ethyl (7-benzyloxy-1H-indol-3-yl)glyoxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl (7-benzyloxy-1H-indol-3-yl)glyoxylate
• 英文别名: ethyl 7-(phenylmethoxy)-indol-3-yl-glyoxylate；ethyl 2-oxo-2-(7-phenylmethoxy-1H-indol-3-yl)acetate
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: GFARFDRNGAHQAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (7-benzyloxy-1H-indol-3-yl)glyoxylate 在 五氯化磷 、 palladium 10% on activated carbon 、 氨 、 氢气 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 120.0 ℃ 、241.32 kPa 条件下， 反应 51.0h， 生成 6-phenethoxy-2-phenyl-2H-pyrazolo[3,4-c]quinolin-4-amine
  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：

  7-苄氧基吲哚 、 草酰氯单乙酯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以77%的产率得到ethyl (7-benzyloxy-1H-indol-3-yl)glyoxylate
  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

文献信息

• Substituted 1,3,4,9-tetrahydropyrano[3,4,-b]indole-1-acetic acids,
  申请人：American Home Products Corporation

  公开号：US04810699A1

  公开（公告）日：1989-03-07

  Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1,5, 6, 7 and 8. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation and use are also disclosed.

  吲哚衍生物的特征是具有1,3,4,9-四氢吡喃[3,4-b]吲哚-1-乙酸核，该核带有在位置1、5、6、7和8处的取代基。这些衍生物是有用的抗炎和镇痛剂，并且还公开了它们的制备和使用方法。
• US4810699A
  申请人：——

  公开号：US4810699A

  公开（公告）日：1989-03-07
• 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.