N-(7-chloroquinolin-4-yl)-N-tert-butylethane-1,2-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: N-(7-chloroquinolin-4-yl)-N-tert-butylethane-1,2-diamine
• 英文别名: N'-tert-butyl-N-(7-chloroquinolin-4-yl)ethane-1,2-diamine
• 化学式: C₁₅H₂₀ClN₃
• 分子量: 277.797
• InChiKey: HZXXJVAFDVQYSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-[(7-Chloro-4-quinolinyl)amino]-N-(1,1-dimethylethyl)acetamide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以22%的产率得到N-(7-chloroquinolin-4-yl)-N-tert-butylethane-1,2-diamine
  参考文献：
  名称：

  Antimalarial Dual Drugs Based on Potent Inhibitors of Glutathione Reductase from Plasmodium falciparum

  摘要：

  Plasmodium parasites are exposed to higher fluxes of reactive oxygen species and need high activities of intracellular antioxidant systems providing a steady glutathione flux. As a future generation of dual drugs, 18 naphthoquinones and phenols (or their reduced forms) containing three different linkers between the 4-aminoquinoline core and the redox active component were synthesized. Their antimalarial effects have been characterized in parasite assays using chloroquine-sensitive and -resistant strains of Plasmodium, alone or in drug combination, and in the Plasmodium berghei rodent model. In particular, two tertiary amides 34 and 36 showed potent antimalarial activity in the low nanomolar range against CQ-resistant parasites. The ability to compete both for (Fe-III)protoporphyrin and for chloroquine transporter was determined. The data are consistent with the presence of a carrier for uptake of the short chloroquine analogue 2 but not for the potent antimalarial amide 34, suggesting a mode of action distinct from chloroquine mechanism.

  DOI：

  10.1021/jm7009292

文献信息

• Novel Short Chain Chloroquine Analogues Retain Activity Against Chloroquine Resistant K1 <i>Plasmodium falciparum</i>
  作者：Paul A. Stocks、Kaylene J. Raynes、Patrick G. Bray、B. Kevin Park、Paul. M. O'Neill、Stephen A. Ward

  DOI：10.1021/jm0108707

  日期：2002.11.1

  A series of short chain chloroquine (CQ) derivatives have been synthesized in one step from readily available starting materials. The diethylamine function of CQ is replaced by shorter alkylamine groups (4-9) containing secondary or tertiary terminal nitrogens. Some of these derivatives are significantly more potent than CQ against a CQ resistant strain of Plasmodium falciparum in vitro. We conclude that the ability to accumulate at higher concentrations within the food vacuole of the parasite is an important parameter that dictates their potency against CQ sensitive and the chloroquine resistant K1 P. falciparum.