6-chloro-N2-(4-((6-chloro-2-methoxyacridin-9-yl)amino)phenyl)-N4-(4-fluorophenyl)-1,3,5-triazine-2,4-diamine | 1203487-94-8

• 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: 6-chloro-N2-(4-((6-chloro-2-methoxyacridin-9-yl)amino)phenyl)-N4-(4-fluorophenyl)-1,3,5-triazine-2,4-diamine
• CAS: 1203487-94-8
• 化学式: C₂₉H₂₀Cl₂FN₇O
• 分子量: 572.429
• InChiKey: IBUWTIIJKGETAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  96.88
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-chloro-N2-(4-((6-chloro-2-methoxyacridin-9-yl)amino)phenyl)-N4-(4-fluorophenyl)-1,3,5-triazine-2,4-diamine 在 氨 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-N-[4-[(6-chloro-2-methoxyacridin-9-yl)amino]phenyl]-2-N-(4-fluorophenyl)-1,3,5-triazine-2,4,6-triamine
  参考文献：
  名称：

  Synthesis of 9-anilinoacridine triazines as new class of hybrid antimalarial agents

  摘要：

  There is challenge and urgency to synthesize cost-effective chemotherapeutic agents for treatment of malaria after the widespread development of resistance to CQ. In the present study, we synthesized a new series of hybrid 9-anilinoacridine triazines using the cheap chemicals 6,9-dichloro-2-methoxy acridine and cyanuric chloride. The series of new hybrid 9-anilinoacridine triazines were evaluated in vitro for their antimalarial activity against CQ-sensitive 3D7 strain of Plasmodium falciparum and their cytotoxicity were determined on VERO cell line. Of the evaluated compounds, two compounds 17 (IC50 = 4.21 nM) and 22 (IC50 = 4.27 nM) displayed two times higher potency than CQ (IC50 = 8.15 nM). Most of the compounds showed fairly high selectivity index. The compounds 13 and 29 displayed > 96.59% and 98.73% suppression, respectively, orally against N-67 strain of Plasmodium yoelii in swiss mice at dose 100 mg/kg for four days. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.010
• 作为产物：
  描述：

  N-(6-chloro-2-methoxy-acridin-9-yl)-benzene-1,4-diamine 、 2,4-二氯-6-(4-氟苯胺基)-1,3,5-三嗪 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 6-chloro-N2-(4-((6-chloro-2-methoxyacridin-9-yl)amino)phenyl)-N4-(4-fluorophenyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  Synthesis of 9-anilinoacridine triazines as new class of hybrid antimalarial agents

  摘要：

  There is challenge and urgency to synthesize cost-effective chemotherapeutic agents for treatment of malaria after the widespread development of resistance to CQ. In the present study, we synthesized a new series of hybrid 9-anilinoacridine triazines using the cheap chemicals 6,9-dichloro-2-methoxy acridine and cyanuric chloride. The series of new hybrid 9-anilinoacridine triazines were evaluated in vitro for their antimalarial activity against CQ-sensitive 3D7 strain of Plasmodium falciparum and their cytotoxicity were determined on VERO cell line. Of the evaluated compounds, two compounds 17 (IC50 = 4.21 nM) and 22 (IC50 = 4.27 nM) displayed two times higher potency than CQ (IC50 = 8.15 nM). Most of the compounds showed fairly high selectivity index. The compounds 13 and 29 displayed > 96.59% and 98.73% suppression, respectively, orally against N-67 strain of Plasmodium yoelii in swiss mice at dose 100 mg/kg for four days. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.010