3-(4-aminophenyl)-7-hydroxy-4H-chromen-4-one | 77316-78-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 3-(4-aminophenyl)-7-hydroxy-4H-chromen-4-one
• 英文别名: 7-hydroxy-3-(4-aminophenyl)-4H-benzopyran-4-one；3-(4-aminophenyl)-7-hydroxychromen-4-one
• CAS: 77316-78-0
• 化学式: C₁₅H₁₁NO₃
• mdl: MFCD01544342
• 分子量: 253.257
• InChiKey: JZBZOLLJUPZBRG-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C(Solv: ethanol (64-17-5))
• 沸点：
  516.0±50.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-aminophenyl)-7-hydroxy-4H-chromen-4-one 在 硫酸 、 sodium nitrite 作用下， 生成 大豆甙元
  参考文献：
  名称：

  Bose; Dutta, Journal Of Scientific and Industrial Research, 1958, vol. 17 B, p. 266

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯乙酸 在 吡啶 、 三氟化硼乙醚 、 铁粉 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(4-aminophenyl)-7-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  异黄酮酰胺类衍生物、其制备方法和医药用途

  摘要：

  本发明涉及药物化学领域，涉及异黄酮酰胺类衍生物、其制备方法和医药用途，具体涉及一类通式为(I)的异黄酮酰胺类衍生物、它们的制备方法、含有这些化合物的药物组合物以及它们的医药用途，特别是作为预防或治疗高脂血症、肥胖症或II型糖尿病的药物的用途。

  公开号：

  CN104672192B

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。
• 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.
• Synthesis and biological evaluation of isoflavone amide derivatives with antihyperlipidemic and preadipocyte antiproliferative activities
  作者：Wenbin Wang、Yi He、Pei Xu、Qidong You、Hong Xiao、Hua Xiang

  DOI：10.1016/j.bmc.2015.06.032

  日期：2015.8

  A series of isoflavone amides were designed with isoflavone in place of the scaffold of 2-arylbenzoxazole as cholesterol ester transfer protein (CETP) inhibitors. Twelve new compounds were synthesized, and their inhibitory activities of CETP and preadipocyte proliferation were assayed. The hypolipidemic potency of the most effective compound HY-2c was further tested in vivo by hamster. The results indicate that HY-2c exhibited favorable antihyperlipidemic and preadipocyte antiproliferative activities. (C) 2015 Elsevier Ltd. All rights reserved.