1-phenylcyclopropanamine 2,2,2-trifluoroacetate | 1113053-50-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-phenylcyclopropanamine 2,2,2-trifluoroacetate
• 英文别名: 1-phenylcyclopropanamine trifluoroacetic acid salt；1-Phenylcyclopropan-1-amine;2,2,2-trifluoroacetic acid
• CAS: 1113053-50-1
• 化学式: C₂HF₃O₂*C₉H₁₁N
• 分子量: 247.217
• InChiKey: TUYOEXPCAPYYOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.32
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-phenylcyclopropanamine 2,2,2-trifluoroacetate 、 3-(3-sulfamoylphenyl)-1H-indazole-5-carboxylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以26%的产率得到N-(1-phenylcyclopropyl)-3-(3-sulfamoylphenyl)-1H-indazole-5-carboxamide
  参考文献：
  名称：

  Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides

  摘要：

  TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at positions 3 and 5, respectively, establishing a novel chemical class culminating in identification of 72 (CFI-400936). This potent inhibitor of TTK (IC50=3.6nM) demonstrated good activity in cell based assay and selectivity against a panel of human kinases. A co-complex TTK X-ray crystal structure and results of a xenograft study with TTK inhibitors from this class are described.

  DOI：

  10.1016/j.bmc.2014.06.027
• 作为产物：
  描述：

  1-苯基-1-环丙羧酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 生成 1-phenylcyclopropanamine 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Discovery of inhibitors of the mitotic kinase TTK based on N-(3-(3-sulfamoylphenyl)-1H-indazol-5-yl)-acetamides and carboxamides

  摘要：

  TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at positions 3 and 5, respectively, establishing a novel chemical class culminating in identification of 72 (CFI-400936). This potent inhibitor of TTK (IC50=3.6nM) demonstrated good activity in cell based assay and selectivity against a panel of human kinases. A co-complex TTK X-ray crystal structure and results of a xenograft study with TTK inhibitors from this class are described.

  DOI：

  10.1016/j.bmc.2014.06.027

文献信息

• Solid-phase synthesis of aryl, heteroaryl, and sterically hindered alkyl amines using the Curtius rearrangement
  作者：Satoshi Sunami、Mitsuru Ohkubo

  DOI：10.1016/j.tet.2008.11.012

  日期：2009.1

  An efficient method for the solid-phase synthesis of aryl amines, heteroaryl amines, and sterically hindered alkyl amines has been developed. The key step in this process was the formation of resin-bound carbamates (B) by the Curtius rearrangement of aryl carboxylic acids with Wang resin providing the trapping hydroxyl group. N-Alkylation reactions of B gave secondary amines in good yield. Some biaryl

  已经开发了用于固相合成芳基胺，杂芳基胺和位阻烷基胺的有效方法。该过程的关键步骤是通过芳基羧酸的Curtius重排与Wang树脂提供捕获的羟基，形成与树脂结合的氨基甲酸酯（B）。B的N-烷基化反应以高收率得到仲胺。某些联芳基胺也广泛存在于生物活性物质中，还可以通过2-碘苯胺（16）或3-（4,4,5,5-四甲基-1,3， 2-二氧杂硼环烷-2-基）苯胺（21）。所开发的方法可以用于制备包含芳基，杂芳基和空间受阻的烷基胺结构作为药效基团的文库。