5-甲氧基-2-苯基吡唑并[1,5-a]吡啶-3-羧酸乙酯 | 403495-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-甲氧基-2-苯基吡唑并[1,5-a]吡啶-3-羧酸乙酯
• 英文名称: ethyl 5-methoxy-2-phenylpyrazolo[1,5-a]pyridine-3-carboxylate
• CAS: 403495-91-0
• 化学式: C₁₇H₁₆N₂O₃
• 分子量: 296.326
• InChiKey: DSELVVRRLKPIRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2-苯基吡唑并[1,5-a]吡啶-3-羧酸乙酯 在 硫酸 作用下， 反应 16.0h， 以80%的产率得到5-methoxy-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
• 作为产物：
  描述：

  N-amino-4-methoxypyridinium 2,4-dinitrophenolate 、 苯丙炔酸乙酯 在 air 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以35%的产率得到5-甲氧基-2-苯基吡唑并[1,5-a]吡啶-3-羧酸乙酯
  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

文献信息

• Pyrazolopyridine compound and pharmaceutical use thereof
  申请人：——

  公开号：US20040110763A1

  公开（公告）日：2004-06-10

  A pyrazolopyridine compound of formula (I) wherein: R 1 is hydrogen, lower alkyl optionally substituted by susbtituent(s), or cyclo(lower)alkyl which may be interrupted by an oxygen or nitrogen atom and optionally substituted by substituent(s); R 2 is hydrogen, halogen or lower alkoxy; R 3 is a substituent; and n is an integer from 1 to 4, provided R 3 may be different from each other when n is 2, 3 or 4, or a salt thereof. The pyrazolopyridine compound (I) and salt thereof of the present invention are adnosine antagonists and are useful for the prevention and/or treatment of depression, dementia (e.g. Alzheimer's disease, cerebrovascular dementia, dementia accompanying Parkinson's disease, etc.) Parkinson's disease, anxiety, pain, cerebrovascular disease (e.g. stroke, etc.), heart failure and the like. 1

  化合物(I)为吡唑吡啶化合物，其化学式为：其中，R1为氢、低碳基（可选择性地被取代）或环（低）烷基，其可由氧或氮原子中断，且可选择性地被取代；R2为氢、卤素或低烷氧基；R3为取代基；n为1至4的整数，但当n为2、3或4时，R3可能彼此不同，或其盐。本发明的吡唑吡啶化合物(I)及其盐为腺苷受体拮抗剂，可用于预防和/或治疗抑郁症、痴呆症（例如阿尔茨海默病、脑血管痴呆、帕金森病伴随痴呆等）、帕金森病、焦虑症、疼痛、脑血管疾病（例如中风等）、心力衰竭等疾病。
• Bicyclic melatonin receptor agonists containing a ring-junction nitrogen: Synthesis, biological evaluation, and molecular modeling of the putative bioactive conformation
  作者：Jan Elsner、Frank Boeckler、Kathryn Davidson、David Sugden、Peter Gmeiner

  DOI：10.1016/j.bmc.2005.10.042

  日期：2006.3

  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.