2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(4-chloro-phenyl)-acetamide | 867041-17-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(4-chloro-phenyl)-acetamide
• 英文别名: (Z)-2-[4-(4-Chlorobenzylidene)-2,5-dioxoimidazolidin-1-yl]-N-(4-chlorophenyl)acetamide；N-(4-chlorophenyl)-2-[4-[(4-chlorophenyl)methylidene]-2,5-dioxoimidazolidin-1-yl]acetamide
• CAS: 867041-17-6
• 化学式: C₁₈H₁₃Cl₂N₃O₃
• 分子量: 390.226
• InChiKey: HMPNYPICTVOOBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(4-chlorobenzylidene)hydantoin 、 N-(4-氯苯基)-2-氯乙酰胺 在 potassium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-[5-(4-chloro-benzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(4-chloro-phenyl)-acetamide
  参考文献：
  名称：

  Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives

  摘要：

  The synthesis and evaluation of anticancer activity of 2,4-thia(imida)zolidinedione-3- and 5-acetic acids amides were described. The structures of compounds were determined by IR, H-1 NMR, and MS analysis. In vitro anticancer activity of these compounds has been tested in National Cancer Institute (NCI) and the relationships between structure and anticancer activity are discussed. Among 2,4-azolidinedione-acetic acids derivatives 2-[5-(4-chlorobenzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide (Ic) was superior to other related compounds in terms of high selectivity for the leukemia CCRF-CEM (log GI(50) = -6.06), HL-60(TB) (log GI(50) = -6.53), MOLT-4 (log GI(50) = -6.52) and SR (log GI(50) -6.51) cell lines. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.023

文献信息

• Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives
  作者：Danylo Kaminskyy、Borys Zimenkovsky、Roman Lesyk

  DOI：10.1016/j.ejmech.2009.02.023

  日期：2009.9

  The synthesis and evaluation of anticancer activity of 2,4-thia(imida)zolidinedione-3- and 5-acetic acids amides were described. The structures of compounds were determined by IR, H-1 NMR, and MS analysis. In vitro anticancer activity of these compounds has been tested in National Cancer Institute (NCI) and the relationships between structure and anticancer activity are discussed. Among 2,4-azolidinedione-acetic acids derivatives 2-[5-(4-chlorobenzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide (Ic) was superior to other related compounds in terms of high selectivity for the leukemia CCRF-CEM (log GI(50) = -6.06), HL-60(TB) (log GI(50) = -6.53), MOLT-4 (log GI(50) = -6.52) and SR (log GI(50) -6.51) cell lines. (C) 2009 Elsevier Masson SAS. All rights reserved.