5-(2-aminophenylethynyl)-2,4-dimethoxybenzaldehyde | 809240-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(2-aminophenylethynyl)-2,4-dimethoxybenzaldehyde
• 英文别名: 5-[2-(2-aminophenyl)ethynyl]-2,4-dimethoxybenzaldehyde
• CAS: 809240-72-0
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: GZHVOOPGGKQIOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-aminophenylethynyl)-2,4-dimethoxybenzaldehyde 在 氯化钯 3-mercaptopropyl 、 ethyl acetate n-hexane 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以to give 0.84 g (60%) of 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde, analytical dada identical as in Ex-57D的产率得到5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde
  参考文献：
  名称：

  Sulfonamide-substituted chalcone derivatives and their use to treat diseases

  摘要：

  该发明涉及一般式的化合物、药物组成物和使用该化合物的方法，或其药学上可接受的盐或酯，其中取代基在申请中有定义。

  公开号：

  US20050049236A1
• 作为产物：
  描述：

  5-溴-2,4-二甲氧基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 、 copper(l) iodide 、 对甲苯磺酸 四丁基氟化铵 、 水 、 一氯化碘 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 苯 为溶剂， 反应 19.0h， 生成 5-(2-aminophenylethynyl)-2,4-dimethoxybenzaldehyde
  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

• Sulfonamide-substituted chalcone derivatives and their use to treat diseases
  申请人：Worsencroft J. Kimberly

  公开号：US20050049236A1

  公开（公告）日：2005-03-03

  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.

  该发明涉及一般式的化合物、药物组成物和使用该化合物的方法，或其药学上可接受的盐或酯，其中取代基在申请中有定义。
• US7173129B2
  申请人：——

  公开号：US7173129B2

  公开（公告）日：2007-02-06
• [EN] SULFONAMIDE-SUBSTITUTED CHALCONE DERIVATIVES AND THEIR USE TO TREAT DISEASES<br/>[FR] DERIVES DE CHALCONE SUBSTITUES PAR SULFONAMIDE
  申请人：ATHEROGENICS INC

  公开号：WO2004108094A2

  公开（公告）日：2004-12-16

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