7-((4-isopropylbenzyl)oxy)-2-oxo-2H-chromene-3-carboxylic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-((4-isopropylbenzyl)oxy)-2-oxo-2H-chromene-3-carboxylic acid
• 英文别名: 3-carboxy-7-(4-isopropylbenzyloxy)coumarin；2-Oxo-7-[(4-propan-2-ylphenyl)methoxy]chromene-3-carboxylic acid；2-oxo-7-[(4-propan-2-ylphenyl)methoxy]chromene-3-carboxylic acid
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: JFDAQVNRLYUPDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-((4-isopropylbenzyl)oxy)-2-oxo-2H-chromene-3-carboxylic acid 、 1-(2-aminoethyl)-3-(benzyloxy)-2-methylpyridin-4(1H)-one 在 4-二甲氨基吡啶 、 2-巯基噻唑啉 、 N,N'-二环己基碳二亚胺 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 以80.5%的产率得到N-(2-(3-hydroxy-2-methyl-4-oxopyridin-1(4H)-yl)ethyl)-7-((4-isopropylbenzyl)oxy)-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  具潜在抗AD活性的香豆素杂合吡啶酮酰胺衍 生物及其制备方法与应用

  摘要：

  本发明公开了一种香豆素杂合吡啶酮酰胺衍生物及其制备方法与应用。所述的香豆素杂合吡啶酮酰胺衍生物及其药学上可接受的盐如式(I)或式(II)所示，其可应用于制备抗阿尔兹海默症、抗帕金森病或通过抑制单胺氧化酶、螯合金属铁离子、抗Aβ及抗氧化来治疗的其它疾病或病症药物方面的用途。

  公开号：

  CN110804045B
• 作为产物：
  描述：

  7-羟基香豆素-3-羧酸乙酯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.25h， 生成 7-((4-isopropylbenzyl)oxy)-2-oxo-2H-chromene-3-carboxylic acid
  参考文献：
  名称：

  Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity

  摘要：

  A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multi targeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe(3+) values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-beta(1-42) (A beta(1-42)) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.

  DOI：

  10.1016/j.bmc.2020.115550