7-Ethoxycarbonylmethoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | 38588-55-5

• 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-Ethoxycarbonylmethoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 英文别名: [3-(4-Hydroxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic acid ethyl ester；ethyl 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetate
• CAS: 38588-55-5
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: ALMYFTPTDJRRLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  7-Ethoxycarbonylmethoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 以100%的产率得到7-carboxymethoxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  一种黄豆苷元半抗原和完全抗原及其制备方法和应用

  摘要：

  本发明公开了一种黄豆苷元半抗原和完全抗原及其制备方法和应用。所述黄豆苷元半抗原的分子结构如下式（Ⅰ）或式（Ⅱ）所示：本发明以黄豆苷元为原料，经过2步化学反应分别得到黄豆苷元7-衍生物和4`-衍生物半抗原，成功地合成了黄豆苷元半抗原，合成方法安全有效，产物纯度高。在此基础上进一步采用活泼酯法制备适合于动物免疫的黄豆苷元完全抗原，以此抗原免疫Balb/c小鼠，效价可达1：32000，抑制率可达94.9%，为建立黄豆苷元的免疫分析方法提供了核心原材料和有利条件，具有广阔的实际应用前景。

  公开号：

  CN105669628A
• 作为产物：
  描述：

  对羟基苯乙腈 在 哌啶 、 吡啶 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 生成 7-Ethoxycarbonylmethoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Structural modification and antihypertensive activity study of formononetin derivatives

  摘要：

  DOI：

  10.1080/10286020.2021.2005588

文献信息

• Ground mixture
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0129893A2

  公开（公告）日：1985-01-02

  A ground mixture of a poorly soluble cystalline drug and an adsorbent is remarkably improved in the rates of dissolution and absorption of the drug.

  将溶解性较差的胱氨酸药物和吸附剂混合研磨后，可显著提高药物的溶解和吸收率。
• 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.
• US4772627A
  申请人：——

  公开号：US4772627A

  公开（公告）日：1988-09-20
• Structural modification and antihypertensive activity study of formononetin derivatives
  作者：Sai-Jie Zuo、Dong-Lai Ma、Jing Li、Qiu-Hong Guo、Li Zhou

  DOI：10.1080/10286020.2021.2005588

  日期：2022.9.2
• 一种黄豆苷元半抗原和完全抗原及其制备方法和应用
  申请人：华南农业大学

  公开号：CN105669628A

  公开（公告）日：2016-06-15

  本发明公开了一种黄豆苷元半抗原和完全抗原及其制备方法和应用。所述黄豆苷元半抗原的分子结构如下式（Ⅰ）或式（Ⅱ）所示：本发明以黄豆苷元为原料，经过2步化学反应分别得到黄豆苷元7-衍生物和4`-衍生物半抗原，成功地合成了黄豆苷元半抗原，合成方法安全有效，产物纯度高。在此基础上进一步采用活泼酯法制备适合于动物免疫的黄豆苷元完全抗原，以此抗原免疫Balb/c小鼠，效价可达1：32000，抑制率可达94.9%，为建立黄豆苷元的免疫分析方法提供了核心原材料和有利条件，具有广阔的实际应用前景。