2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide | 189884-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide
• CAS: 189884-58-0
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: HJOUNQSRBQMHEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  451.2±55.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide 在 lithium aluminium tetrahydride 作用下， 生成 2-(5-甲氧基-2-甲基-1H-吲哚-3-基)-N,N-二甲基乙胺
  参考文献：
  名称：

  Characterization of the 5-HT₇ Receptor. Determination of the Pharmacophore for 5-HT₇ Receptor Agonism and CoMFA-Based Modeling of the Agonist Binding Site

  摘要：

  On the basis of a set of 20 diverse 5-HT7 receptor agonists, the pharmacophore for 5-HT7 receptor agonism was determined. Additionally two CoMFA models were developed, based on different alignments of the agonists. Both models show good correlations between experimental and predictive pK(i) values and show a high degree of similarity. The CoMFA fields were subsequently used to map the agonist binding site of the model of the 5-HT7 receptor. Important roles in ligand binding are attributed to Asp162 of TM3 (interaction with a protonated nitrogen), and Thr244 of TM5 (interaction with a substituent at an aromatic moiety). Amino acid residues of the aromatic cluster of TM6 are hypothesized to play an important role in ligand binding as pi-pi stacking moieties. Agonists missing a hydrogen-bond-accepting moiety, but possessing an aromatic substituent instead, seem to bind the receptor with high affinity as well by occupying a lipophilic pocket hosted by residues of TM5 and TM6.

  DOI：

  10.1021/jm030826m
• 作为产物：
  描述：

  5-甲氧基-2-甲基吲哚 以 乙醚 、 氯仿 、 水 为溶剂， 生成 2-(5-Methoxy-2-methyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide
  参考文献：
  名称：

  Characterization of the 5-HT₇ Receptor. Determination of the Pharmacophore for 5-HT₇ Receptor Agonism and CoMFA-Based Modeling of the Agonist Binding Site

  摘要：

  On the basis of a set of 20 diverse 5-HT7 receptor agonists, the pharmacophore for 5-HT7 receptor agonism was determined. Additionally two CoMFA models were developed, based on different alignments of the agonists. Both models show good correlations between experimental and predictive pK(i) values and show a high degree of similarity. The CoMFA fields were subsequently used to map the agonist binding site of the model of the 5-HT7 receptor. Important roles in ligand binding are attributed to Asp162 of TM3 (interaction with a protonated nitrogen), and Thr244 of TM5 (interaction with a substituent at an aromatic moiety). Amino acid residues of the aromatic cluster of TM6 are hypothesized to play an important role in ligand binding as pi-pi stacking moieties. Agonists missing a hydrogen-bond-accepting moiety, but possessing an aromatic substituent instead, seem to bind the receptor with high affinity as well by occupying a lipophilic pocket hosted by residues of TM5 and TM6.

  DOI：

  10.1021/jm030826m

文献信息

• Konformation und Rotationsbarrieren substituierter Glyoxylsäureamide
  作者：Martina Spaeth、Peter Plischka、Frank-Michael Bohnen、Regine Herbst-Irmer、Hartmut Laatsch

  DOI：10.1002/prac.19973390143

  日期：——

  Semiempirical calculations predict an orthogonal orientation of the carbonyl groups in tertiary glyoxylic acid amides, which is in good agreement with an X-ray structure analysis of 5. Due to the influence of the a-carbonyl group, the rotation barrier in the substituted glyoxylic acid amides 2a-d, 3a, 3b, and 4-6 (Delta G(c)(#)=84-92 kJ mol(-1)) is about 10 kJ/mol higher than in simple acid amides, as was found by dynamic NMR line shape analysis.