3-bromo-chloroquine | 32571-41-8

• 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: 3-bromo-chloroquine
• 英文别名: N⁴,N⁴-diethyl-N¹-(3-bromo-7-chloro-[4]quinolyl)-1-methyl-butanediyldiamine；N⁴,N⁴-Diaethyl-N¹-(3-brom-7-chlor-[4]chinolyl)-1-methyl-butandiyldiamin；4-N-(3-bromo-7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
• CAS: 32571-41-8
• 化学式: C₁₈H₂₅BrClN₃
• 分子量: 398.774
• InChiKey: BDXOOOHCAOBWTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 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：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-chloroquine 在 copper(l) iodide 、 sodium azide 、 sodium ascorbate 、 三乙胺 、 N,N'-二甲基乙二胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 N‐(7‐chloro‐4‐{[5‐(diethylamino)pentan‐2‐yl]amino}quinolin‐3‐yl)‐4-(methylsulfanyl)benzamide
  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
• 作为产物：
  描述：

  Ethyl-7-chlor-4-hydroxy-2-chinolincarboxylat 在 sodium hydroxide 、 二苯醚 、 联苯 、 溴 、 碘 、 溶剂黄146 、 三氯氧磷 作用下， 生成 3-bromo-chloroquine
  参考文献：
  名称：

  The Preparation of 3-Halo-4-dialkylaminoalkylaminoquinoline Derivatives

  摘要：

  DOI：

  10.1021/ja01216a044

文献信息

• The Preparation of 3-Halo-4-dialkylaminoalkylaminoquinoline Derivatives
  作者：Alexander R. Surrey、Royal A. Cutler

  DOI：10.1021/ja01216a044

  日期：1946.12
• 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.