Heterocyclic Building Blocks-quinoxaline

Aoki, Katsuyuki; Obata, Tatsuhiro; Yamazaki, Yosuke; Mori, Yoshikazu; Hirokawa, Hiroko; Koseki, Jun-ichi; Hattori, Tomohisa; Niitsu, Kazuaki; Takeda, Shuichi; Aburada, Masaki; Miyamoto, Ken-ichi published the artcile< Potent platelet-derived growth factor-β receptor (PDGF-βR) inhibitors: synthesis and structure-activity relationships of 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl}quinoxalin-2(1H)-one derivatives>, Electric Literature of 89898-96-4, the main research area is pyrrolopyridinylquinoxalinone preparation platelet derived growth factor receptor inhibitor.

The authors found previously that 7-[3-(cyclohexylmethyl)ureido]-3-{1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl}quinoxalin-2(1H)-one has considerable potency as a PDGF inhibitor. This compound showed potent inhibitory activity in a PDGF-induced CPA (Cell Proliferation Assay) and APA (Auto-Phosphorylation Assay) (IC50 = 0.05 μmol/l in CPA, 0.03 μmol/l in APA). Therefore, the authors tried to develop a novel and effective PDGF-βR inhibitor by optimizing a series of its derivatives The authors found that trifluoroacetic acid (TFA)-catalyzed coupling of pyrrolo[2,3-b]pyridines with quinoxalin-2-ones proceeded efficiently under mild oxidation condition with manganese(IV) oxide (MnO2) in situ, so this method was applied to prepare a series of derivatives Results of in vitro screening of newly synthesized derivatives identified compound I (R = pentyl) as having potent (IC50 = 0.014 μmol/l in CPA, 0.007 μmol/l in APA) and selective [IC50 values against vascular endothelial growth factor receptor 2 (VEGFR2, kinase domain region, KDR), epidermal growth factor receptor (EGFR), c-Met (hepatocyte growth factor receptor) and insulin growth factor I receptor (IGF-IR)/IC50 against PDGFR were each >1000] inhibitory activity. Moreover, in this series of derivatives, 7-[3-(cyclohexylmethyl)thioureido]-3-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)quinoxalin-2(1H)-one showed potent inhibitory activity toward both PDGF- and VEGF-induced signaling (PDGFR: IC50 = 0.004 μmol/l in CPA, 0.0008 μmol/l in APA, KDR: IC50 = 0.008 μmol/l in APA). Herein, the authors report a new and convenient synthetic method for this series of derivatives and its SAR study.

Chemical & Pharmaceutical Bulletinpublished new progress about Platelet-derived growth factor receptor β Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Electric Literature of 89898-96-4.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Morokata, Tatsuaki; Suzuki, Keiko; Ida, Kenji; Yamada, Toshimitsu published the artcile< Effect of a novel interleukin-5 receptor antagonist, YM-90709, on antigen-induced eosinophil infiltration into the airway of BDF1 mice>, Application of C22H21N3O2, the main research area is YM90709 antiinflammatory IL5 receptor antagonist eosinophil inflammation respiratory tract.

A newly synthesized compound, YM-90709, 2,3-dimethoxy-6,6-dimethyl-5,6-dihydrobenzo[7,8]indolizino[2,3-b]quinoxaline, was previously reported to specifically inhibit the binding of interleukin-5 (IL-5) to its receptor (R) on human eosinophils. In this study, the i.v. injection of YM-90709 inhibited antigen-induced infiltration of eosinophils into the bronchoalveolar lavage fluid (BALF) of BDF1 mice, with an ED50 value of 0.050 mg/kg. Anti-murine IL-5 monoclonal antibody (mAb) also inhibited the infiltration of eosinophils with an ED50 value of 0.035 mg/kg. These results indicate that YM-90709, which is a novel IL-5R antagonist, inhibits antigen-induced eosinophil recruitment into the airway, the same as anti-IL-5 mAb does.

Immunology Letterspublished new progress about Allergic inflammation. 163769-88-8 belongs to class quinoxaline, and the molecular formula is C22H21N3O2, Application of C22H21N3O2.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Liu, Luo-Yan; Qiao, Jennifer X.; Yeung, Kap-Sun; Ewing, William R.; Yu, Jin-Quan published the artcile< meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity>, Related Products of 23088-24-6, the main research area is meta arylation electron rich arene mutually repulsive pyridine ligand; reverse site selectivity alkoxy aromatic compound arylation.

Controlling site selectivity of C-H activation without using a directing group remains a significant challenge. While Pd(II) catalysts modulated by a mutually repulsive pyridine-type ligand have been shown to favor the relatively electron-rich carbon centers of arenes, reversing the selectivity to favor palladation at the relatively electron-deficient positions has not been possible. Herein we report the first catalytic system that effectively performs meta C-H arylation of a variety of alkoxy aromatics including 2,3-dihydrobenzofuran and chroman with exclusive meta site selectivity, thus reversing the conventional site selectivity governed by native electronic effects. The identification of an effective ligand and modified norbornene (NBE-CO2Me), as well as taking advantage of the statistics, are essential for achieving the exclusive meta selectivity.

Journal of the American Chemical Societypublished new progress about Aromatic ethers Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Related Products of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Carrer, Amandine; Brion, Jean-Daniel; Messaoudi, Samir; Alami, Mouad published the artcile< Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)ones with Arylboronic Acids>, Category: quinoxaline, the main research area is palladium catalyst oxidative arylation quinoxalinone arylboronic acid.

A straightforward palladium-catalyzed oxidative C-3 arylation of quinoxalin-2(1H)-ones with arylboronic acids is reported. E.g., in presence of Pd(OAc)2 as catalyst and 1,10-phenanthroline as ligand and O2 as oxidant, arylation of 1-methylquinoxalin-2(1H)-one with 4-MeOC6H4B(OH)2 gave 94% I. This protocol is compatible with a wide range of functional groups and allows construction of various biol. important quinoxalin-2(1H)-one backbones.

Organic Letterspublished new progress about Arylation (oxidative). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Category: quinoxaline.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Long, Xiangdong; Wang, Jia; Gao, Guang; Nie, Chao; Sun, Peng; Xi, Yongjie; Li, Fuwei published the artcile< Direct Oxidative Amination of the Methyl C-H Bond in N-Heterocycles over Metal-Free Mesoporous Carbon>, Category: quinoxaline, the main research area is amide heterocyclic preparation density functional theory kinetic study; heterocycle oxidative amination mesoporous carbon catalyst SAR.

Herein, direct and efficient oxidative amination of the Me C-H bond in a wide range of N-heterocycles such as 2-methylpyridine, 3-methylquinoline, 4-methylpyrimidine, etc. to access the corresponding amides RC(O)NH2 (R = pyridin-2-yl, quinolin-2-yl, 1-methyl-1H-imidazol-2-yl, etc.) over metal-free porous carbon is successfully developed. To understand the fundamental structure-activity relationships of carbon catalysts, the surface functional groups and the graphitization degree of porous carbon have been purposefully tailored through doping with nitrogen or phosphorus. The results of characterization, kinetic studies, liquid-phase adsorption experiments, and theor. calculations indicate that the high activity of the carbon catalyst is attributed to the synergistic effect of surface acidic functional groups (hydroxyl/carboxylic acid/phosphate) and more graphene edge structures exposed on the surface of carbon materials with a high graphitization degree, in which the role of acidic functional groups is to adsorb the substrate mol. and the role of the graphene edge structure is to activate O2.

ACS Catalysispublished new progress about Adsorption energy. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Category: quinoxaline.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Izzo, Francesca Caterina; Vitale, Valentina; Fabbro, Chiara; Van Keulen, Henk published the artcile< Multi-analytical investigation on felt-tip pen inks: Formulation and preliminary photo-degradation study>, Related Products of 5182-90-1, the main research area is photodegradation felt tip pen ink archaeol.

We present a multi-anal. study on the formulation of com. felt-tip pens, introduced in the second half of the 20th century and commonly used by modern and contemporary artists. These media of both drawing and writing have not yet been fully investigated, but the degradation processes they might undergo, such as fading, are well-known and rather apparent.Twelve water-based felt-tip pens were investigated by the joint use of complementary anal. techniques, such as Thin Layer Chromatog., NMR, Fourier transformed IR spectroscopy, X-ray fluorescence spectrometry and Pyrolysis-Gas Chromatog./Mass Spectrometry.The obtained results provided crucial, preliminary data for the identification of dyes, solvents and additives present in the inks’ formulations. Numerous synthetic food coloring agents and pigments were identified, such as Acid Yellow 23, Acid Red 18, Acid Blue 9, and Pigment Blue 15. In addition, glycols, fatty acids, 2-phenoxyethanol, colophony, benzotriazole derivatives and other solvents and additives were detected in the manufactured inks.Furthermore, the effects of photo-degradation on one emblematic ink sample were studied, highlighting in particular visual and aesthetical changes due to discoloration.This study demonstrates a methodol. based upon the use of an integrated anal. approach for the characterization of com. ink-based artistic media and their viable degradation patterns, which aims to develop suitable conservation treatments to assess modern and contemporary drawings and writings.

Microchemical Journalpublished new progress about Archaeology. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Related Products of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Shahin, Mai I.; Abou El Ella, Dalal A.; Ismail, Nasser S. M.; Abouzid, Khaled A. M. published the artcile< Design, synthesis and biological evaluation of type-II VEGFR-2 inhibitors based on quinoxaline scaffold>, Synthetic Route of 6272-25-9, the main research area is arylaminoquinoxalinone arylaminoquinoxaline ureidoarylaminoquinoxaline preparation VEGFR2 inhibitor; structure arylaminoquinoxalinone arylaminoquinoxaline ureidoarylaminoquinoxaline inhibition VEGFR2 kinase; mol docking arylaminoquinoxalinone arylaminoquinoxaline ATP binding site VEGFR2; calculated lipophilicity solubility absorption CYP 2D6 inhibition arylaminoquinoxalinone arylaminoquinoxaline; Docking study; Kinase; Quinoxaline; Type-II; VEGFR-2.

Arylaminoquinoxalinones I [R = HO; R1 = 4-MeOC6H4NH; R2 = R3NHC(:X)NH, 4-R4C6H4SO2NH, 2-HO2CC6H4CONH, MeCONH; R3 = Ph, 3-ClC6H4, 3-MeC6H4, cyclohexyl; R4 = H, Me; X = O, S], arylaminoquinoxalines I [R = H; R1 = 4-R5C6H4NH; R2 = R3NHC(:X)NH, 4-R4C6H4SO2NH, MeCONH; R3 = Ph, 3-MeC6H4, cyclohexyl; R4 = H, Me; R5 = MeO, Cl; X = O, S] and ureidoarylaminoquinoxalines I [R = H; R1 = 4-(3-R6C6H4NHCONH)C6H4NH; R2 = O2N; R6 = H, Cl] were prepared as ATP-competitive VEGFR-2 inhibitors for potential use as antitumor agents. I (R = HO; R1 = 4-MeOC6H4; R2 = PhNHCONH) was the most effective VEGFR-2 inhibitor of the compounds prepared at a concentration of 10 μM. Mol. docking calculations were performed to rationalize the selectivities of quinoxalines for VEGFR-2; calculated physicochem. properties, absorption, and probabilities of CYP 2D6 inhibition were determined for the compounds

Bioorganic Chemistrypublished new progress about Biological permeation. 6272-25-9 belongs to class quinoxaline, and the molecular formula is C8H4ClN3O2, Synthetic Route of 6272-25-9.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Antczak, Christophe; Wee, Boyoung; Radu, Constantin; Bhinder, Bhavneet; Holland, Eric C.; Djaballah, Hakim published the artcile< A High-Content Assay Strategy for the Identification and Profiling of ABCG2 Modulators in Live Cells>, Electric Literature of 163769-88-8, the main research area is ABCG2 protein ABC transporter glioblastoma.

ABCG2 is a member of the ATP-binding cassette (ABC) family of transporters, the overexpression of which has been implicated in resistance to various chemotherapeutic agents. Though a number of cell-based assays to screen for inhibitors have been reported, they do not provide a content-rich platform to discriminate toxic and autofluorescent compounds To fill this gap, we developed a live high-content cell-based assay to identify inhibitors of ABCG2-mediated transport and, at the same time, assess their cytotoxic effect and potential optical interference. We used a pair of isogenic U87MG human glioblastoma cell lines, with one stably overexpressing the ABCG2 transporter. JC-1 (J-aggregate-forming lipophilic cation 5,5′,6,6′-tetrachloro-1,1′,3,3′-tetraethylbenzimidazol carbocyanine iodide) was selected as the optimal reporter substrate for ABCG2 activity, and the resulting assay was characterized by a Z’ value of 0.50 and a signal-to-noise (S/N) ratio of 14 in a pilot screen of ∼7,000 diverse chems. The screen led to the identification of 64 unique nontoxic positives, yielding an initial hit rate of 1%, with 58 of them being confirmed activity. In addition, treatment with two selected confirmed positives suppressed the side population of U87MG-ABCG2 cells that was able to efflux the Hoechst dye as measured by flow cytometry, confirming that they constitute potent new ABCG2 transporter inhibitors. Our results demonstrate that our live cell and content-rich platform enables the rapid identification and profiling of ABCG2 modulators, and this new strategy opens the door to the discovery of compounds targeting the expression and/or trafficking of ABC transporters as an alternative to functional inhibitors that failed in the clinic.

Assay and Drug Development Technologiespublished new progress about Antioxidants. 163769-88-8 belongs to class quinoxaline, and the molecular formula is C22H21N3O2, Electric Literature of 163769-88-8.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Zhang, Zhongxing; Yin, Zhiwei; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao published the artcile< Azole-N-acetonitriles as carbonyl synthons: A one-pot preparation of heteroaryl amides from halides>, Name: Quinoxaline-2-carboxamide, the main research area is heteroaryl amide preparation; halo heterocycle reaction azole acetonitrile oxidation amine displacement.

Azole-N-acetonitrile derivatives were utilized as synthons for an ambident carbonyl moiety via a strategy relying upon sequential base-mediated SNAr substitution of a 2-halo heterocycle, in situ oxidation, and amine displacement. This strategy allows prompt and efficient synthesis of N-containing heteroaryl amides directly from the corresponding halides via a one-pot process. E.g., reaction of 2-halo heterocycle I (R = Cl) with azole-N-acetonitrile derivative II, followed by reaction with Me2NH and oxidation with peracetic acid, gave 69% heteroaryl amide I (R = NMe2).

Synlettpublished new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation) (heteroaryl). 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Name: Quinoxaline-2-carboxamide.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Climent, M. J.; Corma, A.; Hernandez, J. C.; Hungria, A. B.; Iborra, S.; Martinez-Silvestre, S. published the artcile< Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts>, Related Products of 23088-24-6, the main research area is vicinal diol phenylenediamine gold nanoparticle oxidation cyclocondensation catalyst; dinitrobenzene vicinal diol gold nanoparticle reduction oxidation cyclocondensation catalyst; quinoxaline preparation.

An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to α-hydroxycarbonyl compound Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product.

Journal of Catalysispublished new progress about Aromatic diamines Role: RCT (Reactant), RACT (Reactant or Reagent). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Related Products of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider