3-Methyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide | 1352328-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-Methyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
• 英文别名: 8-Chloro-3-methyl-5-oxidopyrazolo[5,1-c][1,2,4]benzotriazin-5-ium；8-chloro-3-methyl-5-oxidopyrazolo[5,1-c][1,2,4]benzotriazin-5-ium
• CAS: 1352328-80-3
• 化学式: C₁₀H₇ClN₄O
• 分子量: 234.645
• InChiKey: AEOPHACTIUMBPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3-methyl-8-benzylaminopyrazolo[5,1-c][1,2,4]benzotriazine
  参考文献：
  名称：

  Development of ligands at γ-aminobutyrric acid type A (GABAA) receptor subtype as new agents for pain relief

  摘要：

  The identification of compounds with selective anxiolytic-like effects, exerted through the benzodiazepine site on gamma-aminobutyric acid type A (GABA(A)) receptors, and that show pronounced antihyperalgesia in several pain models, has oriented research towards the development of new agents for the relief of pain. Starting from our previously reported ligands at the benzodiazepine site on GABA(A) receptors showing selective anxiolytic-like effects, we have designed new compounds with the aim of identifying those devoid of the typical side effects of the classical benzodiazepines. Our preliminary results indicate that compounds 4, 10(+/-) and 11 have a very promising antihyperalgesic profile in different animal pain models (peripheral mono-neuropathy, STZ-induced hyperalgesia). In particular 11 exhibits high potency since it exerted its protective effect starting from the dose of 3 mg/kg po, after single injection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.047
• 作为产物：
  描述：

  3-carboxy-8-chloropyrazolo<5,1-c><1,2,4>benzotriazine 5-oxide 在 dimethyl sulfide borane 、 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3-Methyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
  参考文献：
  名称：

  吡唑并[5,1- c ] [1,2,4]苯并三嗪核作用于γ-氨基丁酸A型（GABA A）受体的新型认知增强剂的合成

  摘要：

  与衰老，神经退行性疾病和精神疾病相关的记忆功能障碍代表了日益增长的医疗需求。探索学习和记忆基础的生物学机制的研究进展为开发针对选择性神经元靶标的记忆增强疗法开辟了新的潜在方法。在这项工作中，我们合成了一些具有吡唑并[5,1- c ] [1,2,4]苯并三嗪核心的衍生物，以鉴定具有增强潜力的GABA A受体亚型（GABA A受体上的苯二氮卓部位）上的配体无副作用的认知活动通常与非选择性GABA A调节剂有关。实际上，有很多证据表明GABA A-R（γ-氨基丁酸，A型受体）亚型配体与学习和记忆有关。已经进行了体外和体内测试。药理学数据表明，化合物7，13，14和22充当GABA的双重功能调节剂阿-Rs（promnemonic和抗焦虑药），而仅化合物3和10立场选择性地显示良好antiamnesic和促认知活性（1和3mg /公斤）。

  DOI：

  10.1016/j.bmc.2013.02.027

文献信息

• Synthesis of novel cognition enhancers with pyrazolo[5,1- c ][1,2,4]benzotriazine core acting at γ-aminobutyric acid type A (GABA A ) receptor
  作者：Gabriella Guerrini、Giovanna Ciciani、Annarella Costanzo、Simona Daniele、Claudia Martini、Carla Ghelardini、Lorenzo Di Cesare Mannelli、Samuele Ciattini

  DOI：10.1016/j.bmc.2013.02.027

  日期：2013.4

  with a pyrazolo[5,1-c][1,2,4]benzotriazine core to identify ligands on GABAA receptors subtype (benzodiazepine site on GABAA-receptor) endowed with the potential of enhancing cognition activity without the side effects usually associated with non-selective GABAA modulators. In fact, there is much evidence that GABAA-R (γ-aminobutyric acid, type A receptor) subtype ligands have relevance in learning

  与衰老，神经退行性疾病和精神疾病相关的记忆功能障碍代表了日益增长的医疗需求。探索学习和记忆基础的生物学机制的研究进展为开发针对选择性神经元靶标的记忆增强疗法开辟了新的潜在方法。在这项工作中，我们合成了一些具有吡唑并[5,1- c ] [1,2,4]苯并三嗪核心的衍生物，以鉴定具有增强潜力的GABA A受体亚型（GABA A受体上的苯二氮卓部位）上的配体无副作用的认知活动通常与非选择性GABA A调节剂有关。实际上，有很多证据表明GABA A-R（γ-氨基丁酸，A型受体）亚型配体与学习和记忆有关。已经进行了体外和体内测试。药理学数据表明，化合物7，13，14和22充当GABA的双重功能调节剂阿-Rs（promnemonic和抗焦虑药），而仅化合物3和10立场选择性地显示良好antiamnesic和促认知活性（1和3mg /公斤）。
• Development of ligands at γ-aminobutyrric acid type A (GABAA) receptor subtype as new agents for pain relief
  作者：Gabriella Guerrini、Giovanna Ciciani、Fabrizio Bruni、Silvia Selleri、Claudia Martini、Simona Daniele、Carla Ghelardini、Lorenzo Di Cesare Mannelli、Annarella Costanzo

  DOI：10.1016/j.bmc.2011.10.047

  日期：2011.12

  The identification of compounds with selective anxiolytic-like effects, exerted through the benzodiazepine site on gamma-aminobutyric acid type A (GABA(A)) receptors, and that show pronounced antihyperalgesia in several pain models, has oriented research towards the development of new agents for the relief of pain. Starting from our previously reported ligands at the benzodiazepine site on GABA(A) receptors showing selective anxiolytic-like effects, we have designed new compounds with the aim of identifying those devoid of the typical side effects of the classical benzodiazepines. Our preliminary results indicate that compounds 4, 10(+/-) and 11 have a very promising antihyperalgesic profile in different animal pain models (peripheral mono-neuropathy, STZ-induced hyperalgesia). In particular 11 exhibits high potency since it exerted its protective effect starting from the dose of 3 mg/kg po, after single injection. (C) 2011 Elsevier Ltd. All rights reserved.