7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid | 39238-04-5

• 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-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid
• 英文别名: 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid；7-Hydroxy-4-oxo-3-phenyl-4H-chromen-2-carbonsaeure；2-carboxy-7-hydroxyisoflavone；7-Hydroxy-isoflavon-carbonsaeure-(2)；7-Hydroxy-4-oxo-3-phenylchromene-2-carboxylic acid
• CAS: 39238-04-5
• 化学式: C₁₆H₁₀O₅
• 分子量: 282.252
• InChiKey: PBOGVLQNAQZKNS-UHFFFAOYSA-N

物化性质

• 熔点：
  257-258 °C(Solv: acetone (67-64-1))
• 沸点：
  491.7±45.0 °C(Predicted)
• 密度：
  1.501±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 15.0h， 以68%的产率得到chromeno[3,4-b]chromene-6,12-dione
  参考文献：
  名称：

  一种简单的直接去氧氧化羰基脱氢类胡萝卜素的方法，其合成方法包括甾烷酮，​​鱼藤酮，6-羰基脱氢椭圆烯和6-羰基-6a，12a-脱氢deguelin

  摘要：

  据报道，有一种通过异黄酮2-羧酸直接内酯化来构建羰基-脱氢类胡萝卜素的方法。演示了该方法在天然产物首次合成中的应用，该合成物为马酮酮，6-氧代-脱氢Elliptone，鱼藤酮和6-氧代-6a，12a-脱氢deguelin。还评估了一系列氧-脱氢类胡萝卜素的生物活性。

  DOI：

  10.1002/ejoc.201900078
• 作为产物：
  描述：

  2',4'-二羟基-2-苯基苯乙酮 在 吡啶 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.0h， 生成 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid
  参考文献：
  名称：

  一种简单的直接去氧氧化羰基脱氢类胡萝卜素的方法，其合成方法包括甾烷酮，​​鱼藤酮，6-羰基脱氢椭圆烯和6-羰基-6a，12a-脱氢deguelin

  摘要：

  据报道，有一种通过异黄酮2-羧酸直接内酯化来构建羰基-脱氢类胡萝卜素的方法。演示了该方法在天然产物首次合成中的应用，该合成物为马酮酮，6-氧代-脱氢Elliptone，鱼藤酮和6-氧代-6a，12a-脱氢deguelin。还评估了一系列氧-脱氢类胡萝卜素的生物活性。

  DOI：

  10.1002/ejoc.201900078

文献信息

• [EN] COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH<br/>[FR] COMPOSES UTILES DANS L'INHIBITION DE ALDH
  申请人：ENDOWMENT FOR RES IN HUMAN BIO

  公开号：WO2004002470A1

  公开（公告）日：2004-01-08

  The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

  本发明提供了一种新型的抗酒精致病化合物。本发明进一步提供了使用所述化合物抑制ALDH-2的方法。本发明还提供了通过向个体投给本发明的化合物来调节饮酒量、酒精依赖和/或酒精滥用方法。本发明进一步提供了设计其他新型抗酒精致病化合物的理论基础。
• Compounds useful for the inhibition of ALDH
  申请人：The Endowment for Research in Human Biology, Inc,

  公开号：US20040068003A1

  公开（公告）日：2004-04-08

  The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

  本发明提供了新型的抗酒瘾化合物。本发明还提供了使用所述化合物抑制ALDH-2的方法。本发明还提供了通过向个体施用本发明的化合物来调节饮酒、酒精依赖和/或酗酒的方法。本发明还为设计其他新型抗酒瘾化合物提供了理论依据。
• Synthesis of daidzin analogues as potential agents for alcohol abuse
  作者：Guang-Yao Gao、Dian-Jun Li、Wing Ming Keung

  DOI：10.1016/s0968-0896(03)00397-3

  日期：2003.9

  Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3' and 4' positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4'-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3'-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4',7-disubstituted isoflavone. The 4'-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH2)(n)-OH with 2 less than or equal to n less than or equal to 6, -(CH2)(n)-COOH with 5 less than or equal to n less than or equal to 10, or -(CH2)(n)-NH2 with n greater than or equal to 4. (C) 2003 Elsevier Ltd. All rights reserved.
• Baker et al., Journal of the Chemical Society, 1953, p. 1852,1856
  作者：Baker et al.

  DOI：——

  日期：——
• SZABO V.; BORBELY S.; DARBAI M., MAQY. KEM. FOLYOIRAT <MGKF-A3>, 1975, 81, NO 7, 311-313
  作者：SZABO V.、 BORBELY S.、 DARBAI M.

  DOI：——

  日期：——