N-(3-morpholinopropyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide | 325779-24-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(3-morpholinopropyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(3-morpholin-4-ylpropyl)-6-nitro-2-oxochromene-3-carboxamide
• CAS: 325779-24-6
• 化学式: C₁₇H₁₉N₃O₆
• 分子量: 361.354
• InChiKey: JDELIZJINUNKNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-(羟基(氧代)氨基)-2-氧代-2H-苯并吡喃-3-羧酸乙酯 在 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 N-(3-morpholinopropyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO

  摘要：

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.

  DOI：

  10.1016/j.ejmech.2014.04.060

文献信息

• Design, Synthesis, and Cholinesterase Inhibition Assay of Coumarin‐3‐carboxamide‐ <i>N</i> ‐morpholine Hybrids as New Anti‐Alzheimer Agents
  作者：Maliheh Barazandeh Tehrani、Zahra Rezaei、Mehdi Asadi、Hossein Behnammanesh、Hamid Nadri、Fatemeh Afsharirad、Alireza Moradi、Bagher Larijani、Maryam Mohammadi‐Khanaposhtani、Mohammad Mahdavi

  DOI：10.1002/cbdv.201900144

  日期：2019.7

  Among them, propylmorpholine derivative 5g (N-[3-(morpholin-4-yl)propyl]-2-oxo-2H-chromene-3-carboxamide) bearing an unsubstituted coumarin moiety and ethylmorpholine derivative 5d (6-bromo-N-[2-(morpholin-4-yl)ethyl]-2-oxo-2H-chromene-3-carboxamide) bearing a 6-bromocoumarin moiety showed the most activity against AChE and BuChE, respectively. The inhibitory activity of compound 5g against AChE was

  设计并合成了一系列新的香豆素-3-羧酰胺-N-吗啉杂化物5a-5l作为胆碱酯酶抑制剂。标题化合物的合成方法始于2-羟基苯甲醛衍生物与Meldrum's酸的反应，得到相应的香豆素3-羧酸。然后，将后面的化合物与2-吗啉代乙胺或N-（3-氨基丙基）吗啉酰胺化导致形成化合物5a-5l。对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的体外抑制筛选显示，大多数合成的化合物具有有效的AChE抑制作用，而它们的BuChE抑制作用为中度至弱。其中，带有未取代香豆素部分的丙基吗啉衍生物5g（N- [3-（吗啉-4-基）丙基] -2-氧代-2H-色烯-3-羧酰胺）和乙基吗啉衍生物5d（6-溴-N- [2-带有6-溴香豆素部分的（吗啉-4-基）乙基] -2-氧代-2H-亚甲基-3-羧酰胺分别显示出对AChE和BuChE的最大活性。化合物5g对AChE的抑制活性是rivastigmine的1.78倍，化合
• New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO
  作者：Zhi-Xiang Pan、Xu He、Yan-Yan Chen、Wen-Jian Tang、Jing-Bo Shi、Yu-Lan Tang、Bao-An Song、Jun Li、Xin-Hua Liu

  DOI：10.1016/j.ejmech.2014.04.060

  日期：2014.6

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.