7-(1-hydroxycarbonylethyl)-oxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | 99007-87-1

• 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-(1-hydroxycarbonylethyl)-oxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 英文别名: 7-(1-Carboxyethoxy)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one；2-((3-(4-Hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl)oxy)propanoic acid；2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxypropanoic acid
• CAS: 99007-87-1
• 化学式: C₁₈H₁₄O₆
• 分子量: 326.306
• InChiKey: VVOLYJNOTQWXLG-UHFFFAOYSA-N

物化性质

• 沸点：
  575.7±50.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  大豆甙元 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 7-(1-hydroxycarbonylethyl)-oxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  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

文献信息

• Treatment for osteoporosis
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04644012A1

  公开（公告）日：1987-02-17

  A compound of the formula ##STR1## wherein R.sup.1 is hydrogen or hydroxy, R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl and Y is carboxyl or a group convertible to carboxyl is effective for prevention or treatment of osteoporosis.

  式为##STR1##的化合物，其中R.sup.1是氢或羟基，R.sup.2和R.sup.3分别是氢或较低的烷基，而Y是羧基或可转化为羧基的基团，对于预防或治疗骨质疏松症是有效的。
• 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。
• Method for treating osteoporosis
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0146921A2

  公开（公告）日：1985-07-03

  A compound of the formula wherein R1 is hydrogen or hydroxy, R2 and R3 are independently hydrogen or lower alkyl and Y is carboxyl or a group convertible to carboxyl is effective for prevention or treatment of osteoporosis.

  式中的化合物 其中 R1 为氢或羟基，R2 和 R3 独立地为氢或低级烷基，Y 为羧基或可转化为羧基的基团，可有效预防或治疗骨质疏松症。
• Benzopyran-4-on derivatives and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0146922A2

  公开（公告）日：1985-07-03

  Novel benzopyran-4-on derivatives of the formula wherein R1 is hydrogen or hydroxy and R2 is lower alkyl and production theirof.

  式中 R1 为氢或羟基，R2 为低级烷基的新型苯并吡喃-4-on 衍生物及其制备方法。 其中 R1 为氢或羟基，R2 为低级烷基及其衍生物。
• ——
  作者：TSUDA MASAO、 SAWA YOICHI、 YAMAZAKI IWAO

  DOI：——

  日期：——