(4-methoxy-1-phenyl-1H-indol-2-yl)methanamine | 364629-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (4-methoxy-1-phenyl-1H-indol-2-yl)methanamine
• 英文别名: (4-Methoxy-1-phenylindol-2-yl)methanamine
• CAS: 364629-20-9
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: MSBFXLWNDONIDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酸酐 、 (4-methoxy-1-phenyl-1H-indol-2-yl)methanamine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以90%的产率得到N-[(4-methoxy-1-phenylindol-2-yl)methyl]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：

  4-methoxy-1-phenyl-1H-indol-2-carboxylic acid 在 lithium aluminium tetrahydride 、 氯化亚砜 、 氨 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 (4-methoxy-1-phenyl-1H-indol-2-yl)methanamine
  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.