6,7-dihydroxy-1-(3,4-dihydroxyphenyl)-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-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(3,4-Dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol；1-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: BGTFAVHCDMORNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  盐酸多巴胺 、 3,4-二羟基苯甲醛 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 维生素 C 作用下， 以 水 为溶剂， 反应 6.0h， 以67%的产率得到6,7-dihydroxy-1-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis, Purification, and Selective β₂-AR Agonist and Bronchodilatory Effects of Catecholic Tetrahydroisoquinolines from Portulaca oleracea

  摘要：

  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.

  DOI：

  10.1021/acs.jnatprod.9b00418

文献信息

• ANTI-ANGIOGENIC COMPOUNDS
  申请人：University College Dublin National University of Ireland, Dublin

  公开号：US20150218100A1

  公开（公告）日：2015-08-06

  (E)-2-(2-Quinolin-2-yl-propenyl)-phenol, 2-Quinolin-2-yl-ylethynyl-phenol and salts thereof are useful as medicaments, especially for treatment of an angiogenesis-related disease or disorder.

  (E)-2-(2-喹啉基丙烯基)-苯酚、2-喹啉-2-基乙炔基-苯酚及其盐类可用作药物，特别是用于治疗与血管生成相关的疾病或障碍。
• ANTI-ANGIOGENIC COMPOUND
  申请人：University College Dublin, National University of Ireland, Dublin

  公开号：EP3147280A1

  公开（公告）日：2017-03-29

  A compound of the formula: and salts thereof are useful as medicaments, especially for treatment of an angiogenesis-related disease or disorder.

  式中的化合物： 及其盐类可用作药物，特别是用于治疗与血管生成有关的疾病或紊乱。
• ANTI-ANGIOGENIC 2-STYRYL-QUINOLINE COMPOUNDS
  申请人：University College Dublin National University Of Ireland, Dublin

  公开号：EP2877454B1

  公开（公告）日：2016-11-02
• EP3147280B1
  申请人：——

  公开号：EP3147280B1

  公开（公告）日：2018-03-07
• US9388138B2
  申请人：——

  公开号：US9388138B2

  公开（公告）日：2016-07-12