3-ethoxycarbonyl-8-chloropyrazolo<5,1-c><1,2,4>benzotriazine 5-oxide | 161464-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-ethoxycarbonyl-8-chloropyrazolo<5,1-c><1,2,4>benzotriazine 5-oxide
• 英文别名: ethyl 8-chloropyrazolo[5,1-c][1,2,4]benzotriazine-3-carboxylate 5-oxide；3-ethoxycarbonyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide；Ethyl 8-chloro-5-oxido-pyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-3-carboxylate；ethyl 8-chloro-5-oxidopyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-3-carboxylate
• CAS: 161464-23-9
• 化学式: C₁₂H₉ClN₄O₃
• 分子量: 292.681
• InChiKey: UIZFETTXADXHMI-UHFFFAOYSA-N

物化性质

• 沸点：
  350.739±47.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.619±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-8-chloropyrazolo<5,1-c><1,2,4>benzotriazine 5-oxide 在 亚磷酸三乙酯 作用下， 以 甲苯 为溶剂， 以87%的产率得到ethyl 8-chloropyrazolo<5,1-c><1,2,4>benzotriazine-3-carboxylate
  参考文献：
  名称：

  Benzodiazepine receptor ligands. Synthesis and pharmacological evaluation of 3-, 7- and 8-substituted [5,1-c][1,2,4]benzotriazines and 5-oxide derivatives. Part I

  摘要：

  A new series of 3-, 7- and 8-substituted pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides and a series of pyrazolo[5,1-c][1,2,4]benzotriazines were synthesized and their benzodiazepine receptor affinities were evaluated in vitro. A study of structure-affinity relationships within the series is briefly discussed, considering the role of various substituents at the 3-, 7- and 8-positions and the role of N-5-oxide. Compounds 1b, 1c, 1cR, 4c, 4cR, 9d, 12d and 12dR were evaluated in vivo for their anticonvulsant effects.

  DOI：

  10.1016/0223-5234(96)80363-1
• 作为产物：
  描述：

  2-硝基-5-氯苯基肼 在 sodium hydroxide 、 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 3-ethoxycarbonyl-8-chloropyrazolo<5,1-c><1,2,4>benzotriazine 5-oxide
  参考文献：
  名称：

  1-（2-硝基苯基）-5-氨基吡唑在碱性条件下的反应性和新的3-，7-和8-取代的吡唑并[5,1- c ] [1,2,4]苯并三嗪5-氧化物的合成，作为苯二氮杂receptor受体配体

  摘要：

  对1-（2-硝基苯基）-5-氨基吡唑在碱性条件下的反应进行了重新研究，并通过光谱法证实了所获得的吡唑并[5,1- c ] [1,2,4]苯并三嗪5-氧化物的结构。特别地，确定了对8-氯衍生物4a和6a以及7-硝基衍生物11a和12a的不同芳族亲核攻击。从这些后面的化合物意外（苯基ONN -azoxy）吡唑类中分离得到。

  DOI：

  10.1002/jhet.5570310612

文献信息

• Costanzo; Guerrini; Ciciani, Medicinal Chemistry Research, 1999, vol. 9, # 5, p. 322 - 339
  作者：Costanzo、Guerrini、Ciciani、Bruni、Selleri、Costa、Martini、Lucacchini、Malmberg Aiello、Ipponi

  DOI：——

  日期：——
• 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.