daidzein 7-ω-ethoxycarbonylbutyl ether | 371227-03-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: daidzein 7-ω-ethoxycarbonylbutyl ether
• 英文别名: 5-[3-(4-Hydroxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-pentanoic acid ethyl ester；ethyl 5-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxypentanoate
• CAS: 371227-03-1
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: VQAISFMOBWOMLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  daidzein 7-ω-ethoxycarbonylbutyl ether 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以20.6%的产率得到5-(3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yloxy)pentanoic acid
  参考文献：
  名称：

  Synthesis of Potential Antidipsotropic Isoflavones:  Inhibitors of the Mitochondrial Monoamine Oxidase−Aldehyde Dehydrogenase Pathway

  摘要：

  Recently we have shown that daidzin, the major active principle of an ancient herbal treatment for "alcohol addiction", suppresses ethanol intake in alcohol-preferring laboratory animals. Further, we have identified the monoamine oxidase (MAO)-aldehyde dehydrogenase (ALDH-2) pathway of the mitochondria as the potential site of action of daidzin. Daidzin analogues that potently inhibit ALDH-2 but have no or little effect on MAO are most antidipsotropic, whereas those that also inhibit MAO exhibit little, if any, antidipsotropic activity. Therefore, in the design and synthesis of more potent antidipsotropic analogues, structural features important for the inhibition of both ALDH-2 and MAO must be taken into consideration. To gain further information on the structure-activity relationships at the inhibitor binding sites of ALDH-2 and MAO, we prepared 44 analogues of daidzin and determined their potencies for ALDH-2 and MAO inhibition. Results indicate that a sufficient set of criteria for a potent antidipsotropic analogue is an isoflavone with a free 4 ' -OH function and a straight-chain alkyl substituent at the 7 position that has a terminal polar function such as -OH, -COOH, or -NH2. The preferable chain lengths for the 7-O-omega -hydroxy, 7-O-omega -carboxy, and 7-O-omega -amino subsitutents are 2 less than or equal to n less than or equal to 6, 5 less than or equal to 5 n less than or equal to 10, and n greater than or equal to 4, respectively. Analogues that meet these criteria have increased potency for ALDH-2 inhibition and/or decreased potency for MAO inhibition and therefore are likely to be potent antidipsotropic agents.

  DOI：

  10.1021/jm0101390
• 作为产物：
  描述：

  5-溴戊酸乙酯 、 大豆甙元 在 氢氧化钾 作用下， 以 水 、 丙酮 为溶剂， 反应 72.0h， 以8.8%的产率得到daidzein 7-ω-ethoxycarbonylbutyl ether
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
  [FR] COMPOSES UTILES DANS L'INHIBITION DE ALDH

  摘要：

  本发明提供了一种新型的抗酒精致病化合物。本发明进一步提供了使用所述化合物抑制ALDH-2的方法。本发明还提供了通过向个体投给本发明的化合物来调节饮酒量、酒精依赖和/或酒精滥用方法。本发明进一步提供了设计其他新型抗酒精致病化合物的理论基础。

  公开号：

  WO2004002470A1

文献信息

• Compounds useful for the inhibition of ALDH
  申请人：The Endowment for Research in Human Biology, Inc,

  公开号：US20040068003A1

  公开（公告）日：2004-04-08

  The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

  本发明提供了新型的抗酒瘾化合物。本发明还提供了使用所述化合物抑制ALDH-2的方法。本发明还提供了通过向个体施用本发明的化合物来调节饮酒、酒精依赖和/或酗酒的方法。本发明还为设计其他新型抗酒瘾化合物提供了理论依据。
• EP1542675A4
  申请人：——

  公开号：EP1542675A4

  公开（公告）日：2008-11-19
• COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
  申请人：The Endowment For Research In Human Biology, Inc.

  公开号：EP1542675A1

  公开（公告）日：2005-06-22
• US7368434B2
  申请人：——

  公开号：US7368434B2

  公开（公告）日：2008-05-06
• [EN] COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH<br/>[FR] COMPOSES UTILES DANS L'INHIBITION DE ALDH
  申请人：ENDOWMENT FOR RES IN HUMAN BIO

  公开号：WO2004002470A1

  公开（公告）日：2004-01-08

  The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

  本发明提供了一种新型的抗酒精致病化合物。本发明进一步提供了使用所述化合物抑制ALDH-2的方法。本发明还提供了通过向个体投给本发明的化合物来调节饮酒量、酒精依赖和/或酒精滥用方法。本发明进一步提供了设计其他新型抗酒精致病化合物的理论基础。