7-benzylamino-1-isoquinolinamine | 943960-88-1

• 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: 7-benzylamino-1-isoquinolinamine
• 英文别名: N7-benzylisoquinoline-1,7-diamine；7-N-benzylisoquinoline-1,7-diamine
• CAS: 943960-88-1
• 化学式: C₁₆H₁₅N₃
• 分子量: 249.315
• InChiKey: JXQBBIFWKOFRNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-benzylamino-1-isoquinolinamine 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 7-N-benzylisoquinoline-1,7-diamine;hydrochloride
  参考文献：
  名称：

  In vitro efficacy of 7-benzylamino-1-isoquinolinamines against Plasmodium falciparum related to the efficacy of chalcones

  摘要：

  A series of 1,7-diaminoisoquinolinamines, that are expected to mediate antimalarial activity by the same mechanism employed by the chalcones, were produced. Six 7-benzylamino-1-isoquinolinamines were found to be submicromolar inhibitors in vitro of drug-resistant Plasmodium falciparum, with the best possessing activity comparable to chloroquine. Despite being developed from a lead that is a DHFR inhibitor, these compounds do not mediate their antimalarial effects by inhibition of DHFR. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.099
• 作为产物：
  描述：

  在 10% palladium on activated charcoal 、 氢气 、 sodium cyanoborohydride 作用下， 生成 7-benzylamino-1-isoquinolinamine
  参考文献：
  名称：

  In vitro efficacy of 7-benzylamino-1-isoquinolinamines against Plasmodium falciparum related to the efficacy of chalcones

  摘要：

  A series of 1,7-diaminoisoquinolinamines, that are expected to mediate antimalarial activity by the same mechanism employed by the chalcones, were produced. Six 7-benzylamino-1-isoquinolinamines were found to be submicromolar inhibitors in vitro of drug-resistant Plasmodium falciparum, with the best possessing activity comparable to chloroquine. Despite being developed from a lead that is a DHFR inhibitor, these compounds do not mediate their antimalarial effects by inhibition of DHFR. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.11.099

文献信息

• Synthesis and antimalarial activity of 7-benzylamino-1-isoquinolinamines
  作者：Clare E. Gutteridge、Marshall M. Hoffman、Apurba K. Bhattacharjee、Lucia Gerena

  DOI：10.1002/jhet.5570440319

  日期：2007.5

  suggests that 7-benzylamino-1-isoquinolinamines should mediate antimalarial effects by a mechanism distinct from that employed by existing antimalarial drugs. A series of these compounds was prepared in seven synthetic steps, via reductive amination of 1,7-isoquinolinediamine. In vitro efficacy testing of the novel compounds against Plasmodium falciparum revealed them to be potent antimalarial agents.

  计算机模型表明7-苄基氨基-1-异喹啉胺应通过不同于现有抗疟药所采用的机制来介导抗疟作用。通过1,7-异喹啉二胺的还原胺化反应，在七个合成步骤中制备了一系列这些化合物。新型化合物对恶性疟原虫的体外功效测试表明，它们是有效的抗疟药。
• In vitro efficacy of 7-benzylamino-1-isoquinolinamines against Plasmodium falciparum related to the efficacy of chalcones
  作者：Clare E. Gutteridge、Marshall M. Hoffman、Apurba K. Bhattacharjee、Wilbur K. Milhous、Lucia Gerena

  DOI：10.1016/j.bmcl.2010.11.099

  日期：2011.1

  A series of 1,7-diaminoisoquinolinamines, that are expected to mediate antimalarial activity by the same mechanism employed by the chalcones, were produced. Six 7-benzylamino-1-isoquinolinamines were found to be submicromolar inhibitors in vitro of drug-resistant Plasmodium falciparum, with the best possessing activity comparable to chloroquine. Despite being developed from a lead that is a DHFR inhibitor, these compounds do not mediate their antimalarial effects by inhibition of DHFR. Published by Elsevier Ltd.