4-chloro-benzoic acid-[erythro-4,4'-dichloro-α'-(4-chloro-benzylidenamino)-bibenzyl-α-ylamide]

• 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: 4-chloro-benzoic acid-[erythro-4,4'-dichloro-α'-(4-chloro-benzylidenamino)-bibenzyl-α-ylamide]
• 英文别名: 4-Chlor-benzoesaeure-[erythro-4,4'-dichlor-α'-(4-chlor-benzylidenamino)-bibenzyl-α-ylamid]；N-[(1R,2S)-1,2-bis(4-chlorophenyl)-2-[(4-chlorophenyl)methylideneamino]ethyl]-4-chlorobenzamide
• 化学式: C₂₈H₂₀Cl₄N₂O
• 分子量: 542.292
• InChiKey: KXXAWMDWJDXTAO-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-benzoic acid-[erythro-4,4'-dichloro-α'-(4-chloro-benzylidenamino)-bibenzyl-α-ylamide] 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 28.75h， 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
• 作为产物：
  描述：

  4-氯苯甲醛 在 ammonium acetate 作用下， 反应 3.0h， 生成 4-chloro-benzoic acid-[erythro-4,4'-dichloro-α'-(4-chloro-benzylidenamino)-bibenzyl-α-ylamide]
  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

文献信息

• Trippett, Journal of the Chemical Society, 1957, p. 4407
  作者：Trippett

  DOI：——

  日期：——
• Design, synthesis and CoMFA studies of N1-amino acid substituted 2,4,5-triphenyl imidazoline derivatives as p53–MDM2 binding inhibitors
  作者：Chunqi Hu、Xiaoxue Dou、Yizhe Wu、Lei Zhang、Yongzhou Hu

  DOI：10.1016/j.bmc.2012.01.003

  日期：2012.2

  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.