N¹,N²-bis(7-chloroquinolin-4-yl)nonane-1,9-diamine | 140926-84-7

• 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,N²-bis(7-chloroquinolin-4-yl)nonane-1,9-diamine
• 英文别名: N,N'-bis(7-chloroquinolin-4-yl)nonane-1,9-diamine
• CAS: 140926-84-7
• 化学式: C₂₇H₃₀Cl₂N₄
• 分子量: 481.468
• InChiKey: WFBBUBCIAGJIIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹,N²-bis(7-chloroquinolin-4-yl)nonane-1,9-diamine 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  [EN] ASYMMETRIC BISAMINOQUINOLINES AND BISAMINOQUINOLINES WITH VARIED LINKERS AS AUTOPHAGY INHIBITORS FOR CANCER AND OTHER THERAPY
  [FR] BISAMINOQUINOLINES ASYMÉTRIQUES ET BISAMINOQUINOLINES COMPORTANT DIVERSES SÉQUENCES DE LIAISON POUVANT ÊTRE UTILISÉES EN TANT QU'INHIBITEURS DE L'AUTOPHAGIE POUR LE TRAITEMENT DU CANCER ET D'AUTRES MALADIES

  摘要：

  这项发明提供了新型的不对称和对称双氨基喹啉和相关化合物，治疗方法和合成方法。这些新型化合物表现出有效的抗癌活性，并可用于治疗各种与自噬相关的疾病。

  公开号：

  WO2016022956A1
• 作为产物：
  描述：

  7-氯-4-羟基喹啉 在 potassium phosphate 、 palladium diacetate 、 三溴化磷 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 N¹,N²-bis(7-chloroquinolin-4-yl)nonane-1,9-diamine
  参考文献：
  名称：

  [EN] ASYMMETRIC BISAMINOQUINOLINES AND BISAMINOQUINOLINES WITH VARIED LINKERS AS AUTOPHAGY INHIBITORS FOR CANCER AND OTHER THERAPY
  [FR] BISAMINOQUINOLINES ASYMÉTRIQUES ET BISAMINOQUINOLINES COMPORTANT DIVERSES SÉQUENCES DE LIAISON POUVANT ÊTRE UTILISÉES EN TANT QU'INHIBITEURS DE L'AUTOPHAGIE POUR LE TRAITEMENT DU CANCER ET D'AUTRES MALADIES

  摘要：

  这项发明提供了新型的不对称和对称双氨基喹啉和相关化合物，治疗方法和合成方法。这些新型化合物表现出有效的抗癌活性，并可用于治疗各种与自噬相关的疾病。

  公开号：

  WO2016022956A1

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：US10221140B2

  公开（公告）日：2019-03-05

  The invention provides novel asymmetric and symmetric bisaminoquinolmes 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。
• Bisquinolines. 1. N,N-bis(7-chloroquinolin-4-yl)alkanediamines with potential against chloroquine-resistant malaria
  作者：Jonathan L. Vennerstrom、William Y. Ellis、Arba L. Ager、Steven L. Andersen、Lucia Gerena、Wilbur K. Milhous

  DOI：10.1021/jm00089a025

  日期：1992.5

  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.
• 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：EP3177595B1

  公开（公告）日：2021-02-24
• Asymmetric Bisaminoquinolines And Bisaminoquinolines With Varied Linkers As Autophagy Inhibitors For Cancer And Other Therapy
  申请人：The Trustees of the University ofPennsylvania

  公开号：US20220064118A1

  公开（公告）日：2022-03-03

  The invention provides novel asymmetric and symmetric bisaminoquinolmes 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.