(E)-3-(4-methoxy-1-phenyl-1H-indol-2-yl)propenenitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (E)-3-(4-methoxy-1-phenyl-1H-indol-2-yl)propenenitrile
• 英文别名: (E)-3-(4-methoxy-1-phenylindol-2-yl)prop-2-enenitrile
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: ZERMVIZCXROZJZ-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酸酐 、 (E)-3-(4-methoxy-1-phenyl-1H-indol-2-yl)propenenitrile 在 镍 氢气 作用下， 以 四氢呋喃 为溶剂， 50.0 ℃ 、405.33 kPa 条件下， 反应 6.0h， 以79%的产率得到N-[3-(4-methoxy-1-phenylindol-2-yl)propyl]propanamide
  参考文献：
  名称：

  2-N-Acylaminoalkylindoles:  Design and Quantitative Structure−Activity Relationship Studies Leading to MT₂-Selective Melatonin Antagonists

  摘要：

  Several indole analogues of melatonin (MLT) were obtained by moving the MLT side chain from C-3 to C-2 of the indole ring. Binding and in vitro functional assays were performed on cloned human MT1 and MT2 receptors, stably transfected in NIH3T3 cells. Quantitative structure-activity relationship studies showed that 4-methoxy-2-(N-acylaminomethyl)indoles, with a benzyl group in position 1, were selective MT2 antagonists and, in particular, N-[(1-p-chlorobenzyl-4-methoxy-1H-indol-2-yl)methyl]propanamide (12) behaved as a pure antagonist at MT1 and MT2 receptors, with a 148-fold selectivity for MT2. We present a topographical model that suggests a lipophilic group, located out of the plane of the indole ring of MLT, as the key feature of the MT2 selective antagonists.

  DOI：

  10.1021/jm001125h
• 作为产物：
  描述：

  氰甲基三苯基氯化磷 、 4-methoxy-1-phenyl-1H-indole-2-carboxaldehyde 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以74%的产率得到(E)-3-(4-methoxy-1-phenyl-1H-indol-2-yl)propenenitrile
  参考文献：
  名称：

  2-N-Acylaminoalkylindoles:  Design and Quantitative Structure−Activity Relationship Studies Leading to MT₂-Selective Melatonin Antagonists

  摘要：

  Several indole analogues of melatonin (MLT) were obtained by moving the MLT side chain from C-3 to C-2 of the indole ring. Binding and in vitro functional assays were performed on cloned human MT1 and MT2 receptors, stably transfected in NIH3T3 cells. Quantitative structure-activity relationship studies showed that 4-methoxy-2-(N-acylaminomethyl)indoles, with a benzyl group in position 1, were selective MT2 antagonists and, in particular, N-[(1-p-chlorobenzyl-4-methoxy-1H-indol-2-yl)methyl]propanamide (12) behaved as a pure antagonist at MT1 and MT2 receptors, with a 148-fold selectivity for MT2. We present a topographical model that suggests a lipophilic group, located out of the plane of the indole ring of MLT, as the key feature of the MT2 selective antagonists.

  DOI：

  10.1021/jm001125h

文献信息

• 2-<i>N</i>-Acylaminoalkylindoles:  Design and Quantitative Structure−Activity Relationship Studies Leading to MT₂-Selective Melatonin Antagonists
  作者：Gilberto Spadoni、Cesarino Balsamini、Giuseppe Diamantini、Andrea Tontini、Giorgio Tarzia、Marco Mor、Silvia Rivara、Pier Vincenzo Plazzi、Romolo Nonno、Valeria Lucini、Marilou Pannacci、Franco Fraschini、Bojidar Michaylov Stankov

  DOI：10.1021/jm001125h

  日期：2001.8.1

  Several indole analogues of melatonin (MLT) were obtained by moving the MLT side chain from C-3 to C-2 of the indole ring. Binding and in vitro functional assays were performed on cloned human MT1 and MT2 receptors, stably transfected in NIH3T3 cells. Quantitative structure-activity relationship studies showed that 4-methoxy-2-(N-acylaminomethyl)indoles, with a benzyl group in position 1, were selective MT2 antagonists and, in particular, N-[(1-p-chlorobenzyl-4-methoxy-1H-indol-2-yl)methyl]propanamide (12) behaved as a pure antagonist at MT1 and MT2 receptors, with a 148-fold selectivity for MT2. We present a topographical model that suggests a lipophilic group, located out of the plane of the indole ring of MLT, as the key feature of the MT2 selective antagonists.