(E)-5-[2-(Bezn基氧基)2-[2,5-二(苄氧基)苯基]乙烯基]-苯甲酸 | 150258-61-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (E)-5-[2-(Bezn基氧基)2-[2,5-二(苄氧基)苯基]乙烯基]-苯甲酸
• 英文名称: trans-1-(3'-carboxy-4'-(benzyloxy)phenyl)-2-(2'',5''-bis(benzyloxy)phenyl)ethene
• 英文别名: (E)-5-[2-(Beznyloxy)2-[2,5-bis(benzyloxy)phenyl]ethenyl]-benzoic Acid；5-[(E)-2-[2,5-bis(phenylmethoxy)phenyl]ethenyl]-2-phenylmethoxybenzoic acid
• CAS: 150258-61-0
• 化学式: C₃₆H₃₀O₅
• 分子量: 542.631
• InChiKey: ZWCDVZXJPYEJDC-FBMGVBCBSA-N

物化性质

• 溶解度：
  可溶于氯仿、甲醇、四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-(苄氧基)-5-甲酰基苯甲酸苄酯	benzyl 5-formyl-2-(benzyloxy)benzoate	150258-60-9	C22H18O4	346.383

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5-[(1E)-2-(2,5-二羟基苯基)乙烯基]-2-羟基-苯甲酸	trans-1-(3'-carboxy-4'-hydroxyphenyl)-2-(2'',5''-dihydroxyphenyl)ethene	150258-63-2	C15H12O5	272.257

反应信息

• 作为反应物：
  描述：

  (E)-5-[2-(Bezn基氧基)2-[2,5-二(苄氧基)苯基]乙烯基]-苯甲酸 生成 5-[(1E)-2-(2,5-二羟基苯基)乙烯基]-2-羟基-苯甲酸
  参考文献：
  名称：

  Disubstituted lavendustin A analogs and pharmaceutical compositions comprising the analogs

  摘要：

  描述了具有抗增殖活性的PTK抑制剂的二取代拉文杜斯汀A类似物。本发明的优选化合物，不受限于，满足Formula 1或Formula 2中的任一种。根据体内生物活性，目前优选的化合物是4'-金刚烷基苯甲酸酯-1'-N-1,4-二羟基苯乙胺和4'-金刚烷基甲基苯甲酸酯-1'-N-1,4-二羟基苯乙胺。本发明还提供了含有二取代拉文杜斯汀A类似物有效量的药物组合物。这种组合物还可以包括其他活性成分、传统用于制备药物组合物的其他材料以及它们的混合物。本发明的化合物和组合物可用于治疗受试者，例如，在治疗增殖性疾病中抑制活细胞的增殖。

  公开号：

  EP1367046A9
• 作为产物：
  描述：

  2-(苄氧基)-5-甲酰基苯甲酸苄酯 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (E)-5-[2-(Bezn基氧基)2-[2,5-二(苄氧基)苯基]乙烯基]-苯甲酸
  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

• Disubstituted lavendustin A analogs and pharmaceutical compositions comprising the analogs
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1367046A9

  公开（公告）日：2004-05-12

  Disubstituted lavendustin A analogs that are PTK inhibitors having antiproliferative activity are described. Preferred compounds of the present invention, without limitation, satisfy either Formula 1 or Formula 2. Currently preferred compounds ,based on in vivo biological activity, are 4'-adamantylbenzoate-1'-N-1,4-dihydroxybenzylamine and 4'-adamantylmethylbenzoate-1'-N-1,4-dihydroxybenzylamine. The present invention also provides pharmaceutical compositions comprising effective amounts of disubstituted lavendustin A analogs. Such compositions also may comprise other active ingredients, other materials conventionally used in the formulation of pharmaceutical composition, and mixtures thereof. The compounds and compositions of the present invention can be used for treating subjects to, for example, inhibit the proliferation of living cells in the treatment of proliferative diseases.

  描述了具有抗增殖活性的PTK抑制剂的二取代拉文杜斯汀A类似物。本发明的优选化合物，不受限于，满足Formula 1或Formula 2中的任一种。根据体内生物活性，目前优选的化合物是4'-金刚烷基苯甲酸酯-1'-N-1,4-二羟基苯乙胺和4'-金刚烷基甲基苯甲酸酯-1'-N-1,4-二羟基苯乙胺。本发明还提供了含有二取代拉文杜斯汀A类似物有效量的药物组合物。这种组合物还可以包括其他活性成分、传统用于制备药物组合物的其他材料以及它们的混合物。本发明的化合物和组合物可用于治疗受试者，例如，在治疗增殖性疾病中抑制活细胞的增殖。
• 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.