4-(4-methoxyphenyl)-3H-pyrrolo[2,3-c]quinoline | 1393936-03-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-(4-methoxyphenyl)-3H-pyrrolo[2,3-c]quinoline
• 英文别名: 4-(4-Methoxyphenyl)-3H-pyrrolo[2,3-c]quinoline
• CAS: 1393936-03-2
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: WVUFPJWZKOQPSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-nitrobenzenediazonium tetrafluoroborate 在 2,6-二甲基吡啶 、 palladium 10% on activated carbon 、 水 、 氢气 、 palladium diacetate 、 magnesium sulfate 、 三氟乙酸 、 三氟乙酸酐 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， -50.0~150.0 ℃ 、101.33 kPa 条件下， 反应 12.67h， 生成 4-(4-methoxyphenyl)-3H-pyrrolo[2,3-c]quinoline
  参考文献：
  名称：

  Divergent total synthesis of the natural antimalarial marinoquinolines A, B, C, E and unnatural analogues

  摘要：

  A new synthetic route to marinoquinolines was developed, allowing the synthesis of several structurally related compounds from a common key intermediate. Four natural marinoquinolines (A, B. C and E) and nine unnatural new analogues were prepared by this strategy, which features a Heck-Matsuda reaction in pure water and the Pictet-Spengler reaction as key steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.115

文献信息

• Discovery of Marinoquinolines as Potent and Fast-Acting <i>Plasmodium falciparum</i> Inhibitors with in Vivo Activity
  作者：Anna Caroline Campos Aguiar、Michele Panciera、Eric Francisco Simão dos Santos、Maneesh Kumar Singh、Mariana Lopes Garcia、Guilherme Eduardo de Souza、Myna Nakabashi、José Luiz Costa、Célia R. S. Garcia、Glaucius Oliva、Carlos Roque Duarte Correia、Rafael Victorio Carvalho Guido

  DOI：10.1021/acs.jmedchem.8b00143

  日期：2018.7.12

  We report the discovery of marinoquinoline (3H-pyrrolo[2,3-c]quinoline) derivatives as new chemotypes with antiplasmodial activity. We evaluated their inhibitory activities against P. falciparum and conducted a structure–activity relationship study, focusing on improving their potency and maintaining low cytotoxicity. Next, we devised quantitative structure–activity relationship (QSAR) models, which

  我们报告了marinoquinoline（3 H -pyrrolo [2,3- c ] quinoline）衍生物作为具有抗血浆活性的新化学型的发现。我们评估了它们对恶性疟原虫的抑制活性，并进行了结构-活性关系研究，重点是提高其效力并保持低细胞毒性。接下来，我们设计了定量结构-活性关系（QSAR）模型，该模型经过前瞻性验证，以发现具有增强效价的新类似物。最有效的化合物50（IC 50 3d7 = 39 nM; IC 50 K1= 41 nM），是一种具有双阶段（血液和肝脏）活性的速效抑制剂。该化合物显示出相当高的选择性（SI> 6410），与青蒿琥酯组合使用时具有累加作用，对小鼠具有出色的耐受性（所有小鼠在口服1000 mg / kg剂量后均存活）和50 mg / kg的口服功效在伯氏疟原虫疟疾的小鼠模型中（感染后第5天寄生虫病减少62％）；因此，化合物50被认为是发现新抗疟药的主要化合物。
• New class of antitubercular compounds: synthesis and anti-tubercular activity of 4-substituted pyrrolo[2,3-c]quinolines
  作者：Mahesh Akula、Jonnalagadda Padma Sridevi、P. Yogeeswari、D. Sriram、Anupam Bhattacharya

  DOI：10.1007/s00706-013-1141-1

  日期：2014.5

  AbstractModified synthesis and antitubercular activity of 4-substituted pyrrolo[2,3-c]quinolines are reported. Some of the compounds showed significant antitubercular activity, when compared to some of the existing antitubercular drugs. A compound with an imidazole moiety at position 4 shows the highest activity and least toxicity. Graphical abstract

  摘要报道了4-取代的吡咯并[2,3- c ]喹啉的合成和抗结核活性。与某些现有的抗结核药物相比，某些化合物具有显着的抗结核活性。在4位具有咪唑部分的化合物显示出最高的活性和最低的毒性。 图形概要
• Divergent total synthesis of the natural antimalarial marinoquinolines A, B, C, E and unnatural analogues
  作者：Cristiane Storck Schwalm、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2012.06.115

  日期：2012.9

  A new synthetic route to marinoquinolines was developed, allowing the synthesis of several structurally related compounds from a common key intermediate. Four natural marinoquinolines (A, B. C and E) and nine unnatural new analogues were prepared by this strategy, which features a Heck-Matsuda reaction in pure water and the Pictet-Spengler reaction as key steps. (C) 2012 Elsevier Ltd. All rights reserved.