tert-butyl (S)-4-((2-iodo-1-(phenylsulfonyl)-1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate | 1208307-50-9

• 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: tert-butyl (S)-4-((2-iodo-1-(phenylsulfonyl)-1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS: 1208307-50-9
• 化学式: C₂₅H₂₉IN₂O₅S
• 分子量: 596.486
• InChiKey: WOEZVBJPFPTORI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.84
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  zinc(II) cyanide 、 tert-butyl (S)-4-((2-iodo-1-(phenylsulfonyl)-1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 在 二(三叔丁基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以85%的产率得到tert-butyl (S)-4-((2-cyano-1-(phenylsulfonyl)-1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Tetrasubstituted pyridines as potent and selective AKT inhibitors: Reduced CYP450 and hERG inhibition of aminopyridines

  摘要：

  The synthesis and evaluation of tetrasubstituted aminopyridines, bearing novel azaindazole hinge binders, as potent AKT inhibitors are described. Compound 14c was identified as a potent AKT inhibitor that demonstrated reduced CYP450 inhibition and an improved developability profile compared to those of previously described trisubstituted pyridines. It also displayed dose-dependent inhibition of both phosphorylation of GSK3b and tumor growth in a BT474 tumor xenograft model in mice. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.061
• 作为产物：
  描述：

  tert-butyl (S)-2,2-dimethyl-4-((1-(phenylsulfonyl)-1H-indol-3-yl)methyl)oxazolidine-3-carboxylate 在 lithium diisopropyl amide 、 碘 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到tert-butyl (S)-4-((2-iodo-1-(phenylsulfonyl)-1H-indol-3-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Tetrasubstituted pyridines as potent and selective AKT inhibitors: Reduced CYP450 and hERG inhibition of aminopyridines

  摘要：

  The synthesis and evaluation of tetrasubstituted aminopyridines, bearing novel azaindazole hinge binders, as potent AKT inhibitors are described. Compound 14c was identified as a potent AKT inhibitor that demonstrated reduced CYP450 inhibition and an improved developability profile compared to those of previously described trisubstituted pyridines. It also displayed dose-dependent inhibition of both phosphorylation of GSK3b and tumor growth in a BT474 tumor xenograft model in mice. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.061