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
Antiplasmodial 2-thiophenoxy-3-trichloromethyl quinoxalines target the apicoplast of Plasmodium falciparum
Amanzougaghene, Nadia,Amrane, Dyhia,Azas, Nadine,Azqueta, Amaya,Mazier, Dominique,Primas, Nicolas,Sanz-Serrano, Julen,Tajeri, Shahin,Vanelle, Patrice,Verhaeghe, Pierre,Arnold, Christophe-Sébastien,Botté, Cyrille,Hutter, Sébastien,Louis, Béatrice
, (2021/08/09)
The identification of a plant-like Achille's Heel relict, i.e. the apicoplast, that is essential for Plasmodium spp., the causative agent of malaria lead to an attractive drug target for new antimalarials with original mechanism of action. Although it is not photosynthetic, the apicoplast retains several anabolic pathways that are indispensable for the parasite. Based on previously identified antiplasmodial hit-molecules belonging to the 2-trichloromethylquinazoline and 3-trichloromethylquinoxaline series, we report herein an antiplasmodial Structure-Activity Relationships (SAR) study at position two of the quinoxaline ring of 16 newly synthesized compounds. Evaluation of their activity toward the multi-resistant K1 Plasmodium falciparum strain and cytotoxicity on the human hepatocyte HepG2 cell line revealed a hit compound (3k) with a PfK1 EC50 value of 0.3 μM and a HepG2 CC50 value of 56.0 μM (selectivity index = 175). Moreover, hit-compound 3k was not cytotoxic on VERO or CHO cell lines and was not genotoxic in the in vitro comet assay. Activity cliffs were observed when the trichloromethyl group was replaced by CH3, CF3 or H, showing that this group played a key role in the antiplasmodial activity. Biological investigations performed to determine the target and mechanism of action of the compound 3k strongly suggest that the apicoplast is the putative target as showed by severe alteration of apicoplaste biogenesis and delayed death response. Considering that there are very few molecules that affect the Plasmodium apicoplast, our work provides, for the first time, evidence of the biological target of trichloromethylated derivatives.
Active photosensitizer and preparation method and application thereof
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Paragraph 0011; 0036-0038, (2021/10/16)
The invention provides a quinoxalinone active photosensitizer based on histone deacetylase as a target and a preparation method and application thereof. Nucleophilic substitution, aldol condensation The reaction is obtained by a hydroxylamine solution or the like. The compounds of the invention can significantly inhibit HDAC1, 6, 8 activity, IC50 respectively 89 ±4.6, 34 ±2.7 and 852 ± 6 . 3nM, and the compound generates a large amount of active oxygen radicals under irradiation of 450 nm lasers, and can be used as a potential active photosensitizer. The compound can be directly added into a culture medium and then used for photodynamic binding molecule targeted therapy of breast cancer cells (MCF-7), and can also be used for intravenous injection after nano particles. Power therapy.
