7-O-w-溴丙基黄豆苷元 | 309252-38-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 7-O-w-溴丙基黄豆苷元
• 英文名称: 7-O-(3-bromopropyl)-daidzein
• 英文别名: 7-O-w-Bromopropyldaidzein；7-(3-bromopropoxy)-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 309252-38-8
• 化学式: C₁₈H₁₅BrO₄
• 分子量: 375.219
• InChiKey: JMDIKMSOYUTVEL-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  咪唑 、 7-O-w-溴丙基黄豆苷元 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以48.2%的产率得到
  参考文献：
  名称：

  大豆苷元衍生物、其制备方法及应用

  摘要：

  本发明提供了一种大豆苷元衍生物，如式(I)所示，其中，R为含氮杂环基或取代的含氮杂环基；所述取代的含氮杂环基中取代基选自C1～C10的烷基；n为大于等于1的整数。与现有技术相比，本发明提供的大豆苷元衍生物对多种肿瘤细胞具有良好的生长抑制作用，尤其是当n为3时，对于A549细胞、Hela细胞与HepG2三类肿瘤细胞具有较高的抑制生长活性。

  公开号：

  CN108276394B
• 作为产物：
  描述：

  对羟基苯乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 、 三氟化硼乙醚 作用下， 以 丙酮 为溶剂， 反应 28.5h， 生成 7-O-w-溴丙基黄豆苷元
  参考文献：
  名称：

  The Mitochondrial Monoamine Oxidase−Aldehyde Dehydrogenase Pathway:  A Potential Site of Action of Daidzin

  摘要：

  Recent studies showed that daidzin suppresses ethanol intake in ethanol-preferring laboratory animals. In vitro, it potently and selectively inhibits the mitochondrial aldehyde dehydrogenase (ALDH-2). Further, it inhibits the conversion of monoamines such as serotonin (5-HT) and dopamine (DA) into their respective acid metabolites, 5-hydroxyindole-3-acetic acid (5-HIAA) and 3,4-dihydroxyphenylacetic acid (DOPAC) in isolated hamster or rat liver mitochondria. Studies on the suppression of ethanol intake and inhibition of 5-HIAA (or DOPAC) formation by six structural analogues of daidzin suggested a potential link between these two activities. This, together with the finding that daidzin does not affect the rates of mitochondria-catalyzed oxidative deamination of these monoamines, raised the possibility that the ethanol intake-suppressive (antidipsotropic) action of daidzin is not mediated by the monoamines but rather by their reactive biogenic aldehyde intermediates such as 5-hydroxyindole-3-acetaldehyde (5-HIAL) and/or 3,4-dihydroxyphenylacetaldehyde (DOPAL) which accumulate in the presence of daidzin. To further evaluate this possibility, we synthesized more structural analogues of daidzin and tested and compared their antidipsotropic activities in Syrian golden hamsters with their effects on monoamine metabolism in isolated hamster liver mitochondria using 5-HT as the substrate. Effects of daidzin and its structural analogues on the activities of monoamine oxidase (MAO) and ALDH-2, the key enzymes involved in 5-HT metabolism in the mitochondria, were also examined. Results from these studies reveal a positive correlation between the antidipsotropic activities of these analogues and their abilities to increase 5-HIAL, accumulation during 5-HT metabolism in isolated hamster liver mitochondria. Daidzin analogues that potently inhibit ALDH-2 but have no or little effect on MAO are most antidipsotropic, whereas those that also potently inhibit MAO exhibit little, if any, antidipsotropic activity. These results, although inconclusive, are consistent with the hypothesis that daidzin may act via the mitochondrial MAO/ALDH pathway and that a biogenic aldehyde such as 5-HIAL may be important in mediating its antidipsotropic action.

  DOI：

  10.1021/jm990614i

文献信息

• The Mitochondrial Monoamine Oxidase−Aldehyde Dehydrogenase Pathway:  A Potential Site of Action of Daidzin
  作者：Nadège Rooke、Dian-Jun Li、Junqing Li、Wing Ming Keung

  DOI：10.1021/jm990614i

  日期：2000.11.1

  Recent studies showed that daidzin suppresses ethanol intake in ethanol-preferring laboratory animals. In vitro, it potently and selectively inhibits the mitochondrial aldehyde dehydrogenase (ALDH-2). Further, it inhibits the conversion of monoamines such as serotonin (5-HT) and dopamine (DA) into their respective acid metabolites, 5-hydroxyindole-3-acetic acid (5-HIAA) and 3,4-dihydroxyphenylacetic acid (DOPAC) in isolated hamster or rat liver mitochondria. Studies on the suppression of ethanol intake and inhibition of 5-HIAA (or DOPAC) formation by six structural analogues of daidzin suggested a potential link between these two activities. This, together with the finding that daidzin does not affect the rates of mitochondria-catalyzed oxidative deamination of these monoamines, raised the possibility that the ethanol intake-suppressive (antidipsotropic) action of daidzin is not mediated by the monoamines but rather by their reactive biogenic aldehyde intermediates such as 5-hydroxyindole-3-acetaldehyde (5-HIAL) and/or 3,4-dihydroxyphenylacetaldehyde (DOPAL) which accumulate in the presence of daidzin. To further evaluate this possibility, we synthesized more structural analogues of daidzin and tested and compared their antidipsotropic activities in Syrian golden hamsters with their effects on monoamine metabolism in isolated hamster liver mitochondria using 5-HT as the substrate. Effects of daidzin and its structural analogues on the activities of monoamine oxidase (MAO) and ALDH-2, the key enzymes involved in 5-HT metabolism in the mitochondria, were also examined. Results from these studies reveal a positive correlation between the antidipsotropic activities of these analogues and their abilities to increase 5-HIAL, accumulation during 5-HT metabolism in isolated hamster liver mitochondria. Daidzin analogues that potently inhibit ALDH-2 but have no or little effect on MAO are most antidipsotropic, whereas those that also potently inhibit MAO exhibit little, if any, antidipsotropic activity. These results, although inconclusive, are consistent with the hypothesis that daidzin may act via the mitochondrial MAO/ALDH pathway and that a biogenic aldehyde such as 5-HIAL may be important in mediating its antidipsotropic action.
• 大豆苷元衍生物、其制备方法及应用
  申请人：北京师范大学

  公开号：CN108276394B

  公开（公告）日：2021-03-19

  本发明提供了一种大豆苷元衍生物，如式(I)所示，其中，R为含氮杂环基或取代的含氮杂环基；所述取代的含氮杂环基中取代基选自C1～C10的烷基；n为大于等于1的整数。与现有技术相比，本发明提供的大豆苷元衍生物对多种肿瘤细胞具有良好的生长抑制作用，尤其是当n为3时，对于A549细胞、Hela细胞与HepG2三类肿瘤细胞具有较高的抑制生长活性。