1-(3'-carboxy-4'-hydroxyphenyl)-2-(3'',4''-dimethoxyphenyl)ethane | 150258-66-5

• 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-(3'-carboxy-4'-hydroxyphenyl)-2-(3'',4''-dimethoxyphenyl)ethane
• 英文别名: 5-[2-(3,4-Dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid
• CAS: 150258-66-5
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: ZGJRCBZQVVYKMS-UHFFFAOYSA-N

物化性质

• 沸点：
  462.8±45.0 °C(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3'-carboxy-4'-hydroxyphenyl)-2-(3'',4''-dimethoxyphenyl)ethane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以60%的产率得到1-(3'-carboxy-4'-hydroxyphenyl)-2-(3'',4''-dihydroxyphenyl)ethane
  参考文献：
  名称：

  Non-amine based analogs of lavendustin A as protein-tyrosine kinase inhibitors

  摘要：

  The fermentation product lavendustin A (1) is a protein-tyrosine kinase (PTK) inhibitor whose active pharmacophore has previously been shown to reside in the more simplified salicyl-containing benzylamine 2. Amine 2 bears some structural resemblance to two other natural product PTK inhibitors, erbstatin (3) and piceatannol (4). Non-amine containing analogues of 2 were therefore synthesized which incorporated additional aspects of either erbstatin or piceatannol. Examination of these inhibitors in immunoprecipitated p56lck, epidermal growth factor receptor (EGFR), and c-erb B-2/HER 2/neu PTK preparations showed that compound 12 (IC50 = 60 nM) was one of the most potent p56lck inhibitors reported to date. These results demonstrate that nitrogen is not an essential component of the lavendustin A pharmacophore 2 and that 1,2-diarylethanes and -ethenes bearing a salicyl moiety appear to be valuable structural motifs for the construction of extremely potent PTK inhibitors.

  DOI：

  10.1021/jm00072a022
• 作为产物：
  描述：

  2-(苄氧基)-5-甲酰基苯甲酸苄酯 在 palladium on activated charcoal sodium hydroxide 、 potassium tert-butylate 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 9.0h， 生成 1-(3'-carboxy-4'-hydroxyphenyl)-2-(3'',4''-dimethoxyphenyl)ethane
  参考文献：
  名称：

  Non-amine based analogs of lavendustin A as protein-tyrosine kinase inhibitors

  摘要：

  The fermentation product lavendustin A (1) is a protein-tyrosine kinase (PTK) inhibitor whose active pharmacophore has previously been shown to reside in the more simplified salicyl-containing benzylamine 2. Amine 2 bears some structural resemblance to two other natural product PTK inhibitors, erbstatin (3) and piceatannol (4). Non-amine containing analogues of 2 were therefore synthesized which incorporated additional aspects of either erbstatin or piceatannol. Examination of these inhibitors in immunoprecipitated p56lck, epidermal growth factor receptor (EGFR), and c-erb B-2/HER 2/neu PTK preparations showed that compound 12 (IC50 = 60 nM) was one of the most potent p56lck inhibitors reported to date. These results demonstrate that nitrogen is not an essential component of the lavendustin A pharmacophore 2 and that 1,2-diarylethanes and -ethenes bearing a salicyl moiety appear to be valuable structural motifs for the construction of extremely potent PTK inhibitors.

  DOI：

  10.1021/jm00072a022

文献信息

• Non-amine based analogs of lavendustin A as protein-tyrosine kinase inhibitors
  作者：Mark S. Smyth、Irena Stefanova、Frank Hartmann、Ivan D. Horak、Nir Osherov、Alexander Levitzki、Terrence R. Burke

  DOI：10.1021/jm00072a022

  日期：1993.10

  The fermentation product lavendustin A (1) is a protein-tyrosine kinase (PTK) inhibitor whose active pharmacophore has previously been shown to reside in the more simplified salicyl-containing benzylamine 2. Amine 2 bears some structural resemblance to two other natural product PTK inhibitors, erbstatin (3) and piceatannol (4). Non-amine containing analogues of 2 were therefore synthesized which incorporated additional aspects of either erbstatin or piceatannol. Examination of these inhibitors in immunoprecipitated p56lck, epidermal growth factor receptor (EGFR), and c-erb B-2/HER 2/neu PTK preparations showed that compound 12 (IC50 = 60 nM) was one of the most potent p56lck inhibitors reported to date. These results demonstrate that nitrogen is not an essential component of the lavendustin A pharmacophore 2 and that 1,2-diarylethanes and -ethenes bearing a salicyl moiety appear to be valuable structural motifs for the construction of extremely potent PTK inhibitors.