4-oxo-3-phenyl-4H-chromen-7-yl acetate | 13020-22-9

• 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-oxo-3-phenyl-4H-chromen-7-yl acetate
• 英文别名: 7-acetoxy-3-phenyl-chromen-4-one；7-Acetoxy-3-phenyl-chromen-4-on；7-O-acetylisoflavone；7-acetoxyisoflavone；(4-oxo-3-phenylchromen-7-yl) acetate
• CAS: 13020-22-9
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: WFVAMCNYBITPBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-3-phenyl-4H-chromen-7-yl acetate 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 135.0h， 以100%的产率得到Acetic acid 7-oxo-7a-phenyl-7,7a-dihydro-1aH-1,2-dioxa-cyclopropa[b]naphthalen-4-yl ester
  参考文献：
  名称：

  Dimethyldioxirane Epoxidation of Aurones and Isoflavones

  摘要：

  报告了在低于环境温度下，通过将黄酮（2-亚苄基苯并呋喃-3(2H)-酮，1）和异黄酮（3-芳基-4H-1-苯并吡喃-4-酮，3）与二甲基二氧杂环戊烯环氧化，合成相应的环氧物2和4。这些对酸和碱敏感的环氧物以前很难制备，但此次分离的收率很高，并通过光谱和微量分析数据得到了完全表征。现在容易获得的黄酮和/或异黄酮氧化物可以作为黄酮类天然产物的便捷前体。

  DOI：

  10.1055/s-1992-26127
• 作为产物：
  描述：

  2',4'-二羟基-2-苯基苯乙酮 在 乙醚 、 sodium acetate 作用下， 生成 4-oxo-3-phenyl-4H-chromen-7-yl acetate
  参考文献：
  名称：

  Farkas, Chemische Berichte, 1957, vol. 90, p. 2940,2943

  摘要：

  DOI：

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。
• Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
  作者：Jianzhuang Miao、Huaqing Cui、Jing Jin、Fangfang Lai、Hui Wen、Xiang Zhang、Gian Filippo Ruda、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c4cc06762b

  日期：——

  A new class of fluorophores 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) is developed and is suitable as reagents for biological imaging.

  一种新型荧光物质3-烷基-6-甲氧基-7-羟基-香豆素（AMHCs）已开发，并适用于生物成像试剂。
• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• [EN] PRODUCTION OF ISOFLAVONE DERIVATIVES<br/>[FR] DERIVES D'ISOFLAVONE
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2000049009A1

  公开（公告）日：2000-08-24

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  本文描述了一些对异黄酮进行氢化的方法，可以获得可用量的异黄酮-4-醇、异黄酮-3-烯和异黄酮。在使用药用可接受试剂和溶剂的同时，可以高纯度地获得异黄酮衍生物，并且接近定量收率。
• 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.