3-methyl-8-benzyloxypyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide | 1352328-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methyl-8-benzyloxypyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
• 英文别名: 3-Methyl-5-oxido-8-phenylmethoxypyrazolo[5,1-c][1,2,4]benzotriazin-5-ium；3-methyl-5-oxido-8-phenylmethoxypyrazolo[5,1-c][1,2,4]benzotriazin-5-ium
• CAS: 1352328-81-4
• 化学式: C₁₇H₁₄N₄O₂
• 分子量: 306.324
• InChiKey: DOLYCIMBMMTGHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-8-benzyloxypyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 在 溶剂黄146 、 锌 作用下， 以68%的产率得到3-methyl-8-benzyloxypyrazolo[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：

  1-(2-nitro-5-chlorophenyl)-4-methyl-5-aminopyrazole 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 二乙二醇二甲醚 、 水 为溶剂， 反应 44.0h， 生成 3-methyl-8-benzyloxypyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
  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

文献信息

• 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.