(E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester | 1253057-49-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
• 英文别名: (E)-Cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-ylester；(2-oxo-3H-1-benzofuran-5-yl) (E)-3-phenylprop-2-enoate
• CAS: 1253057-49-6
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: LNAJHFBURMAQSH-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯基乙酸GAMMA内酯 、 肉桂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.08h， 以50%的产率得到(E)-cinnamic acid 2-oxo-2,3-dihydro-benzofuran-5-yl ester
  参考文献：
  名称：

  Inhibition of monoamine oxidase by indole and benzofuran derivatives

  摘要：

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. A series of indole and benzofuran derivatives were synthesised and evaluated as inhibitors of the two MAO isoforms, MAO-A and MAO-B. In general, the derivatives were found to be selective MAO-B inhibitors with K(1) values in the nanoMolar (nM) to microMolar (mu M) concentration range. The most potent MAO-B inhibitor, 3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide, exhibited a K, value of 0 03 mu M and was 99 fold more selective for the B isoform. We conclude that these indole and benzofuran derivatives are promising reversible MAO-B inhibitors with a possible role in the treatment of neurodegenerative diseases such as Parkinson's disease (PD). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.005

文献信息

• Inhibition of monoamine oxidase by indole and benzofuran derivatives
  作者：Louis H.A. Prins、Jacobus P. Petzer、Sarel F. Malan

  DOI：10.1016/j.ejmech.2010.07.005

  日期：2010.10

  Monoamine oxidase (MAO) is an important drug target for the treatment of neurological disorders. A series of indole and benzofuran derivatives were synthesised and evaluated as inhibitors of the two MAO isoforms, MAO-A and MAO-B. In general, the derivatives were found to be selective MAO-B inhibitors with K(1) values in the nanoMolar (nM) to microMolar (mu M) concentration range. The most potent MAO-B inhibitor, 3,4-dichloro-N-(2-methyl-1H-indol-5-yl)benzamide, exhibited a K, value of 0 03 mu M and was 99 fold more selective for the B isoform. We conclude that these indole and benzofuran derivatives are promising reversible MAO-B inhibitors with a possible role in the treatment of neurodegenerative diseases such as Parkinson's disease (PD). (C) 2010 Elsevier Masson SAS. All rights reserved.