N¹-(4-chloro-6-(piperidin-1-yl)-1,3,5-triazin-2-yl)-N⁴-(7-chloroquinolin-4-yl)benzene-1,4-diamine | 1269458-09-4

• 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: N¹-(4-chloro-6-(piperidin-1-yl)-1,3,5-triazin-2-yl)-N⁴-(7-chloroquinolin-4-yl)benzene-1,4-diamine
• 英文别名: N-(4-chloro-6-piperidin-1-yl-[1,3,5]triazin-2-yl)-N'-(7-chloro-quinolin-4-yl)-benzene-1,4-diamine；4-N-(4-chloro-6-piperidin-1-yl-1,3,5-triazin-2-yl)-1-N-(7-chloroquinolin-4-yl)benzene-1,4-diamine
• CAS: 1269458-09-4
• 化学式: C₂₃H₂₁Cl₂N₇
• 分子量: 466.373
• InChiKey: XCATVRPSDOHGTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(3-氨丙基)吗啉 、 N¹-(4-chloro-6-(piperidin-1-yl)-1,3,5-triazin-2-yl)-N⁴-(7-chloroquinolin-4-yl)benzene-1,4-diamine 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以87%的产率得到N-[4-(7-chloro-quinolin-4-ylamino)-phenyl]-N'-(3-morpholin-4-yl-propyl)-6-piperidin-1-yl-[1,3,5]triazine-2,4-diamine
  参考文献：
  名称：

  4-Anilinoquinoline triazines: A novel class of hybrid antimalarial agents

  摘要：

  A novel class of hybrid 4-anilinoquinoline triazines have been synthesized and evaluated in vitro for their antimalarial activity against CQ-sensitive 3D7 strain of P. falciparum as well as for their cytotoxicity toward VERO cell line. Five compounds (19, 20, 23, 41 and 45) exhibited the antimalarial potency superior to CQ. Compounds 14 and 16 were found to be orally active at a dose of 100 mg/kg x 4 days against CQ-resistant strain of P. yoelii. Inhibition of (beta-hematin formation assay and molecular docking study has been conducted in order to gain insight into the mechanism of action of proposed targets for the 4-anilinoquinoline and triazine moiety of the hybrid compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.003
• 作为产物：
  描述：

  对苯二胺 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 N¹-(4-chloro-6-(piperidin-1-yl)-1,3,5-triazin-2-yl)-N⁴-(7-chloroquinolin-4-yl)benzene-1,4-diamine
  参考文献：
  名称：

  新的4-苯胺基喹啉衍生物的对接，合成和抗疟活性。

  摘要：

  设计，合成和筛选了一系列4-苯胺基喹啉三嗪衍生物，它们对氯喹敏感的伯氏疟原虫菌株具有体内抗疟活性。这些化合物进一步经受了针对恶性疟原虫抗氯喹W2菌株的体外抗疟活性和β-血红素抑制研究。与标准药物氯喹相比，所有化合物均表现出更好的体内抗疟活性。在15种化合物中，有12种对恶性疟原虫的耐氯喹W2菌株表现出比氯喹更好的抑制作用。十种化合物对β-血红素的抑制作用优于氯喹，IC50值在18-25μM的范围内。一种化合物3k

  DOI：

  10.1016/j.bmcl.2017.03.005

文献信息

• 4-Anilinoquinoline triazines: A novel class of hybrid antimalarial agents
  作者：Ashok Kumar、Kumkum Srivastava、S. Raja Kumar、M.I. Siddiqi、Sunil K. Puri、Jitendra K. Sexana、Prem M.S. Chauhan

  DOI：10.1016/j.ejmech.2010.12.003

  日期：2011.2

  A novel class of hybrid 4-anilinoquinoline triazines have been synthesized and evaluated in vitro for their antimalarial activity against CQ-sensitive 3D7 strain of P. falciparum as well as for their cytotoxicity toward VERO cell line. Five compounds (19, 20, 23, 41 and 45) exhibited the antimalarial potency superior to CQ. Compounds 14 and 16 were found to be orally active at a dose of 100 mg/kg x 4 days against CQ-resistant strain of P. yoelii. Inhibition of (beta-hematin formation assay and molecular docking study has been conducted in order to gain insight into the mechanism of action of proposed targets for the 4-anilinoquinoline and triazine moiety of the hybrid compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Docking, synthesis and antimalarial activity of novel 4-anilinoquinoline derivatives
  作者：Shilpa Vijayaraghavan、Supriya Mahajan

  DOI：10.1016/j.bmcl.2017.03.005

  日期：2017.4

  4-anilinoquinoline triazine derivatives were designed, synthesized and screened for in vivo antimalarial activity against a chloroquine-sensitive strain of Plasmodium berghei. The compounds were further subjected to in vitro antimalarial activity against chloroquine-resistant W2 strain of Plasmodium falciparum and β-haematin inhibition studies. All the compounds exhibited in vivo antimalarial activity better than

  设计，合成和筛选了一系列4-苯胺基喹啉三嗪衍生物，它们对氯喹敏感的伯氏疟原虫菌株具有体内抗疟活性。这些化合物进一步经受了针对恶性疟原虫抗氯喹W2菌株的体外抗疟活性和β-血红素抑制研究。与标准药物氯喹相比，所有化合物均表现出更好的体内抗疟活性。在15种化合物中，有12种对恶性疟原虫的耐氯喹W2菌株表现出比氯喹更好的抑制作用。十种化合物对β-血红素的抑制作用优于氯喹，IC50值在18-25μM的范围内。一种化合物3k