N¹-(6-methoxy-[8]quinolyl)-1-methyl-propanediyldiamine | 34332-51-9

• 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-(6-methoxy-[8]quinolyl)-1-methyl-propanediyldiamine
• 英文别名: N¹-(6-Methoxy-[8]chinolyl)-1-methyl-propandiyldiamin；3-N-(6-methoxyquinolin-8-yl)butane-1,3-diamine
• CAS: 34332-51-9
• 化学式: C₁₄H₁₉N₃O
• 分子量: 245.324
• InChiKey: ZBNVUTPGZIDATC-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C(Solv: ethanol (64-17-5))
• 沸点：
  436.8±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹-(6-methoxy-[8]quinolyl)-1-methyl-propanediyldiamine 、 方酸二正丁酯 以 甲醇 为溶剂， 反应 24.0h， 以21%的产率得到3-butoxy-4-({3-[(6-methoxyquinolin-8-yl)amino]butyl}amino)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Novel squaramides with in vitro liver stage antiplasmodial activity

  摘要：

  A structure-activity relationship study was performed with ten 8-aminoquinoline-squaramides compounds active against liver stage malaria parasites, using human hepatoma cells (Huh7) infected by Plasmodium berghei parasites. In addition, their blood-schizontocidal activity was assessed against chloroquine-resistant W2 strain Plasmodium falciparum. Compound 3 was 7.3-fold more potent than the positive control primaquine against liver-stage parasites, illustrating the importance of the squarate moiety to activity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.005
• 作为产物：
  描述：

  8-氨基-6-甲氧基喹啉 在 一水合肼 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 39.0h， 生成 N¹-(6-methoxy-[8]quinolyl)-1-methyl-propanediyldiamine
  参考文献：
  名称：

  Novel squaramides with in vitro liver stage antiplasmodial activity

  摘要：

  A structure-activity relationship study was performed with ten 8-aminoquinoline-squaramides compounds active against liver stage malaria parasites, using human hepatoma cells (Huh7) infected by Plasmodium berghei parasites. In addition, their blood-schizontocidal activity was assessed against chloroquine-resistant W2 strain Plasmodium falciparum. Compound 3 was 7.3-fold more potent than the positive control primaquine against liver-stage parasites, illustrating the importance of the squarate moiety to activity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.005

文献信息

• Further Syntheses of Primaquine Analogs¹
  作者：Robert C. Elderfield、Elizabeth F. Claflin、Holly E. Mertel、Orville L. McCurdy、Richard T. Mitch、Charles D. Ver Nooy、Bruce H. Wark、Iris M. Wempen

  DOI：10.1021/ja01623a039

  日期：1955.9
• Kimura, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, p. 325,328
  作者：Kimura

  DOI：——

  日期：——
• Process for the preparation and manufacture of 6-methoxy-8-(4-amino-1-methylbutylamino)-quinoline
  申请人：ELDERFIELD ROBERT C

  公开号：US02604474A1

  公开（公告）日：1952-07-22
• Novel squaramides with in vitro liver stage antiplasmodial activity
  作者：Carlos J.A. Ribeiro、Margarida Espadinha、Marta Machado、Jiri Gut、Lídia M. Gonçalves、Philip J. Rosenthal、Miguel Prudêncio、Rui Moreira、Maria M.M. Santos

  DOI：10.1016/j.bmc.2016.03.005

  日期：2016.4

  A structure-activity relationship study was performed with ten 8-aminoquinoline-squaramides compounds active against liver stage malaria parasites, using human hepatoma cells (Huh7) infected by Plasmodium berghei parasites. In addition, their blood-schizontocidal activity was assessed against chloroquine-resistant W2 strain Plasmodium falciparum. Compound 3 was 7.3-fold more potent than the positive control primaquine against liver-stage parasites, illustrating the importance of the squarate moiety to activity. (C) 2016 Elsevier Ltd. All rights reserved.