1-n-pentyl-2-propargyl-1,2,3,4-tetrahydroisoquinoline | 1189162-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-n-pentyl-2-propargyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-pentyl-2-prop-2-ynyl-3,4-dihydro-1H-isoquinoline
• CAS: 1189162-67-1
• 化学式: C₁₇H₂₃N
• 分子量: 241.376
• InChiKey: ZOVHNCXLVUXWRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-pentyl-1,2,3,4-tetrahydroisoquinoline 、 3-溴丙炔 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以85%的产率得到1-n-pentyl-2-propargyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells

  摘要：

  The synthesis of several 1-alkyl-1,2,3,4-tetrahydroisoquinolines, which may play an important role in Parkinson's disease, has been achieved by modified Pictet-Spengler cyclization of the formyliminium ion. The direct cytotoxicity and preventative effects towards MPP+-mediated death of PC12 cells were estimated. The cytotoxicities of 1-alkyl-TIQs were apoptotic and depended on their lipophilic properties. Conversely, introducing the N-propargyl substituent reduced cytotoxicity. 1-Methyl-, 1-methyl-N-propargyl- and 1-cyclopropyl-TIQ partially inhibited MPP+-induced cell death, whereas relatively large alkyl substituents at the first position did not enhance the viability of PC12 cells. In summary, our findings suggest a crucial role for the N-propargyl functional group for the effective reduction of cytotoxicity, and show the importance of size and lipophilicity of substituents at the 1-position of 1-alkyl TIQs. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.035

文献信息

• Facile synthesis and in vitro properties of 1-alkyl- and 1-alkyl-N-propargyl-1,2,3,4-tetrahydroisoquinoline derivatives on PC12 cells
  作者：Michikazu Kitabatake、Junko Nagai、Kenji Abe、Yukihiro Tsuchiya、Keita Ogawa、Takashi Yokoyama、Kunihiko Mohri、Kyoji Taguchi、Yoshie Horiguchi

  DOI：10.1016/j.ejmech.2009.04.035

  日期：2009.10

  The synthesis of several 1-alkyl-1,2,3,4-tetrahydroisoquinolines, which may play an important role in Parkinson's disease, has been achieved by modified Pictet-Spengler cyclization of the formyliminium ion. The direct cytotoxicity and preventative effects towards MPP+-mediated death of PC12 cells were estimated. The cytotoxicities of 1-alkyl-TIQs were apoptotic and depended on their lipophilic properties. Conversely, introducing the N-propargyl substituent reduced cytotoxicity. 1-Methyl-, 1-methyl-N-propargyl- and 1-cyclopropyl-TIQ partially inhibited MPP+-induced cell death, whereas relatively large alkyl substituents at the first position did not enhance the viability of PC12 cells. In summary, our findings suggest a crucial role for the N-propargyl functional group for the effective reduction of cytotoxicity, and show the importance of size and lipophilicity of substituents at the 1-position of 1-alkyl TIQs. (C) 2009 Elsevier Masson SAS. All rights reserved.