(2E)-1-(3-methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)propenone | 1301603-45-1

• 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: (2E)-1-(3-methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)propenone
• 英文别名: 1-(3-Methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-1-(3-methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1301603-45-1
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: FPHBGZHKACEKOU-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-1-(3-methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)propenone 、 4-磺酰胺基苯肼盐酸盐 以 乙醇 为溶剂， 反应 0.33h， 以14%的产率得到4-[3-(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：

  苯并呋咱 在 2-氨基乙醛 、 calcium chloride 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (2E)-1-(3-methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)propenone
  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, 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.