5-chloro-6-methoxy-4-methyl-8-nitro-2-trifluoromethyl-quinoline | 1260253-65-3

• 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: 5-chloro-6-methoxy-4-methyl-8-nitro-2-trifluoromethyl-quinoline
• 英文别名: 5-Chloro-6-methoxy-4-methyl-8-nitro-2-(trifluoromethyl)quinoline
• CAS: 1260253-65-3
• 化学式: C₁₂H₈ClF₃N₂O₃
• 分子量: 320.655
• InChiKey: BKKHWEFLLVCZSN-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-chloro-6-methoxy-4-methyl-8-nitro-2-trifluoromethyl-quinoline 在 吡啶硼烷 、 10% palladium on activated carbon 、 四丁基溴化铵 、 氢气 、 palladium diacetate 、 sodium carbonate 、 溶剂黄146 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 水 、 乙酸乙酯 为溶剂， 反应 39.0h， 生成 8-[(1-methyl-4-phthalimido)-butyl]-amino-6-methoxy-4-methyl-5-(3-methylphenyl)-2-trifluoromethyl-quinoline
  参考文献：
  名称：

  Antimalarial Activity of Novel 5-Aryl-8-Aminoquinoline Derivatives

  摘要：

  In an attempt to separate the antimalarial activity of tafenoquine (3) from its hemolytic side effects in glucose-6-phosphate dehydrogenase (G6PD) deficiency patients, a series of 5-aryl-8-aminoquinoline derivative, was prepared and assessed for antimalarial activities The new compounds were found metabolically stable in human and mouse microsomal preparations, with t(1/2) > 60 mm, and were equal to or more potent than primaquine (2) and 3 against Plasmodium falciparum cell growth The new agents were more active against the chloroquine (CQ) resistant clone than to the CQ-sensitive clone Analogues with electron donating groups showed better activity than those with electron withdrawing substituents Compounds 4bc, 4bd, and 4be showed comparable therapeutic index (TI) to that of 2 and 3, with TI ranging from 5 to 8 based on IC50 data The new compounds showed no significant causal prophylactic activity in mice infected with Plasmodium berghei sporozoites, but are substantially less toxic than 2 and 3 in mouse tests

  DOI：

  10.1021/jm100911f
• 作为产物：
  描述：

  5-chloro-6-methoxy-4-methyl-2-trifluoromethyl-quinoline 在 四磷十氧化物 、 potassium nitrate 作用下， 以 磷酸三乙酯 、 甲醇 为溶剂， 反应 20.0h， 以47%的产率得到5-chloro-6-methoxy-4-methyl-8-nitro-2-trifluoromethyl-quinoline
  参考文献：
  名称：

  Antimalarial Activity of Novel 5-Aryl-8-Aminoquinoline Derivatives

  摘要：

  In an attempt to separate the antimalarial activity of tafenoquine (3) from its hemolytic side effects in glucose-6-phosphate dehydrogenase (G6PD) deficiency patients, a series of 5-aryl-8-aminoquinoline derivative, was prepared and assessed for antimalarial activities The new compounds were found metabolically stable in human and mouse microsomal preparations, with t(1/2) > 60 mm, and were equal to or more potent than primaquine (2) and 3 against Plasmodium falciparum cell growth The new agents were more active against the chloroquine (CQ) resistant clone than to the CQ-sensitive clone Analogues with electron donating groups showed better activity than those with electron withdrawing substituents Compounds 4bc, 4bd, and 4be showed comparable therapeutic index (TI) to that of 2 and 3, with TI ranging from 5 to 8 based on IC50 data The new compounds showed no significant causal prophylactic activity in mice infected with Plasmodium berghei sporozoites, but are substantially less toxic than 2 and 3 in mouse tests

  DOI：

  10.1021/jm100911f

文献信息

• Antimalarial Activity of Novel 5-Aryl-8-Aminoquinoline Derivatives
  作者：Hiroaki Shiraki、Michael P. Kozar、Victor Melendez、Thomas H. Hudson、Colin Ohrt、Alan J. Magill、Ai J. Lin

  DOI：10.1021/jm100911f

  日期：2011.1.13

  In an attempt to separate the antimalarial activity of tafenoquine (3) from its hemolytic side effects in glucose-6-phosphate dehydrogenase (G6PD) deficiency patients, a series of 5-aryl-8-aminoquinoline derivative, was prepared and assessed for antimalarial activities The new compounds were found metabolically stable in human and mouse microsomal preparations, with t(1/2) > 60 mm, and were equal to or more potent than primaquine (2) and 3 against Plasmodium falciparum cell growth The new agents were more active against the chloroquine (CQ) resistant clone than to the CQ-sensitive clone Analogues with electron donating groups showed better activity than those with electron withdrawing substituents Compounds 4bc, 4bd, and 4be showed comparable therapeutic index (TI) to that of 2 and 3, with TI ranging from 5 to 8 based on IC50 data The new compounds showed no significant causal prophylactic activity in mice infected with Plasmodium berghei sporozoites, but are substantially less toxic than 2 and 3 in mouse tests