N,N'-双(7-氯-4-喹啉)-1,2-乙二胺 | 140926-75-6

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 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
• 中文名称: N,N'-双(7-氯-4-喹啉)-1,2-乙二胺
• 英文名称: N1,N2-bis(7-chloroquinolin-4-yl)ethane-1,2-diamine
• 英文别名: N,N'-bis(7-chloroquinolin-4-yl)ethane-1,2-diamine
• CAS: 140926-75-6
• 化学式: C₂₀H₁₆Cl₂N₄
• 分子量: 383.28
• InChiKey: SSXYXSMMVMVYEV-UHFFFAOYSA-N

物化性质

• 沸点：
  632.6±55.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：0.33mg/mL； DMSO：0.25mg/mL；乙醇：微溶

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

生物活性

NSC5844 是一种 4-氨基喹啉衍生物，具有抗肿瘤和抗疟疾活性。

靶点

寄生虫

体外研究

NSC5844（化合物10）是一种 4-氨基喹啉衍生物，并表现出抗肿瘤活性，其对 MDA-MB-468 和 MCF-7 细胞的半数抑制浓度 (GI₅₀) 分别为 7.35 ± 0.10 μM 和 14.80 ± 0.35 μM。此外，NSC5844（化合物1）对恶性疟原虫具有细胞毒性，并能抑制氯喹敏感型 (D-6) 和耐药型 (W-2) 恶性疟原虫克隆的生长，其半数抑制浓度 (IC₅₀) 分别为 17 nM 和 27 nM。

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 、 乙二胺 在 三乙胺 作用下， 以 various solvent(s) 为溶剂， 以85%的产率得到N,N'-双(7-氯-4-喹啉)-1,2-乙二胺
  参考文献：
  名称：

  Bisquinolines. 1. N,N-bis(7-chloroquinolin-4-yl)alkanediamines with potential against chloroquine-resistant malaria

  摘要：

  On the basis of observations that several bisquinolines such as piperaquine possess notable activity against chloroquine-resistant malaria, 13 N,N-bis-(7-chloroquinolin-4-yl)alkanediamines were synthesized and screened against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Twelve of the thirteen bisquinolines had a significantly lower resistance index than did chloroquine; the resistance index was apparently unrelated to either in vitro or in vivo activity. Except for two compounds, there was a reasonable correlation between in vitro and in vivo activities. Seven of the thirteen bisquinolines had IC50's of less than 6 nM against both chloroquine-sensitive (D-6) and -resistant (W-2) clones of P. falciparum and were curative against P. berghei at doses of 640 mg/kg. In contrast to chloroquine, these bisquinolines did not show any toxic deaths at curative dose levels. Four bisquinolines, however, caused skin lesions at the site of injection. Maximum activity was seen in bisquinolines with a connecting bridge of two carbon atoms where decreased conformational mobility seemed to increase activity. Bisquinoline 3 ((+/-)-trans-N1,N2-bis(7-chloroquinolin-4-yl)cyclohexane-1,2-diamine was not only the most potent bisquinoline in vitro, but was clearly unique in its in vivo activity-80% and 100% cure rates were achieved at doses of 160 and 320 mg/kg, respectively. In summary, these preliminary results support the premise that bisquinolines may be useful agents against chloroquine-resistant malaria.

  DOI：

  10.1021/jm00089a025

文献信息

• ASYMMETRIC BISAMINOQUINOLINES AND BISAMINOQUINOLINES WITH VARIED LINKERS AS AUTOPHAGY INHIBITORS FOR CANCER AND OTHER THERAPY
  申请人：The Trustees of The University of Pennsylvania

  公开号：EP3848355A1

  公开（公告）日：2021-07-14

  The invention provides novel asymmetric and symmetric bisaminoquinolines and related compounds, methods of treatment and syntheses. The novel compounds exhibit effective anticancer activity and are useful in the treatment of a variety of autophagy-related disorders.

  本发明提供了新型不对称和对称双氨基喹啉及相关化合物、治疗方法和合成方法。这些新型化合物具有有效的抗癌活性，可用于治疗多种自噬相关疾病。
• Pearson; Jones; Cope, Journal of the American Chemical Society, 1946, vol. 68, p. 1227
  作者：Pearson、Jones、Cope

  DOI：——

  日期：——
• ANTIANGIOGENIC SMALL MOLECULES AND METHODS OF USE
  申请人：Zudaire Enrique

  公开号：US20120129775A1

  公开（公告）日：2012-05-24

  Methods of inhibiting undesired angiogenesis are provided, which methods include administering to a subject a therapeutically effective amount of at least one of the compounds described herein, or a pharmaceutically acceptable salt thereof.
• US9186365B2
  申请人：——

  公开号：US9186365B2

  公开（公告）日：2015-11-17
• US9504729B2
  申请人：——

  公开号：US9504729B2

  公开（公告）日：2016-11-29