2-(5-hydroxypentyl)chroman-4-one | 267400-90-8

• 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-hydroxypentyl)chroman-4-one
• 英文别名: 2,3-dihydro-2-(5-hydroxypentyl)-4H-1-benzopyran-4-one；2-(5-hydroxypentyl)-2,3-dihydrochromen-4-one
• CAS: 267400-90-8
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: IRXBPVKDKIYANC-UHFFFAOYSA-N

物化性质

• 沸点：
  390.6±31.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-hydroxypentyl)chroman-4-one 在 盐酸 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 3-羟基-2-(5-羟基戊基)苯并吡喃-4-酮
  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：

  2-(5-hydroxypentyl)-4H-1-benzopyran-4-one 在 H2 作用下， 以 乙醚 、 苯 为溶剂， 生成 2-(5-hydroxypentyl)chroman-4-one
  参考文献：
  名称：

  Aromatic derivatives and iron complexes thereof for the use as normalizing agents of the iron level

  摘要：

  本发明涉及式（I）的芳香族衍生物，其中：R1是（a），其中R3和R4从H和OH之间选择，前提是R3和R4不同时为H，而R2为H；或者R1和R2一起取代，为（b），其中R5从CH3和（CH2）5OH之间选择，以及它们的铁配合物，并用于制备用于调节铁水平的药物组合物。

  公开号：

  US06455578B1

文献信息

• AROMATIC DERIVATIVES AND IRON COMPLEXES THEREOF FOR THE USE AS NORMALISING AGENTS OF THE IRON LEVEL
  申请人：LABORATOIRE MEDIDOM S.A.

  公开号：EP1124814A1

  公开（公告）日：2001-08-22
• US6455578B1
  申请人：——

  公开号：US6455578B1

  公开（公告）日：2002-09-24
• [EN] AROMATIC DERIVATIVES AND IRON COMPLEXES THEREOF FOR THE USE AS NORMALISING AGENTS OF THE IRON LEVEL<br/>[FR] DERIVES AROMATIQUES ET COMPLEXES FERRIQUES DESDITS DERIVES, UTILES COMME AGENTS DE NORMALISATION DE LA SIDEREMIE
  申请人：MEDIDOM LAB

  公开号：WO2000026205A1

  公开（公告）日：2000-05-11

  The present invention is directed to aromatic derivatives of formula (I), wherein: R1 is (a), wherein R3 and R4 are selected from between H and OH, provided that R3 and R4 are not simultaneously H, and R2 is H; or R1 and R2 taken together, are (b), wherein R5 is selected from between CH3 and (CH2)5OH, to the iron complexes thereof, and to their use for the preparation of pharmaceutical compositions for the normalisation of iron level.
• 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.
• Aromatic derivatives and iron complexes thereof for the use as normalizing agents of the iron level
  申请人：Laboratoire Medidom S.A.

  公开号：US06455578B1

  公开（公告）日：2002-09-24

  The present invention is directed to aromatic derivatives of formula (I), wherein: R1 is (a), wherein R3 and R4 are selected from between H and OH, provided that R3 and R4 are not simultaneously H, and R2 is H; or R1 and R2 taken together, are (b), wherein R5 is selected from between CH3 and (CH2)5OH, to the iron complexes thereof, and to their use for the preparation of pharmaceutical compositions for the normalization of iron level.

  本发明涉及式（I）的芳香族衍生物，其中：R1是（a），其中R3和R4从H和OH之间选择，前提是R3和R4不同时为H，而R2为H；或者R1和R2一起取代，为（b），其中R5从CH3和（CH2）5OH之间选择，以及它们的铁配合物，并用于制备用于调节铁水平的药物组合物。