3-Chloro-4-(4-oxo-1,2,3,4-tetrahydro-carbazol-9-yl)benzonitrile | 930572-41-1

• 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: 3-Chloro-4-(4-oxo-1,2,3,4-tetrahydro-carbazol-9-yl)benzonitrile
• 英文别名: 3-chloro-4-(4-oxo-2,3-dihydro-1H-carbazol-9-yl)benzonitrile
• CAS: 930572-41-1
• 化学式: C₁₉H₁₃ClN₂O
• 分子量: 320.778
• InChiKey: XJOGHHPSNWFUGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Chloro-4-(4-oxo-1,2,3,4-tetrahydro-carbazol-9-yl)benzonitrile 在 水 、 双氧水 、 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 4-(4-oxo-2,3-dihydro-1H-carbazol-9-yl)benzamide
  参考文献：
  名称：

  Novel carbazole and acyl-indole antimitotics

  摘要：

  In the course of our Heat Shock 90 program, certain carbazole compounds were identified which had an off-target antiproliferative activity. To understand the off-target activity, we studied one analog with strong activity. We discovered that it had an effect on tubulin polymerization kinetics and was competitive with colchicine. Additional analogs were made, and a number of potent compounds were identified. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.010
• 作为产物：
  描述：

  四氢咔唑酮 、 3-氯-4-氟苯腈 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 以59%的产率得到3-Chloro-4-(4-oxo-1,2,3,4-tetrahydro-carbazol-9-yl)benzonitrile
  参考文献：
  名称：

  Carbazole derivatives

  摘要：

  本发明涉及式I的化合物和药学上可接受的盐，其中n、R1、R2、R3、X、R4、R5、R6、R8、R9和Y的定义如本文所述。式I的化合物在治疗与细胞增殖和/或异常细胞有丝分裂相关的疾病和/或病症方面有用，例如癌症、炎症和炎症相关疾病以及与血管生成相关的病症。本发明还涉及包含本发明化合物的药物组合物以及使用这些化合物治疗上述疾病和病症的方法。

  公开号：

  US20070185184A1

文献信息

• Carbazole derivatives
  申请人：Hanson J. Gunnar

  公开号：US20070185184A1

  公开（公告）日：2007-08-09

  Disclosed are compounds and pharmaceutically acceptable salts of Formula I: wherein n, R 1 , R 2 , R 3 , X, R 4 , R 5 , R 6 , R 8 , R 9 , and Y are as defined herein. Compounds of Formula I are useful in the treatment of diseases and/or conditions related to cell proliferation and/or abnormal cell mitosis, such as cancer, inflammation and inflammation-associated disorders, and conditions associated with angiogenesis. Also disclosed are pharmaceutical compositions comprising compounds of the invention and methods of treating the aforementioned conditions using such compounds.

  本发明涉及式I的化合物和药学上可接受的盐，其中n、R1、R2、R3、X、R4、R5、R6、R8、R9和Y的定义如本文所述。式I的化合物在治疗与细胞增殖和/或异常细胞有丝分裂相关的疾病和/或病症方面有用，例如癌症、炎症和炎症相关疾病以及与血管生成相关的病症。本发明还涉及包含本发明化合物的药物组合物以及使用这些化合物治疗上述疾病和病症的方法。
• Novel carbazole and acyl-indole antimitotics
  作者：Thomas E. Barta、Amy F. Barabasz、Briana E. Foley、Lifeng Geng、Steven E. Hall、Gunnar J. Hanson、Matthew Jenks、Wei Ma、John W. Rice、James Veal

  DOI：10.1016/j.bmcl.2009.04.010

  日期：2009.6

  In the course of our Heat Shock 90 program, certain carbazole compounds were identified which had an off-target antiproliferative activity. To understand the off-target activity, we studied one analog with strong activity. We discovered that it had an effect on tubulin polymerization kinetics and was competitive with colchicine. Additional analogs were made, and a number of potent compounds were identified. (C) 2009 Elsevier Ltd. All rights reserved.