7-trifluoromethyl-9H-carbazol-2-amine | 872604-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-trifluoromethyl-9H-carbazol-2-amine
• 英文别名: 7-(trifluoromethyl)-9H-carbazol-2-ylamine；7-(trifluoromethyl)-9H-carbazol-2-amine
• CAS: 872604-14-3
• 化学式: C₁₃H₉F₃N₂
• 分子量: 250.223
• InChiKey: BQQQPQIBKHLDDY-UHFFFAOYSA-N

物化性质

• 熔点：
  274-275 °C
• 沸点：
  431.4±40.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  potassium cyanate 、 7-trifluoromethyl-9H-carbazol-2-amine 以 溶剂黄146 为溶剂， 反应 12.0h， 以27%的产率得到N-(7-trifluoromethyl-9H-carbazol-2-yl)urea
  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：

  N-Boc-4-氨基苯硼酸频哪醇酯 在 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium carbonate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 、 邻二氯苯 为溶剂， 反应 36.0h， 生成 7-trifluoromethyl-9H-carbazol-2-amine
  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

• Methods and compositions
  申请人：Dhanak Dashyant

  公开号：US20090170882A1

  公开（公告）日：2009-07-02

  Compounds, compositions and methods relating to kinesin inhibition are described herein.

  本文描述了与减少肌动蛋白抑制有关的化合物、组合物和方法。
• METHODS AND COMPOSITIONS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1771176A2

  公开（公告）日：2007-04-11
• [EN] METHODS AND COMPOSITIONS<br/>[FR] METHODES ET COMPOSITIONS
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006005063A2

  公开（公告）日：2006-01-12

  The present invention relates to pyrimidoindole and carbazole compounds represented by Formula (I) which shows inhibitory activity against KSP kinesin. The present invention also related to a method of treating cancer, hyperplasias, restenosis, cardiac hypertrophy, immune disorders, fungal disorders, and inflammation.
• 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.