(Z)-3-(4-(trifluoromethyl)benzyl)-5-(4-aminobenzylidene)thiazolidine-2,4-dione | 1442655-25-5

• 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: (Z)-3-(4-(trifluoromethyl)benzyl)-5-(4-aminobenzylidene)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(4-aminophenyl)methylidene]-3-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 1442655-25-5
• 化学式: C₁₈H₁₃F₃N₂O₂S
• 分子量: 378.375
• InChiKey: LRHXRGOFMNLSJN-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-溴丙烯酸 、 (Z)-3-(4-(trifluoromethyl)benzyl)-5-(4-aminobenzylidene)thiazolidine-2,4-dione 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以52%的产率得到N-(4-((Z)-(3-(4-trifluoromethylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide
  参考文献：
  名称：

  Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione

  摘要：

  Hybridization of two different bioactive molecules with different mechanism of action is one of the methods that are being adopted to treat cancer. Molecules bearing a thiazolidine-2,4-dione scaffold have been recognized as antineoplastic agents with a broad spectrum of activity against many cancer cell lines. In this manuscript we have described the synthesis and biological evaluation of two series of N-3-substituted-5-arylidene thiazolidine-2,4-diones, bearing the alpha-bromoacryloylamido moiety at the para- or meta-position on the phenyl of the arylidene portion. We have observed that selected compounds 5a, 5c and 5g suppress proliferation of human myeloid leukaemia HL-60 and U937 cells by triggering morphological changes and internucleosomal DNA fragmentation, which are well-known features of apoptosis. Finally, our results indicated that the investigated compounds induced apoptotic cell death through a mechanism that involved activation of multiple caspases and was also associated with the release of cytochrome c from the mitochondria. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.030
• 作为产物：
  描述：

  5-(4-nitro-benzylidene)-thiazolidine-2,4-dione 在 盐酸 、 铁粉 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (Z)-3-(4-(trifluoromethyl)benzyl)-5-(4-aminobenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione

  摘要：

  Hybridization of two different bioactive molecules with different mechanism of action is one of the methods that are being adopted to treat cancer. Molecules bearing a thiazolidine-2,4-dione scaffold have been recognized as antineoplastic agents with a broad spectrum of activity against many cancer cell lines. In this manuscript we have described the synthesis and biological evaluation of two series of N-3-substituted-5-arylidene thiazolidine-2,4-diones, bearing the alpha-bromoacryloylamido moiety at the para- or meta-position on the phenyl of the arylidene portion. We have observed that selected compounds 5a, 5c and 5g suppress proliferation of human myeloid leukaemia HL-60 and U937 cells by triggering morphological changes and internucleosomal DNA fragmentation, which are well-known features of apoptosis. Finally, our results indicated that the investigated compounds induced apoptotic cell death through a mechanism that involved activation of multiple caspases and was also associated with the release of cytochrome c from the mitochondria. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.030