1-(2-hydroxy-3,4-dimethoxyphenyl)-2-phenylethanone | 24852-33-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2-hydroxy-3,4-dimethoxyphenyl)-2-phenylethanone
• 英文别名: 2-hydroxy-3,4-dimethoxyphenyl benzyl ketone；2-hydroxy-3,4-dimethoxy-deoxybenzoin；2-Hydroxy-3,4-dimethoxy-desoxybenzoin
• CAS: 24852-33-3
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: JXDIUDJGJXXKLW-UHFFFAOYSA-N

物化性质

• 熔点：
  112–113°C
• 沸点：
  422.1±40.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3,4-dimethoxyphenyl)-2-phenylethanone 在 氢碘酸 、 sodium 、 乙酸酐 作用下， 生成 7,8-二羟基异黄酮
  参考文献：
  名称：

  Ballio; Pocchiari, Gazzetta Chimica Italiana, 1949, vol. 79, p. 913,918

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酸 、 2,3-二甲氧基苯酚 在 三氟化硼乙醚 作用下， 反应 1.5h， 生成 1-(2-hydroxy-3,4-dimethoxyphenyl)-2-phenylethanone
  参考文献：
  名称：

  芳烷基酮、二苯甲酮、脱氧安息香酮和查耳酮抑制 TNF-α 诱导的 ICAM-1 表达：结构-活性分析

  摘要：

  白细胞和血管内皮细胞 (EC) 之间通过细胞粘附分子的相互作用在各种炎症和自身免疫性疾病的发病机制中起着重要作用。阻断这些相互作用的小分子已成为针对急性和慢性炎症疾病的潜在治疗剂。为了鉴定有效的细胞间细胞粘附分子-1 (ICAM-1) 抑制剂，已经合成了大量的芳烷基酮、二苯甲酮、脱氧安息香和查耳酮及其类似物（共 54 种），并筛选了它们的 ICAM-1 抑制剂活动。这些化合物的构效关系研究确定了三种有效的查耳酮衍生物，并证明了其 ICAM-1 抑制活性的可能机制。

  DOI：

  10.1002/ardp.201100279

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.
• Kimoto; Honjo, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, p. 258,260
  作者：Kimoto、Honjo

  DOI：——

  日期：——
• Jain, Amolak C.; Nayyar, Naresh K.; Paliwal, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 10 - 14
  作者：Jain, Amolak C.、Nayyar, Naresh K.、Paliwal, Poonam

  DOI：——

  日期：——