N-((4-(9H-purin-6-yl)phenyl)(4-chlorophenyl)methyl)-2-methylpropan-1-amine | 1562421-81-1

• 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: N-((4-(9H-purin-6-yl)phenyl)(4-chlorophenyl)methyl)-2-methylpropan-1-amine
• 英文别名: N-[(4-chlorophenyl)-[4-(7H-purin-6-yl)phenyl]methyl]-2-methylpropan-1-amine
• CAS: 1562421-81-1
• 化学式: C₂₂H₂₂ClN₅
• 分子量: 391.903
• InChiKey: ASKYTOPBQXFCBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-((4-溴苯基)-(4-氯苯基))甲醇 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 、 氯化亚砜 、 potassium acetate 、 碳酸氢钠 、 potassium carbonate 、 potassium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.33h， 生成 N-((4-(9H-purin-6-yl)phenyl)(4-chlorophenyl)methyl)-2-methylpropan-1-amine
  参考文献：
  名称：

  Structure-based design, synthesis and biological evaluation of diphenylmethylamine derivatives as novel Akt1 inhibitors

  摘要：

  A series of diphenylmethylamine derivatives were rationally designed, synthesized and biologically evaluated. Most of them exhibited moderate to good Aktl inhibitory activities, as well as promising antiproliferative efficacy against cancer cell lines. Besides, molecular docking studies were carried out to probe their binding modes with Aktl. Further kinase selectivity studies of compound 22c were performed, indicating its excellent selectivity against Aurora A, Drak, IKK beta, GSK3 beta, SYK and JAK2, and moderate selectivity against PKC and BRAF. Finally, a refined pharmacophore model was generated using the most active compounds 2, 12c and 22c via application of HipHop program. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.036

文献信息

• Structure-based design, synthesis and biological evaluation of diphenylmethylamine derivatives as novel Akt1 inhibitors
  作者：Tao Liu、Wenhu Zhan、Yanming Wang、Liangren Zhang、Bo Yang、Xiaowu Dong、Yongzhou Hu

  DOI：10.1016/j.ejmech.2013.11.036

  日期：2014.2

  A series of diphenylmethylamine derivatives were rationally designed, synthesized and biologically evaluated. Most of them exhibited moderate to good Aktl inhibitory activities, as well as promising antiproliferative efficacy against cancer cell lines. Besides, molecular docking studies were carried out to probe their binding modes with Aktl. Further kinase selectivity studies of compound 22c were performed, indicating its excellent selectivity against Aurora A, Drak, IKK beta, GSK3 beta, SYK and JAK2, and moderate selectivity against PKC and BRAF. Finally, a refined pharmacophore model was generated using the most active compounds 2, 12c and 22c via application of HipHop program. (C) 2013 Elsevier Masson SAS. All rights reserved.