4-[(2E)-3-(5-BENZOFURAN-2-YL-2,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]BENZOIC ACID

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 4-[(2E)-3-(5-BENZOFURAN-2-YL-2,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]BENZOIC ACID
• 英文别名: 4-[(E)-3-[5-(1-benzofuran-2-yl)-2,4-dimethoxyphenyl]prop-2-enoyl]benzoic acid
• 化学式: C₂₆H₂₀O₆
• 分子量: 428.441
• InChiKey: CNUJYLFWXAWEII-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-溴-2,4-二甲氧基苯甲醛 在 二(三叔丁基膦)钯 potassium fluoride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[(2E)-3-(5-BENZOFURAN-2-YL-2,4-DIMETHOXYPHENYL)-1-OXO-2-PROPENYL]BENZOIC ACID
  参考文献：
  名称：

  Carboxylated, Heteroaryl-Substituted Chalcones as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Correlations between lipophilicity determined by calculated logP values and inhibitory efficacy were observed among structurally similar compounds of the series. Various substituents were found to be tolerated at several positions of the chalcone backbone as long as the compounds fell into the right range of lipophilicity. The chalcone alpha,beta-unsaturated ketone moiety seemed to be the pharmacophore required for inhibition of VCAM-1 expression. Compound 19 showed significant antiinflammatory effects in a mouse model of allergic inflammation, indicating that this series of compounds might have therapeutic value for human asthma and other inflammatory disorders.

  DOI：

  10.1021/jm0614230

文献信息

• Process of making chalcone derivatives
  申请人：——

  公开号：US20040181075A1

  公开（公告）日：2004-09-16

  This invention is a novel methods of manufacturing chalcones that includes reacting a carbon-linked heteroaryl or heterocyclic substituted benzaldehyde with an acetophenone in a solvent or mixture of solvents in the presence of LiOMe. Also provided are new chalcones for the treatment of medical conditions.

  这项发明涉及一种新的合成查尔酮的方法，包括在溶剂或混合溶剂中，在LiOMe的存在下，将含有碳链的杂芳基或杂环取代苯甲醛与苯乙酮反应。同时提供了用于治疗医疗状况的新型查尔酮。
• [EN] PROCESS OF MAKING CHALCOME DERIVATIVES<br/>[FR] PROCEDE DE FABRICATION DE DERIVES DE CHALCONE
  申请人：ATHEROGENICS INC

  公开号：WO2004056727A2

  公开（公告）日：2004-07-08

  This invention is a novel methods of manufacturing chalcones that includes reacting a carbon-linked heteroaryl or heterocyclic substituted benzaldehyde with an acetophenone in a solvent or mixture of solvents in the presence of LiOMe. Also provided are new chalcones for the treatment of medical conditions.
• Carboxylated, Heteroaryl-Substituted Chalcones as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases
  作者：Charles Q. Meng、Liming Ni、Kimberly J. Worsencroft、Zhihong Ye、M. David Weingarten、Jacob E. Simpson、Jason W. Skudlarek、Elaine M. Marino、Ki-Ling Suen、Charles Kunsch、Amy Souder、Randy B. Howard、Cynthia L. Sundell、Martin A. Wasserman、James A. Sikorski

  DOI：10.1021/jm0614230

  日期：2007.3.1

  Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Correlations between lipophilicity determined by calculated logP values and inhibitory efficacy were observed among structurally similar compounds of the series. Various substituents were found to be tolerated at several positions of the chalcone backbone as long as the compounds fell into the right range of lipophilicity. The chalcone alpha,beta-unsaturated ketone moiety seemed to be the pharmacophore required for inhibition of VCAM-1 expression. Compound 19 showed significant antiinflammatory effects in a mouse model of allergic inflammation, indicating that this series of compounds might have therapeutic value for human asthma and other inflammatory disorders.