1-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol

• 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-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol
• 英文别名: 1-(4-Methylphenyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline；1-(4-Methylphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: FLADCOBOTUAXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol 、 2-(3,4-二羟基苯基)乙胺 氢溴酸盐 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以35%的产率得到6,7-dihydroxy-1[4-(6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-1-yl)phenyl]-1,2,3,4-tetrahydroisoquinoline dihydrobromide
  参考文献：
  名称：

  异喹啉生物碱合成中的区域选择性

  摘要：

  在此分析异喹啉生物碱合成中的区域选择性。我们的实验表明，起始胺的芳环上的取代基是异喹啉合成中的决定性基团。首次提出了二环己基碳二亚胺在活化羧酸以进行亲电芳族取代反应中的用途。

  DOI：

  10.1016/j.tetlet.2010.01.115
• 作为产物：
  描述：

  盐酸多巴胺 、 对甲基苯甲醛 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以77%的产率得到1-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol
  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

• 1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
  作者：Pi Cheng、Ning Huang、Zhi-Yong Jiang、Quan Zhang、Yong-Tang Zheng、Ji-Jun Chen、Xue-Mei Zhang、Yun-Bao Ma

  DOI：10.1016/j.bmcl.2008.02.040

  日期：2008.4

  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.
• Regioselectivity in isoquinoline alkaloid synthesis
  作者：Rodolfo Quevedo、Edwin Baquero、Mario Rodriguez

  DOI：10.1016/j.tetlet.2010.01.115

  日期：2010.3

  Regioselectivity in isoquinoline alkaloid synthesis is analyzed here. Our experiments have shown that substituents on the aromatic ring of the starting amine are determinant in isoquinoline synthesis. The use of dicyclohexylcarbodiimide in activating carboxylic acids for electrophilic aromatic substitution reactions is presented for the first time.

  在此分析异喹啉生物碱合成中的区域选择性。我们的实验表明，起始胺的芳环上的取代基是异喹啉合成中的决定性基团。首次提出了二环己基碳二亚胺在活化羧酸以进行亲电芳族取代反应中的用途。