N-(2,5-dichlorophenyl)-2,2-dichloroacetamide | 17090-43-6

• 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: N-(2,5-dichlorophenyl)-2,2-dichloroacetamide
• 英文别名: N-Dichloracetyl-2,5-dichloranilin；N-Dichloracetyl-2.5-dichloranilin；Dichloracet-2,5-dichloranilid；2,2-dichloro-N-(2,5-dichlorophenyl)acetamide
• CAS: 17090-43-6
• 化学式: C₈H₅Cl₄NO
• mdl: MFCD00157399
• 分子量: 272.946
• InChiKey: HJIMLUWLJJHQGK-UHFFFAOYSA-N

物化性质

• 熔点：
  150-151 °C
• 沸点：
  382.5±42.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二氯乙酸 、 2,5-二氯苯胺 在 三氯氧磷 作用下， 生成 N-(2,5-dichlorophenyl)-2,2-dichloroacetamide
  参考文献：
  名称：

  Kumar, B.H. Arun; Gowda, B. Thimme, Journal of the Indian Chemical Society, 2002, vol. 79, # 3, p. 231 - 235

  摘要：

  DOI：

文献信息

• Novel N-phenyl dichloroacetamide derivatives as anticancer reagents: Design, synthesis and biological evaluation
  作者：Yongchong Yang、Peihua Shang、Changmei Cheng、Dongchun Wang、Ping Yang、Feng Zhang、Tianwen Li、Aijun Lu、Yufen Zhao

  DOI：10.1016/j.ejmech.2010.06.032

  日期：2010.9

  A current study shows that sodium dichloroacetate (DCA) can induce cancer cell apoptosis and inhibit tumor growth, but its cytotoxic activity is low (IC50 > 1000 mu M for A549). In this paper, a variety of DCA derivatives were synthesized, and their cytotoxic activities were evaluated. The result showed that the N-phenyl-2,2-dichloroacetamide analogues had satisfactory potencies. Among them, N-(3-iodophenyl)-2,2-dichloroacetamide (3e), an optimized lead compound, has an IC50 against A549 as low as 4.76 mu M. Furthermore, it can induce cancer cell apoptosis and has a low toxicity in mice (LD50 = 1117 mg/kg). (C) 2010 Elsevier Masson SAS. All rights reserved.