81321-98-4Relevant articles and documents
Pyridine based polymers. Synthesis and characterization
Pardo, M. A.,Perez, J. M.,Del Valle, M. A.,Godoy, M. A.,Diaz, F. R.
, p. 2464 - 2467 (2014)
Two new conjugated polymers, poly(2,3-di(thiophen-2-yl)pyrido[2,3-b]pyrazine) and poly(2,3-di(thiophen-2-yl)pyrido[3,4-b]pyrazine), based on thiophene and pyridine rings were chemically and electrochemically synthesized and characterized by IR, UV-Vis and
Green Hydrothermal Synthesis of Fluorescent 2,3-Diarylquinoxalines and Large-Scale Computational Comparison to Existing Alternatives
Amaya-García, Fabián,Caldera, Michael,Koren, Anna,Kubicek, Stefan,Menche, J?rg,Unterlass, Miriam M.
, p. 1853 - 1863 (2021/04/02)
Here, the hydrothermal synthesis (HTS) of 2,3-diarylquinoxalines from 1,2-diketones and o-phenylendiamines (o-PDAs) was achieved. The synthesis is simple, fast, and generates high yields, without requiring any organic solvents, strong acids or toxic catalysts. Reaction times down to 90 % in all cases). Moreover, it was shown that HTS has high compatibility: (i) hydrochlorides, a standard commercial form of amines, could be used directly as combined amine source and acidic catalyst, and (ii) Boc-diprotected o-PDA could be directly employed as substrate that underwent HT deprotection. A systematic large-scale computational comparison of all reported syntheses of the presented quinoxalines from the same starting compounds showed that this method is more environmentally friendly and less toxic than all existing methods and revealed generic synthetic routes for improving reaction yields. Finally, the application of the synthesized compounds as fluorescent dyes for cell staining was explored.
Transition Metal-Free Heteroarylation of Quinoxaline: Construction of Heteroaryl-Fused Phenazines by Oxidative Coupling
U?ar, Sefa,Da?tan, Arif
, p. 15502 - 15513 (2020/11/30)
A concise method for the construction of heteroaryl-fused phenazines was developed via PIFA-BF3·Et2O-mediated oxidative coupling of di-heteroarylated quinoxalines for the first time. Synthesis of mono- and di-heteroarylation of quinoxaline was performed effectively using only LiTMP reagent under transition metal-free conditions and without the use of halogen-containing starting compounds. In addition, nonsymmetrical di-heteroarylated quinoxalines were synthesized through reheteroarylation of mono-heteroarylated quinoxalines in the same way. Oxidation of the saturated compounds formed after heteroarylation was easily accomplished with iodine. The UV-vis absorption and fluorescence features of some compounds were examined.
Difuran-substituted quinoxalines as a novel class of PI3Kα H1047R mutant inhibitors: Synthesis, biological evaluation and structure-activity relationship
Zhang, Ning,Yu, Zhimei,Yang, Xiaohong,Zhou, Yan,Tang, Qing,Hu, Ping,Wang, Jia,Zhang, Shao-Lin,Wang, Ming-Wei,He, Yun
, p. 37 - 49 (2018/08/04)
Phosphatidylinositol 3-kinase α (PI3Kα) is the most frequently mutated kinase in human cancers, making it an attractive therapeutic target for cancer treatment. We identified a structurally novel PI3Kα H1047R mutant inhibitor Hit-01 (EC50 = 76.0 μM) through a high-throughput screening campaign. Chemical optimizations enabled us to discover compound 7b, which strongly inhibited PI3Kα H1047R mutant with an EC50 value of 0.137 μM, over 500-fold more potent than Hit-01. Western blotting analysis suggested that 7b could decrease the phosphorylation level of p-AKT, another proof that 7b inhibited PI3Kα H1047R function. Cell viability assay revealed that 7b inhibited HCT116 cancer cell growth with an IC50 value of 11.23 μM. In addition, 7b was found to arrest cell cycle at G1 phase and induce cell apoptosis via up-regulation of caspase-3, caspase-8 and caspase-9 protein expressions. Collectively, all these data demonstrated that 7b could be a promising lead for the development of structurally novel PI3Kα inhibitors.
DNA TARGETED MONO AND HETERODINUCLEAR COMPLEXES
-
Page/Page column 20-21, (2017/07/31)
The invention is related to copper and platin compounds and synthesis method of compounds which are active in cancer cells that show resistance particularly against cisplatin, having a wider effect spectrum in comparison to cisplatin, and a lower toxicity in comparison to cisplatin, having reduced side effects, which can be used as a potential antitumor drug, having anti cancer (cancer treating) and anti oxidant effects, comprising DNA targeted mono and binuclear platin and copper platin complexes and similar functional groups.
One-pot synthesis of quinoxalines from reductive coupling of 2-nitroanilines and 1,2-diketones using indium
Go, Ahra,Lee, Geunsoo,Kim, Jaeho,Bae, Seolhee,Lee, Byung Min,Kim, Byeong Hyo
, p. 1215 - 1226 (2015/03/04)
The one-pot reduction-cyclization of 2-nitroanilines and 1,2-diketones to give quinoxalines was investigated. Using indium and an appropriate acid such as acetic acid or indium(III) chloride, various quinoxaline derivatives including 2,3-dialkylquinoxalines, 2,3-diphenylquinoxalines, 2,3-di-2-thiophenylquinoxalines, 2,3-di(pyridin-2-yl)quinoxalines, and dibenzo[a,c]phenazines were synthesized in moderate to excellent yield.
TMEDA-assisted effective direct ortho arylation of electron-deficient N -heteroarenes with aromatic grignard reagents
Zhuo, Fang-Fang,Xie, Wen-Wen,Yang, Yong-Xin,Zhang, Lei,Wang, Pei,Yuan, Rui,Da, Chao-Shan
, p. 3243 - 3249 (2013/06/26)
In the addition of TMEDA in toluene, aryl Grignards could effectively and site-specifically ortho-arylate electron-deficient heteroarenes under mild conditions. This endeavor successfully changed the old low-yielding reaction, aryl Grignard addition to N-heteroarenes, into an efficient procedure for heterobiaryls. The combination of the inexpensive aryl Grignards, TMEDA, the cost-free air, no use of any transition-metal catalyst, the mild reaction conditions, and the high-yielding gram-scale results enables this new procedure to be cost-effective and potentially utilizable in industry.
One-pot synthesis of quinoxalines starting from aldehydes under metal-free conditions
Hu, Zhong-Yuan,Du, Ding,Tang, Wei-Fang,Lu, Tao
experimental part, p. 2262 - 2264 (2012/08/07)
An efficient and convenient synthesis of quinoxalines from easily available aldehydes was performed as a one-pot procedure in good to excellent yields under metal-free conditions, via sequential benzoin condensation, aerobic formation of benzils and condensation of the latter with 1,2-diaminobenzenes.
A New Type of Reaction between o-Phenylenediamines and Aromatic Aldehydes to Give 2,3-Diarylquinoxalines
Ochoa, Carmen,Rodriguez, Juan
, p. 1053 - 1055 (2007/10/03)
A new type of reaction between o-phenylenediamines and aryl aldehydes at high temperature is reported. The synthesis of 2,3-diarylquinoxalines by this procedure is described.
Protophane und Polyaromaten, XXV. Ringverknuepfende Synthese von Thienyl- und Benzthienylchinoxalinen
Kauffmann, Thomas,Ghanem, Mohammad,Otter, Rolf
, p. 459 - 466 (2007/10/02)
2-(2-Thienyl)- (1a), 2-(3-thienyl)- (2a), and 2,3-di(2-thienyl)quinoxaline (1b), hitherto only accessible by multi-stage ring-forming syntheses, and similar thiophene- and benzothiophene-quinoxaline combinations have been prepared by easily practicable ring-connecting syntheses.Some of the products are favourable starting materials for the synthesis of open-chain polyaromatics and cyclopolyaromatics.
