8-(2-phenylethyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide | 1176823-32-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 8-(2-phenylethyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
• 英文别名: 5-Oxido-8-(2-phenylethyl)pyrazolo[5,1-c][1,2,4]benzotriazin-5-ium
• CAS: 1176823-32-7
• 化学式: C₁₇H₁₄N₄O
• 分子量: 290.324
• InChiKey: GPGHQAZJACDLCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 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：
  55.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(2-phenylethyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 在 一氯化碘 作用下， 以 氯仿 为溶剂， 以18%的产率得到3-iodo-8-(2-phenylethyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
  参考文献：
  名称：

  Synthesis, in Vivo Evaluation, and Molecular Modeling Studies of New Pyrazolo[5,1-c][1,2,4]benzotriazine 5-Oxide Derivatives. Identification of a Bifunctional Hydrogen Bond Area Related to the Inverse Agonism

  摘要：

  A new series of pyrazolo[5,1-c-][1,2,4]benzotriazine 5-oxide 8-alkyloxy-/aryloxy-/arylalkyloxy and 8-aryl-/arylalkylderivatives variously substituted at the 3-position were synthesized and binding studies at the benzodiazepine site on GABA(A) receptor were carried out. The pharmacological profile was identified for compounds 10, 11, 16(+), 16(-), and 17 by considering six potential benzodiazepine actions: motor coordination, anticonvulsant action, spontaneous motility and explorative activity, potential anxiolytic-like effects, mouse learning and memory modulation., and finally, ethanol-potentiating action. Compound 17 stands out as the compound that improves mouse memory processes selectively, safely, and in a statistically significant manner. From a ligand-based pharmacophoric model, we identified a hydrogen bond interaction area HBp-3 near the lipophilic area. This new pharmacophoric model allowed us to identify four structural compound typologics and thus to rationalize the affinity data of all compounds.

  DOI：

  10.1021/jm801599a
• 作为产物：
  描述：

  8-iodopyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 、 苯乙基硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以22%的产率得到8-(2-phenylethyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
  参考文献：
  名称：

  Synthesis, in Vivo Evaluation, and Molecular Modeling Studies of New Pyrazolo[5,1-c][1,2,4]benzotriazine 5-Oxide Derivatives. Identification of a Bifunctional Hydrogen Bond Area Related to the Inverse Agonism

  摘要：

  A new series of pyrazolo[5,1-c-][1,2,4]benzotriazine 5-oxide 8-alkyloxy-/aryloxy-/arylalkyloxy and 8-aryl-/arylalkylderivatives variously substituted at the 3-position were synthesized and binding studies at the benzodiazepine site on GABA(A) receptor were carried out. The pharmacological profile was identified for compounds 10, 11, 16(+), 16(-), and 17 by considering six potential benzodiazepine actions: motor coordination, anticonvulsant action, spontaneous motility and explorative activity, potential anxiolytic-like effects, mouse learning and memory modulation., and finally, ethanol-potentiating action. Compound 17 stands out as the compound that improves mouse memory processes selectively, safely, and in a statistically significant manner. From a ligand-based pharmacophoric model, we identified a hydrogen bond interaction area HBp-3 near the lipophilic area. This new pharmacophoric model allowed us to identify four structural compound typologics and thus to rationalize the affinity data of all compounds.

  DOI：

  10.1021/jm801599a

文献信息

• Synthesis, in Vivo Evaluation, and Molecular Modeling Studies of New Pyrazolo[5,1-<i>c</i>][1,2,4]benzotriazine 5-Oxide Derivatives. Identification of a Bifunctional Hydrogen Bond Area Related to the Inverse Agonism
  作者：Gabriella Guerrini、Giovanna Ciciani、Giovanni Cambi、Fabrizio Bruni、Silvia Selleri、Chiara Guarino、Fabrizio Melani、Marina Montali、Claudia Martini、Carla Ghelardini、Monica Norcini、Annarella Costanzo

  DOI：10.1021/jm801599a

  日期：2009.8.13

  A new series of pyrazolo[5,1-c-][1,2,4]benzotriazine 5-oxide 8-alkyloxy-/aryloxy-/arylalkyloxy and 8-aryl-/arylalkylderivatives variously substituted at the 3-position were synthesized and binding studies at the benzodiazepine site on GABA(A) receptor were carried out. The pharmacological profile was identified for compounds 10, 11, 16(+), 16(-), and 17 by considering six potential benzodiazepine actions: motor coordination, anticonvulsant action, spontaneous motility and explorative activity, potential anxiolytic-like effects, mouse learning and memory modulation., and finally, ethanol-potentiating action. Compound 17 stands out as the compound that improves mouse memory processes selectively, safely, and in a statistically significant manner. From a ligand-based pharmacophoric model, we identified a hydrogen bond interaction area HBp-3 near the lipophilic area. This new pharmacophoric model allowed us to identify four structural compound typologics and thus to rationalize the affinity data of all compounds.