N-(2-morpholinoethyl)nicotinamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(2-morpholinoethyl)nicotinamide
• 英文别名: N-β-Morpholinoaethyl-nicotinsaeureamid；N-(2-morpholin-4-yl-ethyl)-nicotinamide；N-(2-morpholin-4-ylethyl)pyridine-3-carboxamide
• 化学式: C₁₂H₁₇N₃O₂
• 分子量: 235.286
• InChiKey: JTNDORAWCIEWNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 烟酰胺 在 Povidone iodine (PVP-I) 作用下， 以 neat (no solvent) 为溶剂， 以98 %的产率得到N-(2-morpholinoethyl)nicotinamide
  参考文献：
  名称：

  实用的聚维酮碘催化伯酰胺和胺的转酰胺基反应

  摘要：

  将无害的聚维酮碘 (PVP-I) 应用于转酰胺基反应，以从各种伯酰胺和胺中获得N-取代的酰胺。在我们开发的方法中应用了多种芳香族、杂环族和脂肪族伯酰胺/胺，在大多数情况下以优异的收率获得了超过 45 种 N-取代的酰胺。成功获得了褪黑激素和依法普西拉等几种药物，其性能优于先前报道的结果。

  DOI：

  10.1016/j.tetlet.2022.154312

文献信息

• Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors
  作者：Lei Shi、Ying Yang、Zi-Lin Li、Zhen-Wei Zhu、Chang-Hong Liu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2009.12.065

  日期：2010.2

  A series of N-(2-morpholinoethyl)nicotinamide (1-13) and N-(3-morpholinopropyl)nicotinamide derivatives (14-26) have been designed, synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. Most of these synthesized compounds proved to be potent, and selective inhibitors of MAO-A rather than of MAO-B. 5-Chloro-6-hydroxy-N-(2-morpholinoethyl)nicotinamide (13) displayed the highest MAO-A inhibitory potency (IC50 = 0.045 mu M) and a good selectivity. 2-Bromo-N-(2-morpholinoethyl)nicotinamide (3) was the most potent MAO-B inhibitor with the IC50 value of 0.32 mu M, but it was not selective. Molecular dockings of compound 13 were performed in order to give structural insights regarding the MAO-A selectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• Practical povidone iodine catalyzed transamidation from primary amides and amines
  作者：Jian Wang、Jiangmeng Ren、Yun-Peng Zhu、Xue-Qin Sun、Peng-Fei Hu、Xin Mu、Bu-Bing Zeng

  DOI：10.1016/j.tetlet.2022.154312

  日期：2023.2

  Non-harmful Povidone iodine (PVP-I) was applied in the transamidation to gain N-substituted amides from various primary amides and amines. Diverse aromatic, heterocyclic and aliphatic primary amides/amines were applied in our developed method and more than 45 N-substituted amides were obtained with excellent yields in most cases. Several drugs such as Melatonin and Efaproxiral were successfully acquired

  将无害的聚维酮碘 (PVP-I) 应用于转酰胺基反应，以从各种伯酰胺和胺中获得N-取代的酰胺。在我们开发的方法中应用了多种芳香族、杂环族和脂肪族伯酰胺/胺，在大多数情况下以优异的收率获得了超过 45 种 N-取代的酰胺。成功获得了褪黑激素和依法普西拉等几种药物，其性能优于先前报道的结果。