(S)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

• 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: (S)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one
• 英文别名: 2-[(2S)-1-hydroxypropan-2-yl]-5-nitroisoquinolin-1-one
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: MLORHOHNTRJWCX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 2-(adamantan-1-yl)-N-(2-((S)-1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)acetamide
  参考文献：
  名称：

  The role of polycyclic frameworks in modulating P2X7 receptor function

  摘要：

  Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.10.075
• 作为产物：
  描述：

  2-甲基-3-硝基苯甲酸 在 硫酸 、 silica gel 、 三甲胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 (S)-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one
  参考文献：
  名称：

  The role of polycyclic frameworks in modulating P2X7 receptor function

  摘要：

  Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.10.075

文献信息

• Bicycloheteroaryl Compounds as P2X7 Modulators and Uses Thereof
  申请人：Kelly Michael G.

  公开号：US20100184802A1

  公开（公告）日：2010-07-22

  Bicycloheteroaryl compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.

  本发明揭示了具有以下式子表示的Bicycloheteroaryl化合物：这些化合物可以制备成药物组合物，并可用于预防和治疗哺乳动物包括人类的各种情况，包括但不限于疼痛，炎症，创伤性损伤等。
• Bicycloheteroaryl compounds as P2X7 modulators and uses thereof
  申请人：Kelly Michael G.

  公开号：US20110092476A1

  公开（公告）日：2011-04-21

  Bicycloheteroaryl compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.

  本文披露了一类具有以下公式的双环杂环芳基化合物：这些化合物可作为药物成分制备药物组合物，用于预防和治疗哺乳动物，包括人类的多种疾病，例如疼痛、炎症、创伤等，但不限于此。
• [EN] BICYCLOHETEROARYL COMPOUNDS AS P2X7 MODULATORS AND USES THEREOF<br/>[FR] COMPOSÉS DE BICYCLOHÉTÉROARYLE EN TANT QUE MODULATEUR DE P2X7 ET LEURS UTILISATIONS
  申请人：RENOVIS INC

  公开号：WO2007109201A2

  公开（公告）日：2007-09-27

  [EN] Bicycloheteroaryl compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, traumatic injury, and others.
  [FR] La présente invention concerne des composés de bicyclohétéroaryle de formule (I). Ces composés peuvent être préparés sous la forme de compositions pharmaceutiques et peuvent être utilisés pour prévenir et traiter chez des mammifères, y compris chez l'homme, un certain nombre d'états pathologiques comprenant, entre autres, la douleur, l'inflammation, les blessures traumatiques, etc.
• The role of polycyclic frameworks in modulating P2X7 receptor function
  作者：Timothy B. Callis、Tristan A. Reekie、James O'Brien-Brown、Erick C.N. Wong、Eryn L. Werry、Nabiha Elias、William T. Jorgensen、John Tsanaktsidis、Louis M. Rendina、Michael Kassiou

  DOI：10.1016/j.tet.2017.10.075

  日期：2018.3

  Herein we describe our recent attempts to target the P2X7 receptor for potential treatment of neurological disorders. This work focusses on different polycycles including carborane, adamantane or cubane, joined by either a cyanoguanidine or an amide linker to phenyl or isoquinoline moieties. We have demonstrated the superiority of the adamantyl moiety over other polycycles in terms of synthetic accessibility and biological (cellular) activity. We have also shown that an amide or cyanoguanidine linker can greatly alter the biological activity of compounds. This SAR study provides important insights into the types of functionality required to target the P2X7 receptor. (C) 2017 Elsevier Ltd. All rights reserved.