dibenzyl (4-(4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)phosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: dibenzyl (4-(4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)phosphonate
• 英文别名: 2-N-[4-[1-bis(phenylmethoxy)phosphorylpiperidin-4-yl]-5-methyl-2-propan-2-yloxyphenyl]-5-chloro-4-N-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine
• 化学式: C₄₂H₄₉ClN₅O₆PS
• 分子量: 818.374
• InChiKey: CSELLWYGLKWBBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dibenzyl (4-(4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)phosphonate 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到benzyl hydrogen (4-(4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)phosphonate
  参考文献：
  名称：

  Synthesis and anticancer activities of ceritinib analogs modified in the terminal piperidine ring

  摘要：

  A series of new ceritinib analogs by extensive functionalization of the tail piperidine ring with various phosphamides and carbamates have been synthesized. All the ceritinib derivatives were evaluated for their cytotoxic activities against H2228 cell line. From the activity profile obtained, three of the tested compounds (compounds 4, 7 and 9) showed significant cytotoxic effects. Among these derivatives compound 9 was found to possess cytotoxicity that is better than standard drug ceritinib (IC50 = 24 nM). Moreover, compound 9 demonstrated robust tumor growth inhibition in vivo model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.056
• 作为产物：
  描述：

  4-(4-氨基-5-异丙氧基-2-甲基苯基)哌啶-1-羧酸叔丁酯 在 palladium diacetate 、 caesium carbonate 、 三乙胺 、 三氟乙酸 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 dibenzyl (4-(4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)phosphonate
  参考文献：
  名称：

  Synthesis and anticancer activities of ceritinib analogs modified in the terminal piperidine ring

  摘要：

  A series of new ceritinib analogs by extensive functionalization of the tail piperidine ring with various phosphamides and carbamates have been synthesized. All the ceritinib derivatives were evaluated for their cytotoxic activities against H2228 cell line. From the activity profile obtained, three of the tested compounds (compounds 4, 7 and 9) showed significant cytotoxic effects. Among these derivatives compound 9 was found to possess cytotoxicity that is better than standard drug ceritinib (IC50 = 24 nM). Moreover, compound 9 demonstrated robust tumor growth inhibition in vivo model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.056

文献信息

• Synthesis and anticancer activities of ceritinib analogs modified in the terminal piperidine ring
  作者：Peng Wang、Jin Cai、Junqing Chen、Min Ji

  DOI：10.1016/j.ejmech.2015.01.056

  日期：2015.3

  A series of new ceritinib analogs by extensive functionalization of the tail piperidine ring with various phosphamides and carbamates have been synthesized. All the ceritinib derivatives were evaluated for their cytotoxic activities against H2228 cell line. From the activity profile obtained, three of the tested compounds (compounds 4, 7 and 9) showed significant cytotoxic effects. Among these derivatives compound 9 was found to possess cytotoxicity that is better than standard drug ceritinib (IC50 = 24 nM). Moreover, compound 9 demonstrated robust tumor growth inhibition in vivo model. (C) 2015 Elsevier Masson SAS. All rights reserved.