N-(3-morpholinopropyl)nicotinamide | 313988-81-7

• 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-(3-morpholinopropyl)nicotinamide
• 英文别名: N-(3-morpholin-4-ylpropyl)pyridine-3-carboxamide
• CAS: 313988-81-7
• 化学式: C₁₃H₁₉N₃O₂
• 分子量: 249.313
• InChiKey: WKRCSVLEBALYIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C
• 沸点：
  481.9±35.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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 、 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86%的产率得到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

• [EN] NOVEL 3-(2-AMINO-6-PYRIDINYL)-4-HYDROXYPHENYL AMINE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE 3-(2-AMINO-6-PYRIDINYL)-4-HYDROXYPHÉNYLAMINE
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2006068410A1

  公开（公告）日：2006-06-29

  [EN] The present invention relates to novel compounds having 3-(2-amino-6-pyrimidinyl)-4-hydroxyphenyl amine structure, as being illustrated in Formula 1, and preparations for preparation of them, and the use of them, and pharmaceutical compositions containing them at a therapeutically effective amount. The compounds according to the present invention are useful for the treatment and prevention of diseases resulting from the undesired KDR activity, for example, angiogenesis-related diseases such as cancers, psoriasis, rheumatoid arthritis, diabetic retinopathy, etc.
  [FR] La présente invention concerne de nouveaux composés de structure 3-(2-amino-6-pyrimidinyl)-4-hydroxyphénylamine, tels qu'illustrés par la Formule 1, ainsi que leurs méthodes de synthèse, leurs applications, et des préparations pharmaceutiques contenant lesdits composés à des teneurs thérapeutiques. Les composés selon la présente invention peuvent être employés dans le traitement prophylactique et thérapeutique de maladies dues à une activité anormale de KDR, par exemple des maladies de type angiogenèse telles que les cancers, le psoriasis, la polyarthrite rhumatoïde, la rétinopathie diabétique, etc.
• 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.