(5Z)-5-(3-Phenyl-2-propen-1-ylidene)-2,4-thiazolidinedione | 1144054-56-7

• 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: (5Z)-5-(3-Phenyl-2-propen-1-ylidene)-2,4-thiazolidinedione
• 英文别名: (5Z)-5-cinnamylidene-1,3-thiazolidine-2,4-dione
• CAS: 1144054-56-7
• 化学式: C₁₂H₉NO₂S
• mdl: MFCD00171164
• 分子量: 231.275
• InChiKey: XABHYXPBBJGVRA-PKFICADJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-氯苯基)-2-氯乙酰胺 、 (5Z)-5-(3-Phenyl-2-propen-1-ylidene)-2,4-thiazolidinedione 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 N-(4-chloro-phenyl)-2-[2,4-dioxo-5-(3-phenyl-allylidene)-thiazolidin-3-yl]-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
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 肉桂醛 在 sodium acetate 、 溶剂黄146 作用下， 生成 (5Z)-5-(3-Phenyl-2-propen-1-ylidene)-2,4-thiazolidinedione
  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

• A Convenient Synthesis of 5-Arylidenethiazolidine-2,4-diones Catalyzed by Alkaline Ionic Liquid
  作者：He Huang、Yi Hu、Tao Xie、Kai-Mei Fu、Hui Kang、Ping Wei

  DOI：10.3987/com-08-11533

  日期：——

  A series of 5-arylidenethiazolidine-2,4-diones was synthesized by the Knoevenagel condensation of thiazolidine-2,4-dione with aromatic aldehydes with alkaline ionic liquid 1-butyl-3-methylimidazolium hydroxide ([bmim]OH) as dual solvent and catalyst. This method provides many advantages such as being environmentally benign, simple work-up, short reaction times, obtaining in good to excellent yields, and the reusability of ionic liquid.
• Yang, De-Hong; Chen, Zhen-Chu; Chen, Song-Ying, Journal of Chemical Research - Part S, 2003, # 6, p. 330 - 331
  作者：Yang, De-Hong、Chen, Zhen-Chu、Chen, Song-Ying、Zheng, Qin-Guo

  DOI：——

  日期：——