8-[(1-methyl-4-phthalimido)-butyl]-amino-2,6-dimethoxy-4-methyl-5-(3,4-dichlorophenyl)-quinoline | 1260253-90-4

• 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: 8-[(1-methyl-4-phthalimido)-butyl]-amino-2,6-dimethoxy-4-methyl-5-(3,4-dichlorophenyl)-quinoline
• 英文别名: 2-[4-[[5-(3,4-Dichlorophenyl)-2,6-dimethoxy-4-methylquinolin-8-yl]amino]pentyl]isoindole-1,3-dione
• CAS: 1260253-90-4
• 化学式: C₃₁H₂₉Cl₂N₃O₄
• 分子量: 578.495
• InChiKey: ACRYICGUAGMAEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁二酸 、 8-[(1-methyl-4-phthalimido)-butyl]-amino-2,6-dimethoxy-4-methyl-5-(3,4-dichlorophenyl)-quinoline 在 一水合肼 作用下， 以 乙醇 、 甲醇 、 乙腈 为溶剂， 以37%的产率得到8-[(4-amino-1-methyl)-butyl]-amino-5-(3,4-dichlorophenyl)-2,6-dimethoxy-4-methyl-quinoline succinate
  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：

  2-氯-6-甲氧基-4-甲基-喹啉 在 磺酰氯 、 四磷十氧化物 、 四丁基溴化铵 、 氢气 、 palladium diacetate 、 sodium carbonate 、 二异丙胺 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 乙二醇二甲醚 、 磷酸三乙酯 、 水 、 溶剂黄146 为溶剂， 20.0~80.0 ℃ 、344.75 kPa 条件下， 反应 44.75h， 生成 8-[(1-methyl-4-phthalimido)-butyl]-amino-2,6-dimethoxy-4-methyl-5-(3,4-dichlorophenyl)-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