7-乙氧基-3-(4-羟基苯基)-4H-苯并吡喃-4-酮 | 146698-96-6

• 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-乙氧基-3-(4-羟基苯基)-4H-苯并吡喃-4-酮
• 中文别名: 7-O-乙基黄豆苷原
• 英文名称: 7-ethoxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 3-(4-hydroxyphenyl)-7-ethoxychromen-4-one；7-ethoxy-4'-hydroxyisoflavone；7-ethoxyl-4’-hydroxyisoflavone；7-O-ethyl-daidzein；7-Ethoxy-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 146698-96-6
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: YMGLMEIZDQKJBW-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212°C
• 溶解度：
  溶于DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-乙氧基-3-(4-羟基苯基)-4H-苯并吡喃-4-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以93%的产率得到5-ethoxy-2-[4-(4-hydroxyphenyl)-1H-pyrazol-3-yl]phenol
  参考文献：
  名称：

  天然异黄酮和水合肼精确合成一锅3,4-二芳基-1 H-吡唑

  摘要：

  通过使水合肼与不同的天然异黄酮或其衍生物反应，已经开发了一种有效的方案，用于制备一系列新的3,4-二芳基-1 H-吡唑类，具有潜在的药理学和农业目标。在耐受各种官能团的相当温和的反应条件（80°）下，以良好至优异的收率（80-95％；表2）获得了目标化合物。完全表征了这些新化合物，并确定了3,5-二乙氧基-2- [4-（4-乙氧基苯基）-1 H-吡唑-3-基]苯酚（26）的单晶X射线结构过乙酰化的化合物2- {1-乙酰基-4- [4-乙酰氧基-3-（二乙酰氨基）苯基] -1 H-吡唑-3-基} -5-乙酰氧基苯乙酸（35）已解决（图）。

  DOI：

  10.1002/hlca.200790217
• 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 二甲基亚砜 为溶剂， 反应 28.5h， 生成 7-乙氧基-3-(4-羟基苯基)-4H-苯并吡喃-4-酮
  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
• 作为试剂：
  描述：

  大豆甙元 、 碘甲烷 在 potassium carbonate 、 7-乙氧基-3-(4-羟基苯基)-4H-苯并吡喃-4-酮 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以27%的产率得到3-(4-羟基苯基)-7-甲氧基-4H-色烯-4-酮
  参考文献：
  名称：

  Daidzein analogs as treatment for cancer

  摘要：

  提供了用于治疗癌症的组合物，包括至少一种新型的大豆异黄酮类似物，以及使用它们预防或治疗癌症或肿瘤生长的方法。

  公开号：

  US09669004B2

文献信息

• ALDH-2 INHIBITORS IN THE TREATMENT OF DRUG ADDICTION
  申请人：Zablocki Jeff

  公开号：US20080032995A1

  公开（公告）日：2008-02-07

  Disclosed are novel isoflavone derivatives having the structure of Formula I which are useful as ALDH-2 inhibitors for treating mammals for dependence upon drugs of addiction, for example addiction to dopamine-producing agent such as cocaine, morphine, amphetamines, nicotine, and alcohol.

  揭示了具有以下结构的新型异黄酮衍生物，其可用作ALDH-2抑制剂，用于治疗哺乳动物对成瘾药物的依赖，例如对多巴胺类药物如可卡因、吗啡、安非他命、尼古丁和酒精的依赖。
• ALDH-2 INHIBITORS IN THE TREATMENT OF PSYCHIATRIC DISORDERS
  申请人：Diamond Ivan

  公开号：US20090124672A1

  公开（公告）日：2009-05-14

  Disclosed are isoflavone derivatives having the structure of Formula I which are useful as ALDH-2 inhibitors for use treating in mammals suffering from psychiatric disorders such as, for example, depression, generalized anxiety, social phobia, panic disorder, and sleep disorders.

  披露的是具有公式I结构的异黄酮衍生物，它们作为ALDH-2抑制剂，用于治疗遭受精神疾病困扰的哺乳动物，例如抑郁症、广泛性焦虑症、社交恐惧症、恐慌症和睡眠障碍。
• Synthesis and crystal structure of 7-ethoxyl-4′-hydroxyisoflavone
  作者：Zun-Ting Zhang、Qiu-Ya Wang、Yun He、Kai-Bai Yu

  DOI：10.1007/s10870-005-2795-2

  日期：2005.2

  7-Ethoxyl-4′-hydroxyisoflavone was prepared and its crystal structure was examined by X-ray diffraction. Crystallization of the title compound occurs in the monoclinic, space group P2(1)/c with a = 11.144(2) Å, b = 10.209(1) Å, c = 13.191(2) Å, β = 113.43(1)∘ and Z = 4. The molecular structure of title compound consists of a benzopyranone moiety, a phenyl moiety, a hydroxyl and an ethoxyl group. The benzopyranone ring is not coplanar with the phenyl ring, the dihedral angle being 46.75∘. The ethoxyl group is nearly coplanar with its corresponding ring with the torsion angle 175.23(2)∘. Three kinds of hydrogen bond and two kinds of aromatic stacking interaction link the title compounds into a three-dimensional networking structure.

  制备了 7-乙氧基-4′-羟基异黄酮，并通过 X 射线衍射研究了其晶体结构。标题化合物结晶为单斜晶系，空间群为 P2(1)/c，a = 11.144(2)埃，b = 10.209(1)埃，c = 13.191(2)埃，β = 113.43(1)∘，Z = 4。标题化合物的分子结构由一个苯并吡喃酮分子、一个苯基分子、一个羟基和一个乙氧基组成。苯并吡喃酮环与苯基环不共面，二面角为 46.75∘。乙氧基与其对应的环几乎共面，扭转角为 175.23(2)∘。三种氢键和两种芳香堆积作用将标题化合物连接成一个三维网络结构。
• ALDH-2 INHIBITORS IN THE TREATMENT OF ADDICTION
  申请人：Zablocki Jeff

  公开号：US20080207610A1

  公开（公告）日：2008-08-28

  Disclosed are novel isoflavone derivatives having the structure of Formula I which are useful as ALDH-2 inhibitors for treating mammals for dependence upon drugs of addiction, for example addiction to dopamine-producing agent such as cocaine, morphine, amphetamines, nicotine, and alcohol.

  本发明揭示了一种新型异黄酮衍生物，其具有I式结构，可用作ALDH-2抑制剂，用于治疗哺乳动物对成瘾药物的依赖，例如对多巴胺产生剂如可卡因、吗啡、安非他命、尼古丁和酒精的成瘾。
• 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。