4-[3E-(2, 4-DIMETHOXY-5-THIOPHEN-2-YL-PHENYL)ACRYLOYL]BENZOIC acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-[3E-(2, 4-DIMETHOXY-5-THIOPHEN-2-YL-PHENYL)ACRYLOYL]BENZOIC acid
• 英文别名: 4-[3E-(2,4-Dimethoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid；4-[(E)-3-(2,4-dimethoxy-5-thiophen-2-ylphenyl)prop-2-enoyl]benzoic acid
• 化学式: C₂₂H₁₈O₅S
• 分子量: 394.448
• InChiKey: YOSXFHPLAAXVLN-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[3E-(2, 4-DIMETHOXY-5-THIOPHEN-2-YL-PHENYL)ACRYLOYL]BENZOIC acid 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以52%的产率得到4-[2-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-cyclopropane-carbonyl]-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
• 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 、 lithium methanolate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 4-[3E-(2, 4-DIMETHOXY-5-THIOPHEN-2-YL-PHENYL)ACRYLOYL]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

• Chalcone derivatives and their use to treat diseases
  申请人：Ni Liming

  公开号：US20060189549A1

  公开（公告）日：2006-08-24

  The invention relates to compounds, pharmaceutical compositions and methods of using compounds of the general formula or its pharmaceutically acceptable salt or ester, wherein the substituents are defined in the application.

  本发明涉及一般式化合物、药物组合物及使用该一般式化合物或其药学上可接受的盐或酯的方法，其中取代基在申请中定义。
• 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。
• カルコン誘導体及び疾患を治療するためのそれらの使用
  申请人：——

  公开号：JP2005516941A

  公开（公告）日：2005-06-09

  本発明は、一般式（Ｉ）の化合物又はその医薬適合性の塩若しくはエステル（式中、置換基は本件特許出願で定義されている）の、化合物、医薬組成物及び使用に関する。 【化１】

  本发明涉及通式(I)化合物或其药用盐或酯（式中的取代基在本专利申请中定义）的化合物、药物组合物和用途。 [化学式 1.
• [EN] PROCESS OF MAKING CHALCONE DERIVATIVES<br/>[FR] PROCEDE DE FABRICATION DE DERIVES DE CHALCONE
  申请人：ATHEROGENICS INC

  公开号：WO2004056727A3

  公开（公告）日：2004-10-14
• CHALCONE DERIVATIVES AND THEIR USE TO TREAT DISEASES
  申请人：Atherogenics, Inc.

  公开号：EP1465854A2

  公开（公告）日：2004-10-13