5,8-二氯-1,2,3,4-四氢异喹啉 | 89315-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 5,8-二氯-1,2,3,4-四氢异喹啉
• 英文名称: 5,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
• CAS: 89315-57-1
• 化学式: C₉H₉Cl₂N
• 分子量: 202.083
• InChiKey: GNGZYQIBMKXWKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 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：

  5,8-二氯-1,2,3,4-四氢异喹啉 、 2-氯甲基咪唑啉盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 5,8-dichloro-2-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3,4-dihydro-1H-isoquinoline
  参考文献：
  名称：

  2-（四氢异喹啉-2-基甲基）-和2-（异吲哚-2-基甲基）咪唑啉对α-肾上腺素受体的亲和力。咪唑啉对[3H]咪唑烷标记的α2-肾上腺素受体与[3H]育亨宾标记的部位的亲和力不同。

  摘要：

  制备一系列2-（四氢异喹啉-2-基甲基）-和2-（异吲哚-2-基甲基）咪唑啉，并通过放射性配体结合测试α1-和α2-肾上腺素受体的亲和力。几种化合物5-氟-（5h），5-氯-（5j），5,8-二甲氧基-（5r）和5,8-二甲氧基-（5r），1-甲基-（5s）2-（基于[3H]育亨宾从大鼠大脑皮膜的置换，发现四氢异喹啉-2-基甲基）咪唑啉是选择性的α2-肾上腺素受体配体。一种化合物2-[（（8-氯四氢异喹啉-2-基）甲基]咪唑啉（5m）与[3H]育亨宾相比，对[3H] idazoxan标记的α2-肾上腺素受体的亲和力显示出36倍的差异-标记的位点，可能是α2-肾上腺素受体亚型的证据。

  DOI：

  10.1021/jm00164a021
• 作为产物：
  描述：

  5,8-二氯异喹啉 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、413.68 kPa 条件下， 生成 5,8-二氯-1,2,3,4-四氢异喹啉
  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

• Phenyl benzenesulfonamides are novel and selective 5-HT6 antagonists: identification of N-(2,5-dibromo-3-fluorophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide (SB-357134)
  作者：Steven M Bromidge、Stephen E Clarke、Tracey Gager、Kerry Griffith、Phillip Jeffrey、Andrew J Jennings、Graham F Joiner、Frank D King、Peter J Lovell、Stephen F Moss、Helen Newman、Graham Riley、Derek Rogers、Carol Routledge、Halina Serafinowska、Douglas R Smith

  DOI：10.1016/s0960-894x(00)00597-7

  日期：2001.1

  Substituted N-phenyl-4-methoxy-3-piperazin-1-ylbenzenesulfonamides and conformationally restricted analogues have been identified as high affinity and selective 5-HT6 antagonists. Compounds from this series had a range of pharmacokinetic profiles in rat and in general there was a correlation between clearance and CNS penetration. Based on its overall biological profile 2 (SB-357134) was selected for further pre-clinical evaluation. (C) 2000 Elsevier Science Ltd. All rights reserved.
• SULPHONAMIDE DERIVATIVES BEING 5-HT6 RECEPTOR ANTAGONISTS AND PROCESS FOR THEIR PREPARATION
  申请人：SmithKline Beecham plc

  公开号：EP0994862B1

  公开（公告）日：2005-06-01