5,6,7,8-Tetrachloro-1,2,3,4-tetrahydro-isoquinoline | 82771-67-3

• 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: 5,6,7,8-Tetrachloro-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 5,6,7,8-Tetrachloro-1,2,3,4-tetrahydroisoquinoline
• CAS: 82771-67-3
• 化学式: C₉H₇Cl₄N
• 分子量: 270.973
• InChiKey: BUKGFYLSZBAHLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6,7,8-Tetrachloro-1,2,3,4-tetrahydro-isoquinoline 在 亚氨基二砜氯化物 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 以52%的产率得到5,6,7,8-tetrachloro-N-[(5,6,7,8-tetrachloro-3,4-dihydro-1H-isoquinolin-2-yl)sulfonyl]-3,4-dihydro-1H-isoquinoline-2-sulfonamide
  参考文献：
  名称：

  亚氨基二硫酰胺。2.取代的1,2,3,4-四氢异喹啉基磺酰亚胺作为慢反应性过敏性物质的拮抗剂。

  摘要：

  作为研究N'，N'-双（芳烷基）亚氨基二硫酰胺的结构修饰对其选择性拮抗SRS-A活性能力的影响的一部分，研究了一些构象受限的结构。在这些具有构象受限的亚烷基侧链的衍生物中，取代的1,2,3,4-四氢异喹啉基磺酰亚胺产生了最佳的SRS-A拮抗剂活性和选择性。测试了这些化合物对部分纯化的SRS-A诱导的豚鼠回肠收缩的拮抗作用。在这一系列四氢异喹啉中，研究了芳环取代以及杂环尺寸的取代和变化对SRS-A拮抗剂活性和选择性的影响。

  DOI：

  10.1021/jm00352a028
• 作为产物：
  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

文献信息

• ALI, FADIA, EL-FEHAIL;GLEASON, J. G.;HILL, D. T.;KRELL, R. D.;KRUSE, C. H+, J. MED. CHEM., 1982, 25, N 10, 1235-1240
  作者：ALI, FADIA, EL-FEHAIL、GLEASON, J. G.、HILL, D. T.、KRELL, R. D.、KRUSE, C. H+

  DOI：——

  日期：——
• Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines
  作者：William E. Bondinell、Frederic W. Chapin、Gerald R. Girard、Carl Kaiser、Arnold J. Krog、Alex M. Pavloff、Mark S. Schwartz、Joanne S. Silvestri、Praful D. Vaidya

  DOI：10.1021/jm00179a007

  日期：1980.5

  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.
• Imidodisulfamides. 2. Substituted 1,2,3,4-tetrahydroisoquinolinylsulfonic imides as antagonists of slow-reacting substance of anaphylaxis
  作者：Fadia El-Fehail Ali、John G. Gleason、David T. Hill、Robert D. Krell、Carolyn H. Kruse、Patricia G. Lavanchy、Beth W. Volpe

  DOI：10.1021/jm00352a028

  日期：1982.10

  N'-bis(aralkyl)imidodisulfamides on their ability to selectively antagonize SRS-A activity, a few conformationally constrained structures were examined. Among these derivatives having a conformationally restricted alkylene side chain, substituted 1,2,3,4-tetrahydroisoquinolinylsulfonic imides produced optimum SRS-A antagonist activity and selectivity. These compounds were tested for antagonism of partially

  作为研究N'，N'-双（芳烷基）亚氨基二硫酰胺的结构修饰对其选择性拮抗SRS-A活性能力的影响的一部分，研究了一些构象受限的结构。在这些具有构象受限的亚烷基侧链的衍生物中，取代的1,2,3,4-四氢异喹啉基磺酰亚胺产生了最佳的SRS-A拮抗剂活性和选择性。测试了这些化合物对部分纯化的SRS-A诱导的豚鼠回肠收缩的拮抗作用。在这一系列四氢异喹啉中，研究了芳环取代以及杂环尺寸的取代和变化对SRS-A拮抗剂活性和选择性的影响。