5-methoxy-3-(2-nitroethyl)-2-phenylpyrazolo[1,5-a]pyridine | 877994-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-methoxy-3-(2-nitroethyl)-2-phenylpyrazolo[1,5-a]pyridine
• CAS: 877994-12-2
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: PKWAQDXVKCEXDG-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-(2-nitroethyl)-2-phenylpyrazolo[1,5-a]pyridine 在 tin 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 72.0h， 生成 N-[2-(5-methoxy-2-phenylpyrazolo[1,5-a]pyridin-3-yl)ethyl]butanamide
  参考文献：
  名称：

  Bicyclic melatonin receptor agonists containing a ring-junction nitrogen: Synthesis, biological evaluation, and molecular modeling of the putative bioactive conformation

  摘要：

  Employing 1,3-dipolar cycloaddition for the synthesis of the 7a-azaindole nucleus, analogues of melatonin have been synthesized and tested against human and amphibian melatonin receptors. Introducing a phenyl substituent ill position 2 of the heterocyclic moiety significantly increased binding affinity to both the MT1 and MT2 receptors. Shifting the methoxy group from position 5 to 2 of the 7a-azaindole ring led to a substantial reduction of MT1 binding when MT2 recognition was maintained. We theoretically investigated the hypothesis whether the 2-methoxy function of the azamelatonin analogue 27 is able to mimic the 5-methoxy group of the neurohormone by directing its 2-methoxy function toward the methoxy binding site. DFT calculations and experimental binding differences of analogue compounds indicate that the energy gained by forming the methoxy-specific hydrogen-bond interaction should exceed the energy required for adopting ail alternative conformation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.042
• 作为产物：
  描述：

  5-methoxy-2-phenylpyrazolo[1,5-a]pyridine 在 sodium tetrahydroborate 、 盐酸甲胺 、 potassium acetate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 241.83h， 生成 5-methoxy-3-(2-nitroethyl)-2-phenylpyrazolo[1,5-a]pyridine
  参考文献：
  名称：

  Bicyclic melatonin receptor agonists containing a ring-junction nitrogen: Synthesis, biological evaluation, and molecular modeling of the putative bioactive conformation

  摘要：

  Employing 1,3-dipolar cycloaddition for the synthesis of the 7a-azaindole nucleus, analogues of melatonin have been synthesized and tested against human and amphibian melatonin receptors. Introducing a phenyl substituent ill position 2 of the heterocyclic moiety significantly increased binding affinity to both the MT1 and MT2 receptors. Shifting the methoxy group from position 5 to 2 of the 7a-azaindole ring led to a substantial reduction of MT1 binding when MT2 recognition was maintained. We theoretically investigated the hypothesis whether the 2-methoxy function of the azamelatonin analogue 27 is able to mimic the 5-methoxy group of the neurohormone by directing its 2-methoxy function toward the methoxy binding site. DFT calculations and experimental binding differences of analogue compounds indicate that the energy gained by forming the methoxy-specific hydrogen-bond interaction should exceed the energy required for adopting ail alternative conformation. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.042