7-(2-nitro-4-trifluoromethylphenyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one | 1312005-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 7-(2-nitro-4-trifluoromethylphenyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one
• 英文别名: 7-[2-Nitro-4-(trifluoromethyl)phenyl]-1,3,4,5-tetrahydro-1-benzazepin-2-one
• CAS: 1312005-60-9
• 化学式: C₁₇H₁₃F₃N₂O₃
• 分子量: 350.297
• InChiKey: COBSLYOQPRUWCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(2-nitro-4-trifluoromethylphenyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 在 三苯基膦 作用下， 以 邻二氯苯 为溶剂， 反应 13.0h， 以33%的产率得到9-trifluoromethyl-3,4,5,11-tetrahydroazepino[2,3-b]carbazol-2(1H)-one
  参考文献：
  名称：

  Structure–Activity Relationships of Carboline and Carbazole Derivatives as a Novel Class of ATP-Competitive Kinesin Spindle Protein Inhibitors

  摘要：

  The kinesin spindle protein (KSP) is a mitotic kinesin involved in the establishment of a functional bipolar mitotic spindle during cell division. It is considered to be an attractive target for cancer chemotherapy with reduced side effects. Based on natural product scaffold-derived fused indole-based inhibitors and known biphenyl-type KSP inhibitors, various carboline and carbazole derivatives were synthesized and biologically evaluated. beta-Carboline and lactam-fused carbazole derivatives exhibited remarkably potent KSP inhibitory activity and mitotic arrest in prometaphase with formation of an irregular monopolar spindle. The planar tri- and tetracyclic analogs inhibited KSP ATPase in an ATP-competitive manner just like biphenyl-type inhibitors.

  DOI：

  10.1021/jm200448n
• 作为产物：
  描述：

  7-溴-4,5-二氢-1H-苯并[b]氮杂革-2(3H)-酮 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 45.0h， 生成 7-(2-nitro-4-trifluoromethylphenyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one
  参考文献：
  名称：

  Structure–Activity Relationships of Carboline and Carbazole Derivatives as a Novel Class of ATP-Competitive Kinesin Spindle Protein Inhibitors

  摘要：

  The kinesin spindle protein (KSP) is a mitotic kinesin involved in the establishment of a functional bipolar mitotic spindle during cell division. It is considered to be an attractive target for cancer chemotherapy with reduced side effects. Based on natural product scaffold-derived fused indole-based inhibitors and known biphenyl-type KSP inhibitors, various carboline and carbazole derivatives were synthesized and biologically evaluated. beta-Carboline and lactam-fused carbazole derivatives exhibited remarkably potent KSP inhibitory activity and mitotic arrest in prometaphase with formation of an irregular monopolar spindle. The planar tri- and tetracyclic analogs inhibited KSP ATPase in an ATP-competitive manner just like biphenyl-type inhibitors.

  DOI：

  10.1021/jm200448n

文献信息

• Structure–Activity Relationships of Carboline and Carbazole Derivatives as a Novel Class of ATP-Competitive Kinesin Spindle Protein Inhibitors
  作者：Tomoki Takeuchi、Shinya Oishi、Toshiaki Watanabe、Hiroaki Ohno、Jun-ichi Sawada、Kenji Matsuno、Akira Asai、Naoya Asada、Kazuo Kitaura、Nobutaka Fujii

  DOI：10.1021/jm200448n

  日期：2011.7.14

  The kinesin spindle protein (KSP) is a mitotic kinesin involved in the establishment of a functional bipolar mitotic spindle during cell division. It is considered to be an attractive target for cancer chemotherapy with reduced side effects. Based on natural product scaffold-derived fused indole-based inhibitors and known biphenyl-type KSP inhibitors, various carboline and carbazole derivatives were synthesized and biologically evaluated. beta-Carboline and lactam-fused carbazole derivatives exhibited remarkably potent KSP inhibitory activity and mitotic arrest in prometaphase with formation of an irregular monopolar spindle. The planar tri- and tetracyclic analogs inhibited KSP ATPase in an ATP-competitive manner just like biphenyl-type inhibitors.