Methyl 6,7-bis(methoxymethoxy)-3-methyl-4-oxochromene-2-carboxylate | 1298120-03-2

• 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: Methyl 6,7-bis(methoxymethoxy)-3-methyl-4-oxochromene-2-carboxylate
• CAS: 1298120-03-2
• 化学式: C₁₆H₁₈O₈
• 分子量: 338.314
• InChiKey: RREJLMDHDMTQFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 6,7-bis(methoxymethoxy)-3-methyl-4-oxochromene-2-carboxylate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以94%的产率得到6,7-bis(methoxymethoxy)-3-methyl-4-oxo-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties

  摘要：

  The overactivation of mu-calpain can cause serious cell damage in several diseases. Furthermore, cell death in a number of neurodegenerative disorders is linked to the overproduction of reactive oxygen species. Therefore, antioxidants and mu-calpain inhibitors could have the therapeutic potentials to treat cell death related diseases. New chromone carboxamide derivatives 3 were synthesized to provide alternative mu-calpain inhibitors to compound 2, a conformationally constrained structural variant of MDL 28,170. Compounds 3h and 3l exhibited the most potent p-calpain inhibitory activities (IC50 = 0.09-0.10 mu M), and were comparable to 2 in this respect (IC50 = 0.07 mu M). Compound 31 showed both potent p-calpain inhibitory activity (IC50 = 0.28 mu M) and antioxidant activities in DPPH scavenging and lipid peroxidation inhibition assays. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.025
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 吡啶 、 硫酸 、 三氟化硼乙醚 、 氢溴酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 生成 Methyl 6,7-bis(methoxymethoxy)-3-methyl-4-oxochromene-2-carboxylate
  参考文献：
  名称：

  Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties

  摘要：

  The overactivation of mu-calpain can cause serious cell damage in several diseases. Furthermore, cell death in a number of neurodegenerative disorders is linked to the overproduction of reactive oxygen species. Therefore, antioxidants and mu-calpain inhibitors could have the therapeutic potentials to treat cell death related diseases. New chromone carboxamide derivatives 3 were synthesized to provide alternative mu-calpain inhibitors to compound 2, a conformationally constrained structural variant of MDL 28,170. Compounds 3h and 3l exhibited the most potent p-calpain inhibitory activities (IC50 = 0.09-0.10 mu M), and were comparable to 2 in this respect (IC50 = 0.07 mu M). Compound 31 showed both potent p-calpain inhibitory activity (IC50 = 0.28 mu M) and antioxidant activities in DPPH scavenging and lipid peroxidation inhibition assays. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.025