7-hydroxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid | 104093-05-2

• 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: 7-hydroxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid
• 英文别名: 7-Hydroxy-3-methyl-4-oxo-4H-chromen-2-carbonsaeure；7-Hydroxy-3-methyl-4-oxochromene-2-carboxylic acid
• CAS: 104093-05-2
• 化学式: C₁₁H₈O₅
• 分子量: 220.182
• InChiKey: RODYJCRVYNPXKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3-methyl-4-oxo-4H-chromene-2-carboxylic acid 在 硫酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 N-[(2S,3R)-3-hydroxy-4-[2-(4-methoxyphenyl)ethylamino]-4-oxo-1-phenylbutan-2-yl]-7-(methoxymethoxy)-3-methyl-4-oxochromene-2-carboxamide
  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：

  ethyl 7-methoxy-3-methyl-4-oxo-4H-chromene-2-carboxylate 在 氢溴酸 、 溶剂黄146 作用下， 反应 12.0h， 以51%的产率得到7-hydroxy-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

文献信息

• Clerc-Bory et al., Bulletin de la Societe Chimique de France, 1955, p. 1083,1085
  作者：Clerc-Bory et al.

  DOI：——

  日期：——
• Synthesis of chromone carboxamide derivatives with antioxidative and calpain inhibitory properties
  作者：Sang Hoon Kim、Young Hoon Lee、Seo Yun Jung、Hyoung Ja Kim、Changbae Jin、Yong Sup Lee

  DOI：10.1016/j.ejmech.2011.02.025

  日期：2011.5

  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.