1-(2-Bromo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline

• 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-(2-Bromo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 1-(2-Bromophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: AXOQZSCPPBRDTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 4.0h， 生成 1-(2-Bromo-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro

  摘要：

  A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1(IIIB) in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 mu M respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 mu M, which resulted in SI values larger than 95, 159, and 130 respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.040

文献信息

• One-step preparation of 1-substituted tetrahydroisoquinolines via the Pictet–Spengler reaction using zeolite catalysts
  作者：Adrienn Hegedüs、Zoltán Hell

  DOI：10.1016/j.tetlet.2004.09.097

  日期：2004.11

  A new, environmentally friendly variation of the Pictet-Spengler reaction has been elaborated using a small pore size zeolite. The easily separable and recyclable catalyst provided high conversions and a shorter reaction time than the classical acetic acid or trifluoroacetic acid. (C) 2004 Elsevier Ltd. All rights reserved.
• US4001244A
  申请人：——

  公开号：US4001244A

  公开（公告）日：1977-01-04