6,7-dihydroxy-1-isobutyl-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: 6,7-dihydroxy-1-isobutyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(2-Methylpropyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol；1-(2-methylpropyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: JTQIDIWFNQOTSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 水 、 氢溴酸 、 连二磷酸 作用下， 生成 6,7-dihydroxy-1-isobutyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Tetrahydroisoquinolines. I. 1-Alkyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines¹

  摘要：

  DOI：

  10.1021/ja01125a051

文献信息

• Synthesis, Purification, and Selective β₂-AR Agonist and Bronchodilatory Effects of Catecholic Tetrahydroisoquinolines from <i>Portulaca oleracea</i>
  作者：Er-Lan Yang、Bin Sun、Zi-Yi Huang、Jian-Guang Lin、Bo Jiao、Lan Xiang

  DOI：10.1021/acs.jnatprod.9b00418

  日期：2019.11.22

  A green, biomimetic, phosphate-mediated Pictet-Spengler reaction was used in the synthesis of three catecholic tetrahydroisoquinolines, 1, 2, and 12, present in the medicinal plant Portulaca oleracea, as well as their analogues 3-11, 13, and 14, with dopamine hydrochloride and aldehydes as the substrates. AB-8 macroporous resin column chromatography was applied for purification of the products from the one-step high efficacy synthesis. It eliminated the difficulties in the isolation of catecholic tetrahydroisoquinolines from the aqueous reaction system and unreacted dopamine hydrochloride. Activity screening in CHO-K1/G alpha 15 cell models consistently expressing alpha(1B)-, beta(1)-, or beta(2)-adrenergic receptors indicated that 12 and 2, compounds that are present in P. oleracea, possessed the most potent beta(2)-adrenergic receptor agonist activity and 2 was a selective beta(2)-adrenergic receptor agonist at the concentration of 100 mu M. Both 12 and 2 exhibited dose-dependent bronchodilator effects on the histamine-induced contraction of isolated guinea-pig tracheal smooth muscle, with EC50 values of 0.8 and 2.8 mu M, respectively. These findings explain the scientific rationale of P. oleracea use as an antiasthmatic herb in folk medicine and provide the basis for the discovery of novel antiasthma drugs.
• 1-alkyl-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline compounds
  申请人：SMITH KLINE FRENCH LAB

  公开号：US02663709A1

  公开（公告）日：1953-12-22
• Tetrahydroisoquinolines. I. 1-Alkyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolines¹
  作者：P. N. Craig、F. P. Nabenhauer、P. M. Williams、E. Macko、J. Toner

  DOI：10.1021/ja01125a051

  日期：1952.3