2-(3-methoxyphenyl)-2H-pyrazolo[3,4-c]quinolin-4(5H)-one | 950822-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-methoxyphenyl)-2H-pyrazolo[3,4-c]quinolin-4(5H)-one
• 英文别名: 2-(3-methoxyphenyl)-5H-pyrazolo[3,4-c]quinolin-4-one
• CAS: 950822-49-8
• 化学式: C₁₇H₁₃N₃O₂
• 分子量: 291.309
• InChiKey: QCEZYGVYMOEOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)-2H-pyrazolo[3,4-c]quinolin-4(5H)-one 在 五氯化磷 、 氨 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(3-methoxyphenyl)-2H-pyrazolo[3,4-c]quinolin-4-amine
  参考文献：
  名称：

  New 2-Arylpyrazolo[3,4-c]quinoline Derivatives as Potent and Selective Human A₃ Adenosine Receptor Antagonists. Synthesis, Pharmacological Evaluation, and Ligand−Receptor Modeling Studies

  摘要：

  This paper reports the study of some 2-arylpyrazolo[3,4-c]quinolin-4-ones, 4-amines, and 4-amino-substituted derivatives designed as human A(3) adenosine receptor (AR) antagonists. Most of the herein reported compounds showed a nanomolar affinity toward the hA(3) receptor subtype and different degrees of selectivity that resulted to be strictly dependent on the presence and nature of the substituent on the 4-amino group. Bulky and lipophilic acyl groups, as well as the benzylcarbamoyl residue, afforded highly potent and selective hA(3) receptor antagonists. The selected 4-diphenylacetylamino-2-phenylpyrazoloquinoline (25) and 4-dibenzoylamino-2-(4-methoxyphenyl)pyrazoloquinoline (36), tested in an in vitro rat model of cerebral ischemia, prevented the irreversible failure of synaptic activity induced by oxygen and glucose deprivation in the hippocampus. The observed structure-affinity relationships of this class of antagonists were also exhaustively rationalized using the recently published ligand-based homology modeling (LBHM) approach.

  DOI：

  10.1021/jm070123v
• 作为产物：
  描述：

  2-氧代-3-吲哚羧酸乙酯 、 3-甲氧基苯肼盐酸 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.1h， 以80%的产率得到2-(3-methoxyphenyl)-2H-pyrazolo[3,4-c]quinolin-4(5H)-one
  参考文献：
  名称：

  New 2-Arylpyrazolo[3,4-c]quinoline Derivatives as Potent and Selective Human A₃ Adenosine Receptor Antagonists. Synthesis, Pharmacological Evaluation, and Ligand−Receptor Modeling Studies

  摘要：

  This paper reports the study of some 2-arylpyrazolo[3,4-c]quinolin-4-ones, 4-amines, and 4-amino-substituted derivatives designed as human A(3) adenosine receptor (AR) antagonists. Most of the herein reported compounds showed a nanomolar affinity toward the hA(3) receptor subtype and different degrees of selectivity that resulted to be strictly dependent on the presence and nature of the substituent on the 4-amino group. Bulky and lipophilic acyl groups, as well as the benzylcarbamoyl residue, afforded highly potent and selective hA(3) receptor antagonists. The selected 4-diphenylacetylamino-2-phenylpyrazoloquinoline (25) and 4-dibenzoylamino-2-(4-methoxyphenyl)pyrazoloquinoline (36), tested in an in vitro rat model of cerebral ischemia, prevented the irreversible failure of synaptic activity induced by oxygen and glucose deprivation in the hippocampus. The observed structure-affinity relationships of this class of antagonists were also exhaustively rationalized using the recently published ligand-based homology modeling (LBHM) approach.

  DOI：

  10.1021/jm070123v

文献信息

• New 2-Arylpyrazolo[3,4-<i>c</i>]quinoline Derivatives as Potent and Selective Human A₃ Adenosine Receptor Antagonists. Synthesis, Pharmacological Evaluation, and Ligand−Receptor Modeling Studies
  作者：Vittoria Colotta、Daniela Catarzi、Flavia Varano、Francesca Capelli、Ombretta Lenzi、Guido Filacchioni、Claudia Martini、Letizia Trincavelli、Osele Ciampi、Anna Maria Pugliese、Felicita Pedata、Andrea Schiesaro、Erika Morizzo、Stefano Moro

  DOI：10.1021/jm070123v

  日期：2007.8.1

  This paper reports the study of some 2-arylpyrazolo[3,4-c]quinolin-4-ones, 4-amines, and 4-amino-substituted derivatives designed as human A(3) adenosine receptor (AR) antagonists. Most of the herein reported compounds showed a nanomolar affinity toward the hA(3) receptor subtype and different degrees of selectivity that resulted to be strictly dependent on the presence and nature of the substituent on the 4-amino group. Bulky and lipophilic acyl groups, as well as the benzylcarbamoyl residue, afforded highly potent and selective hA(3) receptor antagonists. The selected 4-diphenylacetylamino-2-phenylpyrazoloquinoline (25) and 4-dibenzoylamino-2-(4-methoxyphenyl)pyrazoloquinoline (36), tested in an in vitro rat model of cerebral ischemia, prevented the irreversible failure of synaptic activity induced by oxygen and glucose deprivation in the hippocampus. The observed structure-affinity relationships of this class of antagonists were also exhaustively rationalized using the recently published ligand-based homology modeling (LBHM) approach.