(S)-2-(7-chloroquinolin-4-ylamino)-1-(4-phenylpiperazin-1-yl)propan-1-one | 1616683-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-2-(7-chloroquinolin-4-ylamino)-1-(4-phenylpiperazin-1-yl)propan-1-one
• 英文别名: (2S)-2-[(7-chloroquinolin-4-yl)amino]-1-(4-phenylpiperazin-1-yl)propan-1-one
• CAS: 1616683-91-0
• 化学式: C₂₂H₂₃ClN₄O
• 分子量: 394.904
• InChiKey: PRFZUYXTOLKJGE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 苯酚 为溶剂， 反应 5.0h， 生成 (S)-2-(7-chloroquinolin-4-ylamino)-1-(4-phenylpiperazin-1-yl)propan-1-one
  参考文献：
  名称：

  Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain

  摘要：

  Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β(3)- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI=5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.

  DOI：

  10.1016/j.bmc.2014.05.024

文献信息

• Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain
  作者：Manish Sinha、Vasanth R. Dola、Pooja Agarwal、Kumkum Srivastava、Wahajul Haq、Sunil K. Puri、Seturam B. Katti

  DOI：10.1016/j.bmc.2014.05.024

  日期：2014.7

  Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β(3)- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI=5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.