N-(3-iodophenyl)-2,2-dichloroacetamide | 98557-59-6

• 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-(3-iodophenyl)-2,2-dichloroacetamide
• 英文别名: dichloro-acetic acid-(3-iodo-anilide)；Dichlor-essigsaeure-(3-jod-anilid)；2,2-dichloro-N-(3-iodophenyl)acetamide
• CAS: 98557-59-6
• 化学式: C₈H₆Cl₂INO
• mdl: MFCD05983431
• 分子量: 329.952
• InChiKey: TYBATNTZVQOXLU-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  409.3±45.0 °C(Predicted)
• 密度：
  1.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 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

• 作为反应物：
  描述：

  4-氯苯硼酸 、 N-(3-iodophenyl)-2,2-dichloroacetamide 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 12.0h， 以84.1%的产率得到N-(3-(4-chloro-phenyl)-phenyl)dichloroethanamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of N-arylphenyl-2,2-dichloroacetamide analogues as anti-cancer agents

  摘要：

  Our earlier research has shown that N-phenyl-2,2-dichloroacetamide analogues had much higher anticancer activity than the lead compound sodium dichloroacetate (DCA). In this current study, a variety of N-arylphenyl-2,2-dichloroacetamide analogues were synthesized via Suzuki coupling reaction and their anti-cancer activity was evaluated. The results showed that N-terphenyl-2,2-dichloroacetamide analogues had satisfactory anti-cancer activity. Among them, N-(3,5-bis(benzo[d][1,3] dioxol-5-yl)phenyl)-2,2-dichloroacetamide (6 k) had an IC50 of 2.40 mu M against KB-3-1 cells, 1.04 mu M against H460 cells and 1.73 mu M against A549 cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.057
• 作为产物：
  描述：

  二氯乙酰氯 、 3-碘苯胺 以 甲苯 为溶剂， 生成 N-(3-iodophenyl)-2,2-dichloroacetamide
  参考文献：
  名称：

  Novel N-phenyl dichloroacetamide derivatives as anticancer reagents: Design, synthesis and biological evaluation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.06.032

文献信息

• Anthelmintic compositions containing chlorine substituted amides and methods for using same
  申请人：AMERICAN CYANAMID CO

  公开号：US02877154A1

  公开（公告）日：1959-03-10