N-butyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

• 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: N-butyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-butyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline；2-Butyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isochinolin；2-butyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: ODQYFKGATDNAAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.6
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 在 硫酸 、 水 、 锌 、 苯 作用下， 生成 N-butyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  2-Alkyl-1,2,3,4-tetrahydroisoquinoline Hydrochlorides¹

  摘要：

  DOI：

  10.1021/ja01276a023

文献信息

• Multifunctional thiosemicarbazones and deconstructed analogues as a strategy to study the involvement of metal chelation, Sigma-2 (σ2) receptor and P-gp protein in the cytotoxic action: In vitro and in vivo activity in pancreatic tumors
  作者：Maria Laura Pati、Mauro Niso、Dirk Spitzer、Francesco Berardi、Marialessandra Contino、Chiara Riganti、William G. Hawkins、Carmen Abate

  DOI：10.1016/j.ejmech.2017.12.024

  日期：2018.1

  The aggressiveness of pancreatic cancer urgently requires more efficient treatment options. Because the sigma-2 (sigma(2)) receptor was recently proposed as a promising target for pancreatic cancer therapy, we explored our previously developed multifunctional thiosemicarbazones, designed to synergistically impair cell energy levels, by targeting sigma(2) and P-gp proteins and chelating Iron. A deconstruction approach was herein applied by removing one function at a time from the potent multifunctional thiosemicarbazones 1 and 2, to investigate the contribution to cytotoxicity of each target involved. The results from in vitro (panel of pancreatic tumor cells) and in vivo experiments (C57BL/6 bearing KP02 tumor), suggest that while the multifunctional activity was not required for the antitumor activity of these thiosemicarbazones, sigma(2)-targeting appeared to allow alternative tumor cell death mechanisms, leading to potent and less toxic off-targets toxicities compared to other thiosemicarbazones devoid of sigma(2)-targeting. (C) 2017 Elsevier Masson SAS. All rights reserved.
• 2-Alkyl-1,2,3,4-tetrahydroisoquinoline Hydrochlorides¹
  作者：Johannes S. Buck、Walter S. Ide

  DOI：10.1021/ja01276a023

  日期：1938.9