6-benzyloxycarbonylamino-2,5-dihydro-2-phenyl-4H-pyrazolo[3,4-c]quinolin-4-one | 1315307-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-benzyloxycarbonylamino-2,5-dihydro-2-phenyl-4H-pyrazolo[3,4-c]quinolin-4-one
• 英文别名: benzyl N-(4-oxo-2-phenyl-5H-pyrazolo[3,4-c]quinolin-6-yl)carbamate
• CAS: 1315307-76-6
• 化学式: C₂₄H₁₈N₄O₃
• 分子量: 410.432
• InChiKey: UWDRRBDKSISNHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-benzyloxycarbonylamino-2,5-dihydro-2-phenyl-4H-pyrazolo[3,4-c]quinolin-4-one 在 五氯化磷 、 氨 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-phenyl-2H-pyrazolo[3,4-c]quinolin-4,6-diamine
  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：

  (1H-indol-7-yl)carbamic acid benzyl ester 在 吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 生成 6-benzyloxycarbonylamino-2,5-dihydro-2-phenyl-4H-pyrazolo[3,4-c]quinolin-4-one
  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