diethyl 2-methyl-3-(phenylamino)maleate | 59946-31-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-methyl-3-(phenylamino)maleate
• CAS: 59946-31-5
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: BUIOUXGAPUYUCI-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-methyl-3-(phenylamino)maleate 在 mineral oil 作用下， 以39%的产率得到4-hydroxy-3-methylquinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of 4-quinolinone 2-carboxamides as calpain inhibitors

  摘要：

  Calpains are involved in a variety of calcium-regulated cellular processes, such as signal transduction, cell proliferation, differentiation, and apoptosis. Excessive calpain activation contributes to serious cellular damage and has been reported in many pathological conditions. 4-Quinolinone 2-carboxamide derivatives were prepared and evaluated for mu-calpain inhibitory activities. Of the compounds synthesized, 3a and 3k, which possess a primary amide and 4-methoxyphenethyl amide at P-1' region, were found to most potently inhibit mu-calpain with IC50 values of 0.71 +/- 0.07 and 0.73 +/- 0.23 mu M, respectively. On the other hand, the incorporation of pyridine-containing amides decreased inhibitory activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.097
• 作为产物：
  描述：

  草酰丙酸二乙酯 、 苯胺 在 溶剂黄146 作用下， 以77%的产率得到diethyl 2-methyl-3-(phenylamino)maleate
  参考文献：
  名称：

  Design and synthesis of 4-quinolinone 2-carboxamides as calpain inhibitors

  摘要：

  Calpains are involved in a variety of calcium-regulated cellular processes, such as signal transduction, cell proliferation, differentiation, and apoptosis. Excessive calpain activation contributes to serious cellular damage and has been reported in many pathological conditions. 4-Quinolinone 2-carboxamide derivatives were prepared and evaluated for mu-calpain inhibitory activities. Of the compounds synthesized, 3a and 3k, which possess a primary amide and 4-methoxyphenethyl amide at P-1' region, were found to most potently inhibit mu-calpain with IC50 values of 0.71 +/- 0.07 and 0.73 +/- 0.23 mu M, respectively. On the other hand, the incorporation of pyridine-containing amides decreased inhibitory activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.097