7-hexyloxy-3-(4-hexyloxyphenyl)-4H-1-benzopyran-4-one

• 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: 7-hexyloxy-3-(4-hexyloxyphenyl)-4H-1-benzopyran-4-one
• 英文别名: 7-Hexoxy-3-(4-hexoxyphenyl)chromen-4-one
• 化学式: C₂₇H₃₄O₄
• 分子量: 422.565
• InChiKey: FNSWIAGNWXXPIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  溴己烷 、 大豆甙元 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以26.9%的产率得到7-hexyloxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
  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

文献信息

• Synthesis of Potential Antidipsotropic Isoflavones:  Inhibitors of the Mitochondrial Monoamine Oxidase−Aldehyde Dehydrogenase Pathway
  作者：Guang-Yao Gao、Dian-Jun Li、Wing Ming Keung

  DOI：10.1021/jm0101390

  日期：2001.9.1

  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.