2-[5-(tetrahydropyran-2-yloxy)pentyl]chroman-4-one | 1026724-86-6

• 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: 2-[5-(tetrahydropyran-2-yloxy)pentyl]chroman-4-one
• 英文别名: 2-[5-(Oxan-2-yloxy)pentyl]-2,3-dihydrochromen-4-one
• CAS: 1026724-86-6
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: KUTMAQFCIOGTPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[5-(tetrahydropyran-2-yloxy)pentyl]chroman-4-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 2-(5-hydroxypentyl)chroman-4-one
  参考文献：
  名称：

  Design, Synthesis, and Physicochemical and Biological Characterization of a New Iron Chelator of the Family of Hydroxychromenes

  摘要：

  Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalized from specific carriers or intracellular sites (inflammation, neurodegenerative diseases, postischaemic reperfusion, xenobiotic intoxications, etc.), In the present work we appropriately modified an iron chelator of the hydroxychromene family in, order to obtain a tridentate chelator that would inactivate the iron redox cycle after its complexation, with a view to using this molecule in human therapy and/or in disease prevention. We synthesized such a chelator for the first time and show, by different physticochemical analysis, its tridentate nature and, importantly, its capacity to chelate iron with enough strength to inhibit both iron-dependent H2O2 generation and lipid peroxidation in in vitro biological systems.

  DOI：

  10.1021/jm021022u
• 作为产物：
  描述：

  6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 在 四氢吡咯 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-[5-(tetrahydropyran-2-yloxy)pentyl]chroman-4-one
  参考文献：
  名称：

  Design, Synthesis, and Physicochemical and Biological Characterization of a New Iron Chelator of the Family of Hydroxychromenes

  摘要：

  Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalized from specific carriers or intracellular sites (inflammation, neurodegenerative diseases, postischaemic reperfusion, xenobiotic intoxications, etc.), In the present work we appropriately modified an iron chelator of the hydroxychromene family in, order to obtain a tridentate chelator that would inactivate the iron redox cycle after its complexation, with a view to using this molecule in human therapy and/or in disease prevention. We synthesized such a chelator for the first time and show, by different physticochemical analysis, its tridentate nature and, importantly, its capacity to chelate iron with enough strength to inhibit both iron-dependent H2O2 generation and lipid peroxidation in in vitro biological systems.

  DOI：

  10.1021/jm021022u

文献信息

• Design, Synthesis, and Physicochemical and Biological Characterization of a New Iron Chelator of the Family of Hydroxychromenes
  作者：Marco Ferrali、Sabrina Bambagioni、Antonio Ceccanti、Donato Donati、Gianluca Giorgi、Marco Fontani、Franco Laschi、Piero Zanello、Mario Casolaro、Antonello Pietrangelo

  DOI：10.1021/jm021022u

  日期：2002.12.1

  Increasing evidence suggests that iron plays an important role in tissue damage both during chronic iron overload diseases (i.e., hemochromatosis) and when, in the absence of actual tissue iron overload, iron is delocalized from specific carriers or intracellular sites (inflammation, neurodegenerative diseases, postischaemic reperfusion, xenobiotic intoxications, etc.), In the present work we appropriately modified an iron chelator of the hydroxychromene family in, order to obtain a tridentate chelator that would inactivate the iron redox cycle after its complexation, with a view to using this molecule in human therapy and/or in disease prevention. We synthesized such a chelator for the first time and show, by different physticochemical analysis, its tridentate nature and, importantly, its capacity to chelate iron with enough strength to inhibit both iron-dependent H2O2 generation and lipid peroxidation in in vitro biological systems.