N⁴-(7-chloro-3-nitroquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine

• 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: N⁴-(7-chloro-3-nitroquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine
• 英文别名: 4-N-(7-chloro-3-nitroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
• 化学式: C₁₈H₂₅ClN₄O₂
• 分子量: 364.875
• InChiKey: VUUJVASZOJJHEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-(7-chloro-3-nitroquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine 在 乙醇 、 tin(ll) chloride 作用下， 反应 2.0h， 以60%的产率得到7-chloro-N⁴-[4-(diethylamino)-1-methylbutyl]quinoline-3,4-diamine
  参考文献：
  名称：

  Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice

  摘要：

  In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50 < 1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50 < 1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.

  DOI：

  10.1021/acsmedchemlett.8b00053
• 作为产物：
  描述：

  7-氯-4-羟基-3-硝基喹啉 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 18.5h， 生成 N⁴-(7-chloro-3-nitroquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine
  参考文献：
  名称：

  Synthesis and antimalarial activity of novel 3-substituted chloroquine derivatives

  摘要：

  The synthesis and characterization of a series of new 3-substituted chloroquine (CQ) derivatives are reported along with their antimalarial activity against CQ-sensitive, 3D7, and CQ-resistant, Dd2, strains of Plasmodium falciparum. The new CQ derivatives stem from the aroylation of 3-aminochloroquine, which in turn is prepared in four efficient steps from 4,7-dichloroquinoline. Variation of the aroylation substituents and ring substitution patterns reveal that 4-substitution with electron-withdrawing moieties results in the lowest IC₅₀ values, both in the same order of magnitude as CQ itself for the 3D7 strain. Given its activity against the resistant Dd2 strain, the 4-chlorobenzamido-CQ derivative is chosen as the lead compound for potential use in combination therapy.

  DOI：

  10.1139/cjc-2023-0062

文献信息

• Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in <i>Leishmania infantum</i> Infected Mice
  作者：Jelena Konstantinović、Milica Videnović、Stefania Orsini、Katarina Bogojević、Sarah D’Alessandro、Diletta Scaccabarozzi、Nataša Terzić Jovanović、Luigi Gradoni、Nicoletta Basilico、Bogdan A. Šolaja

  DOI：10.1021/acsmedchemlett.8b00053

  日期：2018.7.12

  In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50 < 1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50 < 1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.
• Synthesis and antimalarial activity of novel 3-substituted chloroquine derivatives
  作者：Benita Kapuku、Fadi Baakdah、Elias Georges、D. Scott Bohle

  DOI：10.1139/cjc-2023-0062

  日期：2024.2.1

  The synthesis and characterization of a series of new 3-substituted chloroquine (CQ) derivatives are reported along with their antimalarial activity against CQ-sensitive, 3D7, and CQ-resistant, Dd2, strains of Plasmodium falciparum. The new CQ derivatives stem from the aroylation of 3-aminochloroquine, which in turn is prepared in four efficient steps from 4,7-dichloroquinoline. Variation of the aroylation substituents and ring substitution patterns reveal that 4-substitution with electron-withdrawing moieties results in the lowest IC₅₀ values, both in the same order of magnitude as CQ itself for the 3D7 strain. Given its activity against the resistant Dd2 strain, the 4-chlorobenzamido-CQ derivative is chosen as the lead compound for potential use in combination therapy.