7-(allyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one | 309252-39-9

• 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-(allyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-O-allyl-daidzein；7-Allyloxy-3-(4-hydroxy-phenyl)-chromen-4-one；3-(4-hydroxyphenyl)-7-prop-2-enoxychromen-4-one
• CAS: 309252-39-9
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: CQXFYCAQUMOIAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  7-(allyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 叔丁醇 为溶剂， 反应 48.0h， 以486 mg的产率得到7-O-(2,3-dihydroxypropyl)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  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
• 作为产物：
  描述：

  对羟基苯乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟化硼乙醚 作用下， 以 丙酮 为溶剂， 反应 46.5h， 生成 7-(allyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
  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

• Enhanced Osteogenic Activity of Daidzein Analogs on Human Mesenchymal Stem Cells
  申请人：THE ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND

  公开号：US20160068542A1

  公开（公告）日：2016-03-10

  Disclosed are daidzein analogs having the formula (I). Also disclosed are compositions, include a disclosed daidzein analogs, methods of preventing or treating bone disease or bone injury and/or stimulating bone growth, in a subject that include administering to the subject an effective amount of disclosed daidzein analog. Disclosed are isolated mesenchymal stem cell that has been altered by treatment a disclosed daidzein analog, daidzein, glycinol, glyceollin I, or glyceollin II, to increase the osteogenic potential of the mesenchymal stem cells.

  本发明揭示了具有公式（I）的daidzein类似物。还揭示了包括所述daidzein类似物的组合物，用于预防或治疗骨疾病或骨损伤和/或刺激骨生长的方法，包括向受体施用揭示的daidzein类似物的有效量。本发明揭示了已通过处理揭示的daidzein类似物，daidzein，glycinol，glyceollin I或glyceollin II而改变的分离的间充质干细胞，以增加间充质干细胞的成骨潜能。
• Design, Synthesis, and Osteogenic Activity of Daidzein Analogs on Human Mesenchymal Stem Cells
  作者：Amy L. Strong、Quan Jiang、Qiang Zhang、Shilong Zheng、Stephen M. Boue、Steven Elliott、Matthew E. Burow、Bruce A. Bunnell、Guangdi Wang

  DOI：10.1021/ml400397k

  日期：2014.2.13

  Osteoporosis is caused by an overstimulation of osteoclast activity and the destruction of the bone extracellular matrix. Without the normal architecture, osteoblast cells are unable to rebuild phenotypically normal bone. Hormone replacement therapy with estrogen has been effective in increasing osteoblast activity but also has resulted in the increased incidence of breast and uterine cancer. In this study we designed and synthesized a series of daidzein analogs to investigate their osteogenic induction potentials. Human bone marrow derived mesenchymal stem cells (MSCs) from three different donors were treated with daidzein analogs and demonstrated enhanced osteogenesis when compared to daidzein treatment. The enhanced osteogenic potential of these daidzein analogs resulted in increased osterix (Sp7), alkaline phosphatase (ALP), osteopontin (OPN), and insulin-like growth factor 1 (IGF-1), which are osteogenic transcription factors that regulate the maturation of osteogenic progenitor cells into mature osteoblast cells.
• MECHANICALLY INVISIBLE POLYMER COATINGS
  申请人：Danmarks Tekniske Universitet

  公开号：EP2900737B1

  公开（公告）日：2016-07-20
• ENHANCED OSTEOGENIC ACTIVITY OF DAIDZEIN ANALOGS ON HUMAN MESENCHYMAL STEM CELLS
  申请人：The Administrators of the Tulane Educational Fund

  公开号：EP2981530A2

  公开（公告）日：2016-02-10
• [EN] ENHANCED OSTEOGENIC ACTIVITY OF DAIDZEIN ANALOGS ON HUMAN MESENCHYMAL STEM CELLS<br/>[FR] ACTIVITÉ OSTÉOGÉNIQUE ACCRUE D'ANALOGUES DE LA DAIDZÉINE SUR LES CELLULES SOUCHES MÉSENCHYMATEUSES HUMAINES
  申请人：UNIV TULANE

  公开号：WO2014165723A2

  公开（公告）日：2014-10-09

  Disclosed are daidzein analogs having the formula (I). Also disclosed are compositions, include a disclosed daidzein analogs, methods of preventing or treating bone disease or bone injury and/or stimulating bone growth, in a subject that include administering to the subject an effective amount of disclosed daidzein analog. Disclosed are isolated mesenchymal stem cell that has been altered by treatment a disclosed daidzein analog, daidzein, glycinol, glyceollin I, or glyceollin II, to increase the osteogenic potential of the mesenchymal stem cells.