(2S)-2-(4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carboxamido)propanoic acid | 1360627-19-5

• 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: (2S)-2-(4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carboxamido)propanoic acid
• CAS: 1360627-19-5
• 化学式: C₂₉H₂₉Cl₂N₃O₅
• 分子量: 570.472
• InChiKey: PGMZKPXKOXTKBZ-SUJMPFCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  100.46
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 (2S)-2-(4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carboxamido)propanoic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以74%的产率得到4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-N-((S)-1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl)-4,5-dihydro-1H-imidazole-1-carboxamide
  参考文献：
  名称：

  Design, synthesis and CoMFA studies of N1-amino acid substituted 2,4,5-triphenyl imidazoline derivatives as p53–MDM2 binding inhibitors

  摘要：

  A series of novel N1-amino-acid substituted 2,4,5-triphenyl imidazoline derivatives was designed and synthesized based on our previous studies. All synthesized target compounds were screened for their p53-MDM2 binding inhibitory activities and anti-proliferative activities against five cancer cell lines. Among them, twelve compounds displayed improved binding inhibitory activities and most compounds showed higher cell growth inhibition activities with IC50 values in the low micromolar range. Compound 6c exhibited marked p53-MDM2 binding inhibitory activity (IC50 = 0.59 mu M) which was eightfold more potent than that of Nutlin-1 (IC50 = 4.78 mu M). CoMFA analysis was performed based on obtained biological data and resulted in a statistically significant CoMFA model with high predict abilities (q(2) = 0.645, r(2) = 0.979). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.003
• 作为产物：
  描述：

  (4S,5R)-4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole 在 盐酸 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 (2S)-2-(4,5-bis(4-chlorophenyl)-2-(2-isopropoxy-4-methoxyphenyl)-4,5-dihydro-1H-imidazole-1-carboxamido)propanoic acid
  参考文献：
  名称：

  Design, synthesis and CoMFA studies of N1-amino acid substituted 2,4,5-triphenyl imidazoline derivatives as p53–MDM2 binding inhibitors

  摘要：

  A series of novel N1-amino-acid substituted 2,4,5-triphenyl imidazoline derivatives was designed and synthesized based on our previous studies. All synthesized target compounds were screened for their p53-MDM2 binding inhibitory activities and anti-proliferative activities against five cancer cell lines. Among them, twelve compounds displayed improved binding inhibitory activities and most compounds showed higher cell growth inhibition activities with IC50 values in the low micromolar range. Compound 6c exhibited marked p53-MDM2 binding inhibitory activity (IC50 = 0.59 mu M) which was eightfold more potent than that of Nutlin-1 (IC50 = 4.78 mu M). CoMFA analysis was performed based on obtained biological data and resulted in a statistically significant CoMFA model with high predict abilities (q(2) = 0.645, r(2) = 0.979). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.003