3-Chloro-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride | 1179256-73-5

• 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: 3-Chloro-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride
• 英文别名: 3-chloro-4-[(2,2,2-trifluoroacetyl)amino]benzenesulfonyl chloride
• CAS: 1179256-73-5
• 化学式: C₈H₄Cl₂F₃NO₃S
• 分子量: 322.092
• InChiKey: NZZVIISZKMELCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Chloro-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride 在 sodium hydroxide 、 氨 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Novel diarylsulfonylurea derivatives as potent antimitotic agents

  摘要：

  A novel series of diarylsulfonylurea derivatives were synthesized and evaluated for interaction with tubulin and for cytotoxicity against human cancer cell lines. These derivatives demonstrated good inhibitory activity against tubulin polymerization, which was well correlated with promising antiproliferative activity as well as G2/M phase cell cycle arrest. Furthermore, several compounds were also efficacious against multidrug-resistant cancer cells, which are resistant to many other known microtubule inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.069
• 作为产物：
  描述：

  邻氯苯胺 在 吡啶 、 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-Chloro-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride
  参考文献：
  名称：

  Novel diarylsulfonylurea derivatives as potent antimitotic agents

  摘要：

  A novel series of diarylsulfonylurea derivatives were synthesized and evaluated for interaction with tubulin and for cytotoxicity against human cancer cell lines. These derivatives demonstrated good inhibitory activity against tubulin polymerization, which was well correlated with promising antiproliferative activity as well as G2/M phase cell cycle arrest. Furthermore, several compounds were also efficacious against multidrug-resistant cancer cells, which are resistant to many other known microtubule inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.069

文献信息

• Structure–activity relationship study of arylsulfonylimidazolidinones as anticancer agents
  作者：Vinay K. Sharma、Ki-Cheul Lee、Eeda Venkateswararao、Cheonik Joo、Min-Seok Kim、Niti Sharma、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2011.09.025

  日期：2011.11

  In an effort to find novel N-arylsulfonylimidazolidinones as highly potent anticancer agent, the structure–activity relationship of ethyl 2-methyl-4-(2-oxo-4-phenylimidazolidin-1-ylsulfonyl)phenylcarbamate was explored through synthesis and evaluation of in vitro cytotoxicity of its analogs against HCT116, A549 and NCL-H460 cancer cell lines. Among the synthesized derivatives, the carbamate analogs

  为了找到新型的N-芳基磺酰亚胺基咪唑啉酮类强效抗癌药，通过对2-甲基-4-（2-氧代-4-苯基咪唑烷基-1-基磺酰基）苯基氨基甲酸酯的结构和活性关系进行了探索。其类似物对HCT116，A549和NCL-H460癌细胞系的体外细胞毒性。在合成的衍生物中，氨基甲酸酯类似物（4a - f和4k - p）对所有癌细胞系均表现出对阿霉素的优异细胞毒性。这些衍生物的SAR研究证实，完整的4-苯基-1-苯磺酰氨基咪唑啉酮作为基本药效团具有关键作用，仅在1-氨基苯磺酰基部分的2位疏水取代有利于增强活性。