6-chloro-N-(3-morpholinopropyl)nicotinamide | 908544-56-9

• 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: 6-chloro-N-(3-morpholinopropyl)nicotinamide
• 英文别名: 6-chloro-N-(3-morpholin-4-ylpropyl)pyridine-3-carboxamide
• CAS: 908544-56-9
• 化学式: C₁₃H₁₈ClN₃O₂
• mdl: MFCD08587926
• 分子量: 283.758
• InChiKey: CNQVNEPLCSJWDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 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-(3-氨丙基)吗啉 、 6-氯烟酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到6-chloro-N-(3-morpholinopropyl)nicotinamide
  参考文献：
  名称：

  Design of novel nicotinamides as potent and selective monoamine oxidase a inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.12.065

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.