N-(1,2,3,4-tetrahydro-1-isoquinolinylmethyl)cyclopentanecarboxamide | 1357104-02-9

• 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: N-(1,2,3,4-tetrahydro-1-isoquinolinylmethyl)cyclopentanecarboxamide
• 英文别名: N-(1,2,3,4-tetrahydro-1-isoquinolin-1-ylmethyl)cyclopentanecarbamide；N-(1,2,3,4-tetrahydroisoquinolin-1-ylmethyl)cyclopentanecarboxamide
• CAS: 1357104-02-9
• 化学式: C₁₆H₂₂N₂O
• 分子量: 258.363
• InChiKey: PYYLZXCVSMUUAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1,2,3,4-tetrahydro-1-isoquinolinylmethyl)cyclopentanecarboxamide 、 氯乙酰氯 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以82%的产率得到2-(cyclopentanecarbonyl)-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one
  参考文献：
  名称：

  Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis

  摘要：

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.108
• 作为产物：
  描述：

  tert-butyl 1-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 吡啶 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(1,2,3,4-tetrahydro-1-isoquinolinylmethyl)cyclopentanecarboxamide
  参考文献：
  名称：

  Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis

  摘要：

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.108

文献信息

• HETEROCYCLIC COMPOUNDS AND USE THEREOF
  申请人：National Health Research Institutes

  公开号：US20190077786A1

  公开（公告）日：2019-03-14

  Disclosed are compounds of formula (I) below or pharmaceutically acceptable salts thereof: in which each of variables R 1 -R 6 , L, m, and n is defined herein. Also disclosed are a method for treating an opioid receptor-associated condition with a compound of formula (I) and a pharmaceutical composition containing same.

  揭示了下面的化合物的结构式（I）或其药用盐：其中变量R1-R6、L、m和n在此处有定义。还揭示了使用结构式（I）的化合物治疗阿片受体相关疾病的方法，以及含有该化合物的药物组合物。
• Tetrahydroisoquinolines for use as MOR/NOP dual agonists
  申请人：National Health Research Institutes

  公开号：US10597378B2

  公开（公告）日：2020-03-24

  Disclosed are compounds of formula (I) below or pharmaceutically acceptable salts thereof: in which each of variables R1-R6, L, m, and n is defined herein. Also disclosed are a method for treating an opioid receptor-associated condition with a compound of formula (I) and a pharmaceutical composition containing same.

  所公开的是下式 (I) 的化合物或其药学上可接受的盐类： 其中各变量 R1-R6、L、m 和 n 在本文中定义。还公开了一种用式（I）化合物和含有该化合物的药物组合物治疗阿片受体相关病症的方法。
• TW2019/12628
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of new praziquantel analogues: Potential candidates for the treatment of schistosomiasis
  作者：Partha Sarathi Sadhu、Singam Naveen Kumar、Malapaka Chandrasekharam、Livia Pica-Mattoccia、Donato Cioli、Vaidya Jayathirtha Rao

  DOI：10.1016/j.bmcl.2011.11.108

  日期：2012.1

  An efficient synthesis of antischistosomal drug praziquantel and analogues was achieved and the synthetic route designed was to afford structurally diverse analogues for better structure-activity relationship understanding. Total of nineteen PZQ analogues with structural variations at amide, piperazine and aromatic moieties have been synthesized and fully characterized. Among all the new analogues tested for antischistosomal activity, one dimethoxy tetrahydroisoquinoline analogue and two tetrahydro-beta-carboline analogues exhibited moderate activity against adult Schistosoma mansoni. Tetrahydro-beta-carboline analogues showed moderate activity whereas the presence of p-trifluoromethylbenzoyl and p-toluenesulphonyl moieties resulted in complete suppression of antischistosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.