N-(7-chloroquinolin-4-yl)-N'-methyl-N'-[3-(quinolin-2-ylamino)propyl]propane-1,3-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'-methyl-N'-[3-(quinolin-2-ylamino)propyl]propane-1,3-diamine
• 化学式: C₂₅H₂₈ClN₅
• 分子量: 433.984
• InChiKey: MTPIAGPSTYVUFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-双(3-氨丙基)甲胺 在 碳酸氢钠 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 生成 N-(7-chloroquinolin-4-yl)-N'-methyl-N'-[3-(quinolin-2-ylamino)propyl]propane-1,3-diamine
  参考文献：
  名称：

  Potent Antimalarial Activity of Two Arenes Linked with Triamine Designed To Have Multiple Interactions with Heme

  摘要：

  Based on the idea that compounds designed to exhibit high affinity for heme would block hemozoin formation, a critical heme-detoxification process for malarial parasites, we synthesized a series of compounds with two pi-conjugated moieties at terminal amino groups of triamine. These compounds exhibited moderate to high antimalarial activities in vitro toward both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum. In a P. berghei-infected mouse model, 3a and 12a showed potent antimalarial activities compared to artesunate, as well as a prolonged duration of antimalarial effect. We found a good correlation between protective activity against hemin degradation and antimalarial activity. Compounds 8b and 3a strongly inhibited hemozoin formation catalyzed by heme detoxification protein.

  DOI：

  10.1021/acsmedchemlett.8b00222

文献信息

• Potent Antimalarial Activity of Two Arenes Linked with Triamine Designed To Have Multiple Interactions with Heme
  作者：Yosuke Sakata、Kosuke Yabunaka、Yuko Kobayashi、Hirohisa Omiya、Naoki Umezawa、Hye-Sook Kim、Yusuke Wataya、Yoshimi Tomita、Yosuke Hisamatsu、Nobuki Kato、Hirokazu Yagi、Tadashi Satoh、Koichi Kato、Haruto Ishikawa、Tsunehiko Higuchi

  DOI：10.1021/acsmedchemlett.8b00222

  日期：2018.10.11

  Based on the idea that compounds designed to exhibit high affinity for heme would block hemozoin formation, a critical heme-detoxification process for malarial parasites, we synthesized a series of compounds with two pi-conjugated moieties at terminal amino groups of triamine. These compounds exhibited moderate to high antimalarial activities in vitro toward both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum. In a P. berghei-infected mouse model, 3a and 12a showed potent antimalarial activities compared to artesunate, as well as a prolonged duration of antimalarial effect. We found a good correlation between protective activity against hemin degradation and antimalarial activity. Compounds 8b and 3a strongly inhibited hemozoin formation catalyzed by heme detoxification protein.