1-(7-Methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-ethanone | 356579-30-1

• 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: 1-(7-Methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-ethanone
• 英文别名: 1-(7-Methoxy-3-methyl-1,4-dioxido-quinoxaline-1,4-diium-2-yl)ethanone；1-(7-methoxy-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)ethanone
• CAS: 356579-30-1
• 化学式: C₁₂H₁₂N₂O₄
• mdl: MFCD02642947
• 分子量: 248.238
• InChiKey: YVMROIPMRPBCTR-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C(Solv: methanol (67-56-1))
• 沸点：
  487.1±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-(7-Methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-ethanone 在 sodium dithionite 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.33h， 生成 4-[3-(7-methoxy-3-methylquinoxalin-2-yl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydropyrazol-1-yl]benzenesulfonamide
  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
• 作为产物：
  描述：

  5-甲氧基苯并呋喃 3-氧化物 、 乙酰丙酮 在 2-氨基乙醛 、 calcium chloride 作用下， 生成 1-(7-Methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-ethanone
  参考文献：
  名称：

  Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents

  摘要：

  我们报道了十八种喹喔啉和喹喔啉1,4-双-N-氧化物衍生物的合成及其抗疟活性，其中八种是完全新颖的。化合物1a和2a对恶性�隆疟原虫株表现出最强的活性。结构-活性关系表明，与喹喔啉环相连的烯酮部分的重要性。

  DOI：

  10.3390/molecules19022166

文献信息

• Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents
  作者：Andrés Jaso、Belén Zarranz、Ignacio Aldana、Antonio Monge

  DOI：10.1016/s0223-5234(03)00137-5

  日期：2003.9

  A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC90/MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides
  作者：Kamelia M. Amin、Magda M.F. Ismail、Eman Noaman、Dalia H. Soliman、Yousry A. Ammar

  DOI：10.1016/j.bmc.2006.06.038

  日期：2006.10

  Hypoxic cells which are common feature of solid tumors are resistant to both anticancer drugs and radiation therapy. Thus, the identification of drugs with the selective toxicity toward hypoxic cells is an important target in anticancer chemotherapy. Tirapazamine has been shown to be an efficient and selective cytotoxin after bioreductive activation in hypoxic cells which is thought to be due to the presence of the 1,4-di-N-oxide. A new series of quinoxaline 1,4-di-N-oxides and fused quinoxaline di-N-oxides were synthesized and evaluated for hypoxic-cytotoxic activity on EAC cell line. Compound 10a was the most potent cytotoxin IC50 0.9 mu g/mL, potency 75 mu g/mL, and was approximately 15 times more selective cytotoxin (HCR > 111) than 3-aminoquinoxaline-2-carbonitrile which has been used as a standard (HCR > 7.5). Compounds 4 and 3a,b were more selective than the standard. In addition, antitumor activity against Hepg2 (liver) and U251 (brain) human cell lines was evaluated, compounds 9c and 8a were the most active against Hepg2 with IC50 values 1.9 and 2.9 mu g/mL, respectively, however, all the tested compounds were nontoxic against U251 cell line. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and anti-inflammatory/antioxidant activities of some new ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues
  作者：Asunción Burguete、Eleni Pontiki、Dimitra Hadjipavlou-Litina、Raquel Villar、Esther Vicente、Beatriz Solano、Saioa Ancizu、Silvia Pérez-Silanes、Ignacio Aldana、Antonio Monge

  DOI：10.1016/j.bmcl.2007.10.002

  日期：2007.12

  We report the synthesis, anti-inflammatory and antioxidant activities of novel ring substituted 3-phenyl-1-(1,4-di-N-oxide quinoxalin-2-yl)-2-propen-1-one derivatives and of their 4,5-dihydro-(1H)-pyrazole analogues. The tested compounds inhibit the carrageenin-induced rat paw edema (4.5-56.1%) and present important scavenging activities. Compound 2a is the most potent (56.1%) in the in vivo experiment and exhibits promising in vitro inhibition of soybean lipoxygenase (IC50 < 1 mu M). (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents
  作者：Ana Gil、Adriana Pabón、Silvia Galiano、Asunción Burguete、Silvia Pérez-Silanes、Eric Deharo、Antonio Monge、Ignacio Aldana

  DOI：10.3390/molecules19022166

  日期：——

  We report the synthesis and antimalarial activities of eighteen quinoxaline and quinoxaline 1,4-di-N-oxide derivatives, eight of which are completely novel. Compounds 1a and 2a were the most active against Plasmodium falciparum strains. Structure-activity relationships demonstrated the importance of an enone moiety linked to the quinoxaline ring.

  我们报道了十八种喹喔啉和喹喔啉1,4-双-N-氧化物衍生物的合成及其抗疟活性，其中八种是完全新颖的。化合物1a和2a对恶性�隆疟原虫株表现出最强的活性。结构-活性关系表明，与喹喔啉环相连的烯酮部分的重要性。
• 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.