5,6,7,8-Tetrachloroisoquinoline | 73075-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,6,7,8-Tetrachloroisoquinoline
• CAS: 73075-65-7
• 化学式: C₉H₃Cl₄N
• 分子量: 266.942
• InChiKey: BCRBPDLMPKWIGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6,7,8-Tetrachloroisoquinoline 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 5,6,7,8-Tetrachloro-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007
• 作为产物：
  描述：

  异喹啉 在 三氯化铝 、 氯 作用下， 反应 12.0h， 以1.5 g的产率得到5,6,7,8-Tetrachloroisoquinoline
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007

文献信息

• 19F NMR spectroscopy of polyhalonaphthalenes
  作者：Raymond S. Matthews、Adam N. Matthews

  DOI：10.1016/s0022-1139(00)00260-8

  日期：2000.7

  isoquinolines (5,6,7,8-tetrachloro-,3,5,6,7,8-pentachloro-,3,4,5,6,7,8-hexachloro- and 1,3,4,5,6,7,8-heptachloro-isoquinoline) led to the preparation of 15 new polychloropolyfluoro isoquinolines by reaction with caesium fluoride in DMSO at 100°C. The product from the perchloroisoquinoline was an inseparable mixture of C9Cl7−nFnN where n is 1–3. The order of reactivity in 1,3,4,5,6,7,8-heptachloro-isoquinoline

  四个异喹啉（5,6,7,8-四氯-，3,5,6,7,8-五氯-，3,4,5,6,7,8-六氯和1， 3,4,5,6,7,8-七氯异喹啉通过在100°C的DMSO中与氟化铯反应制备了15种新的多氯多氟异喹啉。全氯异喹啉的产物是C 9 Cl 7- n F n N的不可分离的混合物，其中n为1-3。1,3,4,5,6,7,8-七氯异喹啉[10]对氟化物的亲核攻击的反应顺序为1⪢6= 7 = 8 = 3> 5 = 4
• BONDINELL W. E.; CHAPIN F. W.; GIRARD G. R.; KAISER C.; KROG A. J.; PAVLO+, J. MED. CHEM., 1980, 23, NO 5, 506-511
  作者：BONDINELL W. E.、 CHAPIN F. W.、 GIRARD G. R.、 KAISER C.、 KROG A. J.、 PAVLO+

  DOI：——

  日期：——