N-(2-(4-methoxy-1H-indol-3-yl)ethyl)acetamide | 109021-55-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-(4-methoxy-1H-indol-3-yl)ethyl)acetamide
• 英文别名: N-acetyl-4-methoxytryptamine；N-[2-(4-methoxy-1H-indol-3-yl)ethyl]acetamide
• CAS: 109021-55-8
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: ZXGPNCSIPFYCDA-UHFFFAOYSA-N

物化性质

• 沸点：
  512.8±40.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-(4-methoxy-1H-indol-3-yl)ethyl)acetamide 在 氢氧化钾 、 sodium hydroxide 、 potassium permanganate 、 18-冠醚-6 、 phosphorus pentoxide 作用下， 以 吡啶 、 甲醇 、 乙醇 、 xylene 、 苯 为溶剂， 反应 42.0h， 生成 4-甲氧基色胺
  参考文献：
  名称：

  Yamada, Fumio; Saida, Yoshihiro; Somei, Masanori, Heterocycles, 1986, vol. 24, # 9, p. 2619 - 2627

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基吲哚 在 lithium aluminium tetrahydride 、 TEA 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 11.5h， 生成 N-(2-(4-methoxy-1H-indol-3-yl)ethyl)acetamide
  参考文献：
  名称：

  Melatonin Receptor Ligands:  Synthesis of New Melatonin Derivatives and Comprehensive Comparative Molecular Field Analysis (CoMFA) Study

  摘要：

  The CoMFA methodology was applied to melatonin receptor ligands in order to establish quantitative structure-affinity relationships. One hundred thirty-three compounds were considered: they were either collected from literature or newly synthesized in order to gain information about the less explored positions. To this end, various melatonin derivatives were prepared and their affinity for quail optic tecta melatonin receptor was tested. Compounds were aligned on the putative active conformation of melatonin proposed by our previously reported pharmacophore search, and their relative affinities were calculated from the displacement of 2-[I-125]-iodomelatonin on different tissues expressing aMT receptors. Compounds were grouped into three sets according to their topology. Subset A: melatonin-like compounds; subset B: N-acyl-2-amino-8-methoxytetralins and related compounds; subset C: N-acyl-phenylalkylamines and related compounds. CoMFA models were derived for each set, using the steric, electrostatic, and lipophilic fields as structural descriptors; the PLS analyses were characterized by good statistical parameters, taking into account the heterogeneity of the binding data, obtained with different experimental protocols. From the CoMFA model for the melatonin-like compounds, besides the well-known positive effect of 2-substitution, a low steric tolerance for substituents in 1, 6, and 7, and a negative effect of electron-rich 4-substituents were observed; the information provided by the newly synthesized compounds was essential for these results. Moreover, a comprehensive model for the 133 compounds, accounting for a common alignment and a common mode of interaction at the melatonin receptor, was derived (Q(2) = 0.769, R-2 = 0.905). This model validates our previously reported pharmacophore search and offers a clear depiction of the structure-affinity relationships for the melatonin receptor ligands.

  DOI：

  10.1021/jm9810093

文献信息

• Iridium-Catalyzed Direct Synthesis of Tryptamine Derivatives from Indoles: Exploiting N-Protected β-Amino Alcohols as Alkylating Agents
  作者：Silvia Bartolucci、Michele Mari、Annalida Bedini、Giovanni Piersanti、Gilberto Spadoni

  DOI：10.1021/acs.joc.5b00195

  日期：2015.3.20

  The selective C3-alkylation of indoles with N-protected ethanolamines involving the “borrowing hydrogen” strategy is described. This method provides convenient and sustainable access to several tryptamine derivatives.

  描述了涉及“借用氢”策略的N-保护的乙醇胺对吲哚的选择性C3-烷基化反应。该方法提供了对几种色胺衍生物的方便且可持续的获取途径。
• Melatonin Receptor Ligands:  Synthesis of New Melatonin Derivatives and Comprehensive Comparative Molecular Field Analysis (CoMFA) Study
  作者：Marco Mor、Silvia Rivara、Claudia Silva、Fabrizio Bordi、Pier Vincenzo Plazzi、Gilberto Spadoni、Giuseppe Diamantini、Cesarino Balsamini、Giorgio Tarzia、Franco Fraschini、Valeria Lucini、Romolo Nonno、Bojidar Michaylov Stankov

  DOI：10.1021/jm9810093

  日期：1998.9.1

  The CoMFA methodology was applied to melatonin receptor ligands in order to establish quantitative structure-affinity relationships. One hundred thirty-three compounds were considered: they were either collected from literature or newly synthesized in order to gain information about the less explored positions. To this end, various melatonin derivatives were prepared and their affinity for quail optic tecta melatonin receptor was tested. Compounds were aligned on the putative active conformation of melatonin proposed by our previously reported pharmacophore search, and their relative affinities were calculated from the displacement of 2-[I-125]-iodomelatonin on different tissues expressing aMT receptors. Compounds were grouped into three sets according to their topology. Subset A: melatonin-like compounds; subset B: N-acyl-2-amino-8-methoxytetralins and related compounds; subset C: N-acyl-phenylalkylamines and related compounds. CoMFA models were derived for each set, using the steric, electrostatic, and lipophilic fields as structural descriptors; the PLS analyses were characterized by good statistical parameters, taking into account the heterogeneity of the binding data, obtained with different experimental protocols. From the CoMFA model for the melatonin-like compounds, besides the well-known positive effect of 2-substitution, a low steric tolerance for substituents in 1, 6, and 7, and a negative effect of electron-rich 4-substituents were observed; the information provided by the newly synthesized compounds was essential for these results. Moreover, a comprehensive model for the 133 compounds, accounting for a common alignment and a common mode of interaction at the melatonin receptor, was derived (Q(2) = 0.769, R-2 = 0.905). This model validates our previously reported pharmacophore search and offers a clear depiction of the structure-affinity relationships for the melatonin receptor ligands.
• Yamada, Fumio; Saida, Yoshihiro; Somei, Masanori, Heterocycles, 1986, vol. 24, # 9, p. 2619 - 2627
  作者：Yamada, Fumio、Saida, Yoshihiro、Somei, Masanori

  DOI：——

  日期：——