N-{2-[(1H-tetrazol-5-yl)(p-tolyl)methylamino]ethyl}-7-chloroquinolin-4-amine

• 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-{2-[(1H-tetrazol-5-yl)(p-tolyl)methylamino]ethyl}-7-chloroquinolin-4-amine
• 英文别名: N-(7-chloroquinolin-4-yl)-N'-[(4-methylphenyl)-(2H-tetrazol-5-yl)methyl]ethane-1,2-diamine
• 化学式: C₂₀H₂₀ClN₇
• 分子量: 393.879
• InChiKey: AAUCGIDHMKCVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2-氨基乙基)氨基-7-氯喹啉 在 盐酸 、 叠氮基三甲基硅烷 、 水 作用下， 以 甲醇 为溶剂， 反应 24.08h， 生成 N-{2-[(1H-tetrazol-5-yl)(p-tolyl)methylamino]ethyl}-7-chloroquinolin-4-amine
  参考文献：
  名称：

  Synthesis and in Vitro and in Vivo Pharmacological Evaluation of New 4-Aminoquinoline-Based Compounds

  摘要：

  A new class of 4-aminoquinolines was synthesized and evaluated in vitro for antiplasmodial activity against both, the chloroquine-sensitive (3D7) and -resistant (K1 and W2) strains. The most active compounds 3c-3e had acceptable cytotoxicity but showed strong inhibition toward a panel of cytochrome P450 enzymes in vitro. Pharmacokinetic studies on 3d and 3e in mice showed that they had moderate half-life (4-6 h) and low oral bioavailability. The front runner compound 3d exhibited moderate inhibition of the malaria parasite on P. berghei infected mice following oral administration (5 mg/kg), achieving reduction of parasitemia population by 47% on day 7.

  DOI：

  10.1021/ml400311r

文献信息

• Synthesis and in Vitro and in Vivo Pharmacological Evaluation of New 4-Aminoquinoline-Based Compounds
  作者：Matshawandile Tukulula、Mathew Njoroge、Efrem T. Abay、Grace C. Mugumbate、Lubbe Wiesner、Dale Taylor、Liezl Gibhard、Jennifer Norman、Kenneth J. Swart、Jiri Gut、Philip J. Rosenthal、Samuel Barteau、Judith Streckfuss、Jacques Kameni-Tcheudji、Kelly Chibale

  DOI：10.1021/ml400311r

  日期：2013.12.12

  A new class of 4-aminoquinolines was synthesized and evaluated in vitro for antiplasmodial activity against both, the chloroquine-sensitive (3D7) and -resistant (K1 and W2) strains. The most active compounds 3c-3e had acceptable cytotoxicity but showed strong inhibition toward a panel of cytochrome P450 enzymes in vitro. Pharmacokinetic studies on 3d and 3e in mice showed that they had moderate half-life (4-6 h) and low oral bioavailability. The front runner compound 3d exhibited moderate inhibition of the malaria parasite on P. berghei infected mice following oral administration (5 mg/kg), achieving reduction of parasitemia population by 47% on day 7.