(4-methoxy-1-phenyl-1H-indol-2-yl)methanol | 213682-12-3

• 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)methanol
• 英文别名: (4-Methoxy-1-phenylindol-2-yl)methanol
• CAS: 213682-12-3
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: KXHXWQKGWBPDHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  34.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-methoxy-1-phenyl-1H-indol-2-yl)methanol 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 2-(4-methoxy-1-phenyl-1H-indol-2-yl)ethylamine
  参考文献：
  名称：

  2-[N-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists

  摘要：

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.

  DOI：

  10.1021/jm970721h
• 作为产物：
  描述：

  4-甲氧吲哚-2-羧酸甲脂 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 potassium carbonate 、 zinc(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 6.75h， 生成 (4-methoxy-1-phenyl-1H-indol-2-yl)methanol
  参考文献：
  名称：

  2-[N-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists

  摘要：

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.

  DOI：

  10.1021/jm970721h

文献信息

• 2-[<i>N</i>-Acylamino(C₁−C₃)alkyl]indoles as MT₁ Melatonin Receptor Partial Agonists, Antagonists, and Putative Inverse Agonists
  作者：Gilberto Spadoni、Cesarino Balsamini、Annalida Bedini、Giuseppe Diamantini、Barbara Di Giacomo、Andrea Tontini、Giorgio Tarzia、Marco Mor、Pier Vincenzo Plazzi、Silvia Rivara、Romolo Nonno、Marilou Pannacci、Valeria Lucini、Franco Fraschini、Bojidar Michaylov Stankov

  DOI：10.1021/jm970721h

  日期：1998.9.1

  The synthesis of several novel indole melatonin analogues substituted at the 2-position with acylaminomethyl (8-11), acylaminoethyl (5a-k), or acylaminopropyl (13) side chains is reported. On the basis of a novel in vitro functional assay (specific binding of [S-35]GTP gamma S), which can discriminate agonist from partial agonist, antagonist, and inverse agonist ligands, Ba,g,h,j and 13 were shown to be partial agonists, 5d,e and 8-11 competitive antagonists, and 5b,c,k putative inverse agonists. Binding and functional assays were performed on cloned human MT1 receptor. Structure-activity relationship considerations indicate that N-[1-aryl-2-(4-methoxy-1H-indol-2-yl)(C-1-C-2)alkyl]alkanamides represent a lead structure for this type of ligands.