4’,7-dioxyethylacetate isoflavone | 40575-72-2

• 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: 4’,7-dioxyethylacetate isoflavone
• 英文别名: 7,4'-diethylcarbonylmethoxyisoflavone；ethyl 4',7-dioxyacetate isoflavones；ethyl 2-(3-{4-[(ethoxycarbonyl)methoxy]phenyl}-4-oxochromen-7-yloxy)acetate；4',7-Bis-ethoxycarbonylmethoxy-isoflavon；Ethyl 2-[4-[7-(2-ethoxy-2-oxoethoxy)-4-oxochromen-3-yl]phenoxy]acetate
• CAS: 40575-72-2
• 化学式: C₂₃H₂₂O₈
• 分子量: 426.423
• InChiKey: AUJZBVANIBYYEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4’,7-dioxyethylacetate isoflavone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以3.2%的产率得到[3-(4-Carboxymethoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic acid
  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
• 作为产物：
  描述：

  大豆甙元 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以82.8%的产率得到4’,7-dioxyethylacetate isoflavone
  参考文献：
  名称：

  异黄酮衍生物在抑制肺腺癌A549细胞增殖上 的应用

  摘要：

  本发明提供了一种具有式(Ⅰ)结构的异黄酮衍生物在抑制肺腺癌A549细胞增殖上的应用；本申请的异黄酮衍生物是一种异黄酮的酰胺类衍生物，其对人肺腺癌细胞增殖具有较好的抑制能力，可以作为具有抗肺癌细胞增殖的黄酮类新药的基础。

  公开号：

  CN105497009B

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。
• [EN] ALDH-2 INHIBITORS IN THE TREATMENT OF ADDICTION<br/>[FR] INHIBITEURS D'ALDH-2 DANS LE TRAITEMENT D'UNE ACCOUTUMANCE
  申请人：CV THERAPEUTICS INC

  公开号：WO2009094028A1

  公开（公告）日：2009-07-30

  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Formula I结构的新型异黄酮衍生物，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。
• 异黄酮衍生物在抑制人宫颈癌Hela细胞增殖上的应用
  申请人：北京师范大学

  公开号：CN105963290A

  公开（公告）日：2016-09-28

  本发明提供了一种具有式(Ⅰ)结构的异黄酮衍生物在抑制人宫颈癌Hela细胞增殖上的应用；本申请的异黄酮衍生物是一种异黄酮的羧酸盐衍生物，其对人宫颈癌Hela细胞增殖具有较好的抑制能力，可以作为具有抗宫颈癌细胞增殖的黄酮类新药的基础。
• 异黄酮衍生物及其在抗红细胞溶血上的应用
  申请人：北京师范大学

  公开号：CN105616399B

  公开（公告）日：2019-02-05

  本发明提供了一种具有式(I)结构的异黄酮衍生物在抗红细胞溶血上的应用。本申请提供的异黄酮类衍生物具有良好的水溶性，可以较好的清除自由基，具有抗红细胞溶血的作用。实验结果表明，本申请提供的异黄酮衍生物具有良好的抗红细胞溶血的作用。