N-[2-(5-甲氧基-1H-吲哚-3-基)乙基]吡啶-3-甲酰胺 | 29745-42-4

• 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
• 中文名称: N-[2-(5-甲氧基-1H-吲哚-3-基)乙基]吡啶-3-甲酰胺
• 英文名称: N-[2-(methoxy-1H-indol-3-yl)ethyl]nicotinamide
• 英文别名: N-[2-(5-methoxy-indol-3-yl)-ethyl]-nicotinamide；Nicotinamide, N-(2-(5-methoxyindol-3-yl)ethyl)-；N-[2-(5-methoxy-1H-indol-3-yl)ethyl]pyridine-3-carboxamide
• CAS: 29745-42-4
• 化学式: C₁₇H₁₇N₃O₂
• mdl: MFCD01711817
• 分子量: 295.341
• InChiKey: JAXFNBSXSXDREO-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  612.5±50.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-[2-(5-甲氧基-1H-吲哚-3-基)乙基]吡啶-3-甲酰胺 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(5-methoxy-1H-indol-3-yl)-N-(pyridin-3-ylmethyl)ethanamine
  参考文献：
  名称：

  Optimization of a pharmacophore model for 5-HT4 agonists using CoMFA and receptor based alignment

  摘要：

  Twenty two 5-HT4 agonists obtained from our laboratory and the recent literature were used to develop a CoMFA model to predict 5-HT4 agonist activity. Two models were produced and compared for predictivity, the first by alignments based on atom overlapping (model A) and the second by adding agonist binding site interacting points of the 5-HT4 receptor (model B). Comparison of the two models showed that the q(2) value for model A was 0.564 vs. 0.582 for model B. Model B indicated that the predictive power model stems from far lower steric contributions, 0.270 compared to model A's 0.502. The dominant defining features were the electrostatic contributions for model B, 0.664 up from 0.477 in model A. The contributions from the LogP factor were minimal, 0.085 in both models. The synthesized compounds showed agonist activity at mu mol level. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.017
• 作为产物：
  描述：

  5-甲氧基色胺 、 氯化烟碱盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到N-[2-(5-甲氧基-1H-吲哚-3-基)乙基]吡啶-3-甲酰胺
  参考文献：
  名称：

  Synthesis, Testing and Structure-Activity Studies on a Library of 5-HT4 Ligands

  摘要：

  设计、合成并测试了几种吲哚衍生物及其类似物，这些化合物属于一系列相关的结构类别，作为 5-HT4 受体的配体。在每个系列中，结合实验显示具有良好亲和力的化合物在 1 µM 浓度下表现出高百分比的置换值。其中最有效的化合物（20）的 pKi 值为 8.54，显示出非常好的亲和力。这些吲哚类似物与之前在我们实验室合成的 55 种配体相结合，以探索这些 5-HT4 配体的结构-活性关系。通过比较分子场分析（CoMFA），从早期简单的药效团模型延伸出两个新的分子特征，超越了主要的氨基结合位点。该药效团确认了一种新描述的四氢喹啉类似物能够匹配模型的基本要求，并且该分子的药理学特性有更详细的说明。

  DOI：

  10.2174/157340610793563965

文献信息

• Optimization of a pharmacophore model for 5-HT4 agonists using CoMFA and receptor based alignment
  作者：M ISKANDER、L LEUNG、T BULEY、F AYAD、J DIIULIO、Y TAN、I COUPAR

  DOI：10.1016/j.ejmech.2005.07.017

  日期：2006.1

  Twenty two 5-HT4 agonists obtained from our laboratory and the recent literature were used to develop a CoMFA model to predict 5-HT4 agonist activity. Two models were produced and compared for predictivity, the first by alignments based on atom overlapping (model A) and the second by adding agonist binding site interacting points of the 5-HT4 receptor (model B). Comparison of the two models showed that the q(2) value for model A was 0.564 vs. 0.582 for model B. Model B indicated that the predictive power model stems from far lower steric contributions, 0.270 compared to model A's 0.502. The dominant defining features were the electrostatic contributions for model B, 0.664 up from 0.477 in model A. The contributions from the LogP factor were minimal, 0.085 in both models. The synthesized compounds showed agonist activity at mu mol level. (c) 2005 Elsevier SAS. All rights reserved.
• Synthesis, Testing and Structure-Activity Studies on a Library of 5-HT4 Ligands
  作者：Amir Hanna-Elias、David T. Manallack、Alla Levit、William Nguyen、Fadi Ayad、Glen Perera、Marina Shapiro、Helen R. Irving、Ian M. Coupar、Magdy N. Iskander

  DOI：10.2174/157340610793563965

  日期：2010.11.1

  Several indole derivatives and analogues comprising a range of related structural classes were designed, synthesized and tested as ligands for the 5-HT4 receptor. Within each series, binding experiments showed compounds with good affinity demonstrating high percentage displacement values at 1 µM. The most potent of these (20) had a pKi of 8.54 demonstrating very good affinity. These indole analogues were combined with 55 ligands that were previously produced in our laboratory to explore the structure-activity relationships of these 5-HT4 ligands. A CoMFA (Comparative Molecular Field Analysis) analysis was used to extend an earlier simple pharmacophore to suggest two new molecular features beyond the primary amino binding site. The pharmacophore confirmed that a newly described tetrahydroquinoline analogue was able to match the basic requirements of the model and the pharmacology of this molecule is provided in more detail.

  设计、合成并测试了几种吲哚衍生物及其类似物，这些化合物属于一系列相关的结构类别，作为 5-HT4 受体的配体。在每个系列中，结合实验显示具有良好亲和力的化合物在 1 µM 浓度下表现出高百分比的置换值。其中最有效的化合物（20）的 pKi 值为 8.54，显示出非常好的亲和力。这些吲哚类似物与之前在我们实验室合成的 55 种配体相结合，以探索这些 5-HT4 配体的结构-活性关系。通过比较分子场分析（CoMFA），从早期简单的药效团模型延伸出两个新的分子特征，超越了主要的氨基结合位点。该药效团确认了一种新描述的四氢喹啉类似物能够匹配模型的基本要求，并且该分子的药理学特性有更详细的说明。