N1-benzylidene-N4-(7-chloroquinolin-4-yl) butane-1,4-diamine | 244609-02-7

• 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: N1-benzylidene-N4-(7-chloroquinolin-4-yl) butane-1,4-diamine
• 英文别名: N-[4-(benzylideneamino)butyl]-7-chloroquinolin-4-amine
• CAS: 244609-02-7
• 化学式: C₂₀H₂₀ClN₃
• 分子量: 337.852
• InChiKey: RIZOFCFQSDJSSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N1-benzylidene-N4-(7-chloroquinolin-4-yl) butane-1,4-diamine 在 盐酸 、 叠氮基三甲基硅烷 、 水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 7-chloro-N-{4-[phenyl(1H-tetrazol-5-yl)methylamino]butyl}quinolin-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
• 作为产物：
  描述：

  4-(4-氨基丁基)氨基-7-氯喹啉 、 苯甲醛 以 甲醇 为溶剂， 反应 0.08h， 生成 N1-benzylidene-N4-(7-chloroquinolin-4-yl) butane-1,4-diamine
  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.