2,5-dihydro-2-methyl-4H-pyrazolo[3,4-c]quinolin-4-one | 142598-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,5-dihydro-2-methyl-4H-pyrazolo[3,4-c]quinolin-4-one
• 英文别名: 2-methyl-5H-pyrazolo[3,4-c]quinolin-4-one
• CAS: 142598-37-6
• 化学式: C₁₁H₉N₃O
• 分子量: 199.212
• InChiKey: ONQSELGPEBXWIK-UHFFFAOYSA-N

物化性质

• 沸点：
  306.8±11.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-dihydro-2-methyl-4H-pyrazolo[3,4-c]quinolin-4-one 在 五氯化磷 、 三氯氧磷 作用下， 反应 3.0h， 生成 4-chloro-2-methylpyrazoloquinolone
  参考文献：
  名称：

  Synthesis, structure–affinity relationships, and molecular modeling studies of novel pyrazolo[3,4-c]quinoline derivatives as adenosine receptor antagonists

  摘要：

  This paper reports the study of new 2-phenyl- and 2-methylpyrazolo[3,4-c]quinolin-4-ones (series A) and 4-amines (series B), designed as adenosine receptor (AR) antagonists. The synthesized compounds bear at the 6-position various groups, with different lipophilicity and steric hindrance, that were thought to increase human A(1) and A(2A) AR affinities and selectivities, with respect to those of the parent 6-unsubstituted compounds. In series A, this modification was not tolerated since it reduced AR affinity, while in series B it shifted the binding towards the hA(1) subtype. To rationalize the observed structure-affinity relationships, molecular docking studies at A(2A)AR-based homology models of the A(1) and A(3) ARs and at the A(2A)AR crystal structure were carried out. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.001
• 作为产物：
  描述：

  (E)-3-(2-硝基苯基)丙-2-烯酸乙酯 在 platinum(IV) oxide 氢气 、 溴 、 sodium hydride 作用下， 以 乙醚 、 乙醇 为溶剂， 25.0~100.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 2,5-dihydro-2-methyl-4H-pyrazolo[3,4-c]quinolin-4-one
  参考文献：
  名称：

  Nagarajan, Kuppuswamy; Shah, Rashmi K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 6, p. 316 - 321

  摘要：

  DOI：

文献信息

• Synthesis, structure–affinity relationships, and molecular modeling studies of novel pyrazolo[3,4-c]quinoline derivatives as adenosine receptor antagonists
  作者：Ombretta Lenzi、Vittoria Colotta、Daniela Catarzi、Flavia Varano、Lucia Squarcialupi、Guido Filacchioni、Katia Varani、Fabrizio Vincenzi、Pier Andrea Borea、Diego Dal Ben、Catia Lambertucci、Gloria Cristalli

  DOI：10.1016/j.bmc.2011.05.001

  日期：2011.6

  This paper reports the study of new 2-phenyl- and 2-methylpyrazolo[3,4-c]quinolin-4-ones (series A) and 4-amines (series B), designed as adenosine receptor (AR) antagonists. The synthesized compounds bear at the 6-position various groups, with different lipophilicity and steric hindrance, that were thought to increase human A(1) and A(2A) AR affinities and selectivities, with respect to those of the parent 6-unsubstituted compounds. In series A, this modification was not tolerated since it reduced AR affinity, while in series B it shifted the binding towards the hA(1) subtype. To rationalize the observed structure-affinity relationships, molecular docking studies at A(2A)AR-based homology models of the A(1) and A(3) ARs and at the A(2A)AR crystal structure were carried out. (C) 2011 Elsevier Ltd. All rights reserved.
• Nagarajan, Kuppuswamy; Shah, Rashmi K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 6, p. 316 - 321
  作者：Nagarajan, Kuppuswamy、Shah, Rashmi K.

  DOI：——

  日期：——