7-methyl-3-methylquinoxaline-2-carboxaldehyde-1,4-di-N-oxide | 62018-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-methyl-3-methylquinoxaline-2-carboxaldehyde-1,4-di-N-oxide
• 英文别名: 2-Formyl-3,7-dimethyl-1-oxoquinoxalin-1-ium-4(1H)-olate；3,7-dimethyl-4-oxido-1-oxoquinoxalin-1-ium-2-carbaldehyde
• CAS: 62018-40-0
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: LSAYJXSTLYVOOK-UHFFFAOYSA-N

物化性质

• 熔点：
  163-166 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  476.0±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异烟肼 、 7-methyl-3-methylquinoxaline-2-carboxaldehyde-1,4-di-N-oxide 在 sodium metabisulfite 作用下， 以 四氢呋喃 为溶剂， 生成 7-methyl-3-methyl-1,4-dioxy-quinoxaline-2-ylmethylene hydrazide isonicotinic acid
  参考文献：
  名称：

  New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents

  摘要：

  The increase in the prevalence of drug-resistant tuberculosis cases demonstrates the need of discovering new and promising compounds with antimycobacterial activity. As a continuation of our research and with the aim of identifying new antitubercular drugs candidates, a new series of quinoxaline 1,4-di-N-oxide derivatives containing isoniazid was synthesized and evaluated for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Moreover, various drug-like properties of new compounds were predicted. Taking into account the biological results and the promising drug-likeness profile of these compounds, make them valid leads for further experimental research. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.072
• 作为产物：
  描述：

  7-methyl-2,3-dimethylquinoxaline-1,4-di-N-oxide 在 selenium(IV) oxide 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 7-methyl-3-methylquinoxaline-2-carboxaldehyde-1,4-di-N-oxide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents

  摘要：

  We report the synthesis, anti‐inflammatory, and antioxidant activities of novel quinoxaline and quinoxaline 1,4‐di‐N‐oxide derivatives. Microwave‐assisted methods have been used to optimize reaction times and to improve yields. The tested compounds presented important scavenging activities and promising in vitro inhibition of soybean lipoxygenase (LOX). Two of the best LOX inhibitors (compounds 7b and 8f) were evaluated as in vivo anti‐inflammatory agents using the carrageenin‐induced edema model. One of them (compound 7b) showed important in vivo anti‐inflammatory effect (41%) similar to that of indomethacin (47%) used as the reference drug.

  DOI：

  10.1111/j.1747-0285.2011.01076.x

文献信息

• Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents
  作者：Asunción Burguete、Eleni Pontiki、Dimitra Hadjipavlou-Litina、Saioa Ancizu、Raquel Villar、Beatriz Solano、Elsa Moreno、Enrique Torres、Silvia Pérez、Ignacio Aldana、Antonio Monge

  DOI：10.1111/j.1747-0285.2011.01076.x

  日期：2011.4

  We report the synthesis, anti‐inflammatory, and antioxidant activities of novel quinoxaline and quinoxaline 1,4‐di‐N‐oxide derivatives. Microwave‐assisted methods have been used to optimize reaction times and to improve yields. The tested compounds presented important scavenging activities and promising in vitro inhibition of soybean lipoxygenase (LOX). Two of the best LOX inhibitors (compounds 7b and 8f) were evaluated as in vivo anti‐inflammatory agents using the carrageenin‐induced edema model. One of them (compound 7b) showed important in vivo anti‐inflammatory effect (41%) similar to that of indomethacin (47%) used as the reference drug.
• New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents
  作者：Enrique Torres、Elsa Moreno、Saioa Ancizu、Carlos Barea、Silvia Galiano、Ignacio Aldana、Antonio Monge、Silvia Pérez-Silanes

  DOI：10.1016/j.bmcl.2011.04.072

  日期：2011.6

  The increase in the prevalence of drug-resistant tuberculosis cases demonstrates the need of discovering new and promising compounds with antimycobacterial activity. As a continuation of our research and with the aim of identifying new antitubercular drugs candidates, a new series of quinoxaline 1,4-di-N-oxide derivatives containing isoniazid was synthesized and evaluated for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Moreover, various drug-like properties of new compounds were predicted. Taking into account the biological results and the promising drug-likeness profile of these compounds, make them valid leads for further experimental research. (C) 2011 Elsevier Ltd. All rights reserved.