(2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide | 1253057-39-4

• 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: (2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide
• 英文别名: (E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide
• CAS: 1253057-39-4
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: FJZVGAMGJSVAKT-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-氨基-2-甲基吲哚 、 肉桂酸 在 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以91%的产率得到(2E)-N-(2-methyl-1H-indol-5-yl)-3-phenylprop-2-enamide
  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.