3-Methyl-4-oxo-4H-chromene-2-carboxylic acid [(1S,2R)-1-benzyl-2-hydroxy-2-(2-morpholin-4-yl-ethylcarbamoyl)-ethyl]-amide | 859403-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Methyl-4-oxo-4H-chromene-2-carboxylic acid [(1S,2R)-1-benzyl-2-hydroxy-2-(2-morpholin-4-yl-ethylcarbamoyl)-ethyl]-amide
• 英文别名: N-[(2S,3R)-3-hydroxy-4-(2-morpholin-4-ylethylamino)-4-oxo-1-phenylbutan-2-yl]-3-methyl-4-oxochromene-2-carboxamide
• CAS: 859403-97-7
• 化学式: C₂₇H₃₁N₃O₆
• 分子量: 493.56
• InChiKey: GLRJCIWMASBYDZ-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Methyl-4-oxo-4H-chromene-2-carboxylic acid [(1S,2R)-1-benzyl-2-hydroxy-2-(2-morpholin-4-yl-ethylcarbamoyl)-ethyl]-amide 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-Methyl-4-oxo-4H-chromene-2-carboxylic acid [(S)-1-benzyl-2-(2-morpholin-4-yl-ethylcarbamoyl)-2-oxo-ethyl]-amide
  参考文献：
  名称：

  Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors

  摘要：

  Excessive calpain activations contribute to serious cellular damage and have been found in many pathological conditions. Novel chromone carboxamides derived from ketoamides were prepared and evaluated for mu-calpain inhibition. Among synthesized, compound 2i was the most potent calpain inhibitor with an IC50 value of 0.24 +/- 0.11 mu M comparable to the activity of peptide aldehyde calpain inhibitor MDL 28,170. Furthermore, compound 2i showed higher selectivity for mu-calpain over two related cysteine proteases cathepsin B and cathepsin L, suggesting the chromone ring as a good scaffold for selective mu-calpain inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.095
• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 在 palladium dihydroxide 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 3-Methyl-4-oxo-4H-chromene-2-carboxylic acid [(1S,2R)-1-benzyl-2-hydroxy-2-(2-morpholin-4-yl-ethylcarbamoyl)-ethyl]-amide
  参考文献：
  名称：

  Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors

  摘要：

  Excessive calpain activations contribute to serious cellular damage and have been found in many pathological conditions. Novel chromone carboxamides derived from ketoamides were prepared and evaluated for mu-calpain inhibition. Among synthesized, compound 2i was the most potent calpain inhibitor with an IC50 value of 0.24 +/- 0.11 mu M comparable to the activity of peptide aldehyde calpain inhibitor MDL 28,170. Furthermore, compound 2i showed higher selectivity for mu-calpain over two related cysteine proteases cathepsin B and cathepsin L, suggesting the chromone ring as a good scaffold for selective mu-calpain inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.095