ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide | 57859-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide
• 英文别名: 2-(ethoxycarbonyl)-3-phenylquinoxaline 1,4-dioxide；2-(Carboethoxy)-3-phenylquinoxaline 1,4-Dioxide；1,4-dioxy-3-phenyl-quinoxaline-2-carboxylic acid ethyl ester；2-(carboethoxy)-3-phenylquinoxaline-1,4-dioxide；Ethyl 1-oxido-4-oxo-3-phenylquinoxalin-4-ium-2-carboxylate
• CAS: 57859-60-6
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: ACCMCHSYOAMMEV-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C(Solv: ethanol (64-17-5))
• 沸点：
  551.7±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide 在 sodium hydroxide 、 三甲氧基磷 作用下， 以 丙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 2-Phenylchinoxalin-1-oxid
  参考文献：
  名称：

  Formation of quinoxaline monoxides from reaction of benzofurazan oxide with enones and carbon-13 NMR correlations of quinoxaline N-oxides

  摘要：

  DOI：

  10.1021/jo01298a030
• 作为产物：
  描述：

  苯并呋咱 、 苯甲酰乙酸乙酯 在 Wako gel C-200 作用下， 反应 168.0h， 以63%的产率得到ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide
  参考文献：
  名称：

  Reactions of Benzofuroxan with 1,3-Diketones or β-Ketoesters on Silica Gel or Alumina

  摘要：

  苯并呋咱氧化物与1,3-二酮、3-氧代烷酸酯、丁二酸酯或3-氧代烷酰胺在硅胶存在下的环化缩合反应（各组分吸附在硅胶上），代表了一种合成2,3-二取代喹喔啉-1,4-二氧化物的简便方法。

  DOI：

  10.1055/s-1985-31391

文献信息

• Comparative use of solvent-free KF-A1₂O₃and K₂CO₃in acetone in the synthesis of quinoxaline 1,4-dioxide derivatives designed as antimalarial drug candidates
  作者：L. M. Lima、B. Zarranz、A. Marin、B. Solano、E. Vicente、S. Perez Silanes、I. Aldana、A. Monge

  DOI：10.1002/jhet.5570420718

  日期：2005.11

  paper we describe two new basic conditions for the synthesis of quinoxaline 1,4-dioxide derivatives in moderate to good yields. These conditions, exemplified by the use of K2C03 in acetone or KF/A1203 in the absence of an organic solvent, were reproducible and applicable to the synthesis of 2-(carboethoxy)-3-phenylquinoxaline 1,4-dioxide derivatives substituted in position 4 with electron-donating or

  在本文中，我们描述了以中等到良好的产率合成喹喔啉1,4-二氧化物衍生物的两个新的基本条件。这些条件下，通过使用的K例举2 C0 3在丙酮或KF / Al 2 0 3在不存在有机溶剂的，是可再现的并且适用于2-（乙氧羰基）-3-苯基喹喔啉的合成1,4-在4位上被给电子或吸电子基团取代的二氧化碳衍生物。
• Unexpected Reduction of Ethyl 3-Phenylquinoxaline-2- carboxylate 1,4-Di-N-oxide Derivatives by Amines
  作者：Lidia Lima、Esther Vicente、Beatriz Solano、Silvia Pérez-Silanes、Ignacio Aldana、Antonio Monge

  DOI：10.3390/molecules13010078

  日期：——

  The unexpected tendency of amines and functionalized hydrazines to reduceethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide (1) to afford a quinoxaline 1c andmono-oxide quinoxalines 1a and 1b is described. The experimental conditions werestandardized to the use of two equivalents of amine in ethanol under reflux for two hours,with the aim of studying the distinct reductive profiles of the amines and thechemoselectivity of the process. With the exception of hydrazine hydrate, which reducedcompound 1 to a 3-phenyl-2-quinoxalinecarbohydrazide derivative, the amines only actedas reducing agents.

  本文描述了胺和官能化肼在还原 3-苯基喹喔啉-2-甲酸乙酯 1,4-二-N-氧化物（1）时产生喹喔啉 1c 和单氧化物喹喔啉 1a 和 1b 的意想不到的趋势。我们将实验条件标准化为在乙醇中使用两当量的胺，并回流两小时，目的是研究胺的不同还原性特征以及该过程的化学选择性。除了将化合物 1 还原成 3-苯基-2-喹喔啉羧酰肼衍生物的水合肼之外，其他胺都只起还原剂的作用。
• Selective activity against Mycobacterium tuberculosis of new quinoxaline 1,4-di-N-oxides
  作者：Esther Vicente、Silvia Pérez-Silanes、Lidia M. Lima、Saioa Ancizu、Asunción Burguete、Beatriz Solano、Raquel Villar、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.bmc.2008.10.086

  日期：2009.1

  New series of 3-phenylquinoxaline 1,4-di-N-oxide with selective activity against Mycobacterium tuberculosis have been prepared and evaluated. Thirty-four of the seventy tested compounds showed an MIC value less than 0.2 mu g/mL, a value on the order of the MIC of rifampicin. Furthermore, 45% of the evaluated derivatives showed a good in vitro activity/toxicity ratio. The most active and selective compounds carry a fluorine atom in the quinoxaline 7-position or in the phenyl substituent para-position. In conclusion, the potency, low cytotoxicity and selectivity of these compounds make them valid lead compounds for synthesizing new analogues, particularly compound 7-methyl-3-(4'-fluoro) phenylquinoxaline-2-carbonitrile 1,4-di-N-oxide (MIC <0.2 mu g/mL and SI > 500). (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents
  作者：Esther Vicente、Lidia M. Lima、Emily Bongard、Sarah Charnaud、Raquel Villar、Beatriz Solano、Asunción Burguete、Silvia Perez-Silanes、Ignacio Aldana、Livia Vivas

  DOI：10.1016/j.ejmech.2007.11.024

  日期：2008.9

  As a continuation of our research and with the aim of obtaining new antimalarial agents, new series of 3-phenylquinoxaline 1,4-di-N-oxide derivatives have been synthesized following the classical Beirut reaction. Antiplasmodial activity was evaluated in vitro against Plasmodium falciparum by the incorporation of [H-3]-hypoxanthine. Cytotoxicity was tested in KB cells by AlamarBlue assay. Twenty-one of the 60 compounds that were assayed against 3D7 (CQ-sensitive) showed enough activity to be also evaluated against K1 (CQ-resistant) strain. Ten of them were shown to be more active than chloroquine in the resistant strain. The most interesting compounds are 7-(methyl or methoxy)-3-(4'-fluoro or chloro)phenylquinoxaline-2-carbonitrile 1,4-di-N-oxides because of their low IC50 and their high SI shown for the K1 strain, making them valid new leads. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis, trypanocidal activity and docking studies of novel quinoxaline-N-acylhydrazones, designed as cruzain inhibitors candidates
  作者：Nelilma C. Romeiro、Gabriela Aguirre、Paola Hernández、Mercedes González、Hugo Cerecetto、Ignacio Aldana、Silvia Pérez-Silanes、Antonio Monge、Eliezer J. Barreiro、Lídia M. Lima

  DOI：10.1016/j.bmc.2008.11.065

  日期：2009.1

  In this paper, we report the structural design, synthesis, trypanocidal activity and docking studies of novel quinoxaline-N-acylhydrazone (NAH) derivatives, planned as cruzain inhibitors candidates, a cysteine protease essential for the survival of Trypanosoma cruzi within the host cell. The salicylaldehyde N-acylhydrazones 7a and 8a presented IC(50) values of the same magnitude order than the standard drug nifurtimox (Nfx), when tested in vitro against epimastigote forms of Trypanosoma cruzi (Tulahuen 2 strain) and were non-toxic at the highest assayed doses rendering selectivity indexes (IC(50) (macrophages)/IC(50) (Trypanosoma cruzi)) of > 25 for 7a and > 20 for 8a, with IC(50) values in macrophages > 400 mu M. (C) 2008 Elsevier Ltd. All rights reserved.