxaline derivatives bearing sulfonylurea or sulfonylthiourea moieties with different linkers were designed and synthesized. Some of the newly synthesized compounds were evaluated in vivo for their anti-hyperglycemic activities in STZ-induced hyperglycemic rats. Compounds 15a, 15e, 19band 24aexhibited the highest anti-hyperglycemic activities with % reduction in blood glucose level of (50.58, 43.84, 45.10 and 49.62, respectively). Additionally, eight compounds revealed potent anti-hyperglycemic activities were further evaluated in vitro for their PPARγ binding affinity and insulin-secreting ability as potential mechanisms for anti-hyperglycemic activity. Four compounds (15a, 15b, 15dand 15e) significantly bound to PPARγ with IC50values of 0.482, 0.491, 0.350 and 0.369 μM, respectively. Moreover, Compounds 15aand 15bhave demonstrated induction of insulin-secretion with EC50values of 0.92 and 0.98 μM, respectively. Furthermore, molecular docking and pharmacophore generation techniques were carried out to investigate binding patterns and fit values of the designed compounds with PPARγ and SUR, respectively.
Novel antioxidant quinoxaline derivative: Synthesis, crystal structure, theoretical studies, antidiabetic activity and molecular docking study
Missioui, Mohcine,Mortada, Salma,Guerrab, Walid,Serdaro?lu, Goncagül,Kaya, Sava?,Mague, Joel T.,Essassi, El Mokhtar,Faouzi, My El Abbes,Ramli, Youssef
, (2021)
New quinoxaline derivative, N-(4-methyl-2-nitrophenyl)-2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetamide (NPOQA) has been synthesized and characterized by IR, 1H &13C NMR, ESI-MS and single crystal X-ray diffraction analysis using exper
New quinoxaline-2(1H)-ones as potential VEGFR-2 inhibitors: design, synthesis, molecular docking, ADMET profile and anti-proliferative evaluations
Abulkhair, Hamada S.,Eissa, Ibrahim H.,El-Adl, Khaled,ElSohly, Mahmoud A.,Elhendawy, Mostafa A.,Mehany, Ahmed. B. M.,Metwaly, Ahmed M.,Radwan, Mohamed M.,Sakr, Helmy M.,Yousef, Reda G.
, p. 16949 - 16964 (2021/09/27)
Eleven new quinoxaline derivatives were designed and synthesized as modified VEGFR-2 inhibitors of our previous work. The synthesized compounds were tested against three human cancer cell lines (HepG-2, MCF-7 and HCT-116). Compounds11g,11eand11cwere the most potent members against the tested cells. Compound11g(IC50= 4.50, 2.40, and 5.90 μM) was the most potent member compared to doxorubicin (IC50= 8.29, 9.65, and 7.68 μM) and sorafenib (IC50= 7.33, 9.41, and 7.23 μM) against HepG-2 and HCT-116, and MCF-7 cell lines, respectively. Compound11eshowed better anti-proliferative activities than doxorubicin and sorafenib with IC50values of 5.34, 4.19, and 6.06 μM, against HepG-2 and HCT-116 and MCF-7 cell lines, respectively. In addition, the most active anti-proliferative derivatives11c,11e,11f, and11gwere selected to evaluate their inhibitory activities against VEGFR-2. The tested compounds displayed good inhibitory activity with IC50values ranging from 0.75 to 1.36 μM. Among them, compound11gwas the most active member with an IC50value of 0.75 μM, compared to the reference drug; sorafenib (IC50= 1.29 μM). Moreover, docking studies revealed that the synthesized compounds have good binding patterns against the prospective molecular target; VEGFR-2. In addition,in silico, ADMET and toxicity studies showed a high level of drug likeness for the synthesized compounds.
