2-[(1'E,3'S)-3',4'-dihydroxybut-1'-en-1'-yl]-1,3-thiazole-4-carboxamide | 1585227-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(1'E,3'S)-3',4'-dihydroxybut-1'-en-1'-yl]-1,3-thiazole-4-carboxamide
• 英文别名: 2-[(E,3S)-3,4-dihydroxybut-1-enyl]-1,3-thiazole-4-carboxamide
• CAS: 1585227-64-0
• 化学式: C₈H₁₀N₂O₃S
• 分子量: 214.245
• InChiKey: JPXCLAVHRWPZLD-WYPBCBNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-[(1'E,3'S)-3',4'-bis(benzoyloxy)but-1'-en-1'-yl]-1,3-thiazole-4-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 144.0h， 以87%的产率得到2-[(1'E,3'S)-3',4'-dihydroxybut-1'-en-1'-yl]-1,3-thiazole-4-carboxamide
  参考文献：
  名称：

  2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity

  摘要：

  Tiazofurin analogues bearing a 5-hydroxymethy1-2-methyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (2 and 3), and two novel thiazole-based acyclo-C-nucleosides 4 and 16 have been synthesized in multistep sequences starting from D-xylose (compounds 2 and 3) or from D-arabinose (compounds 4 and 16). All synthesized analogues showed potent in vitro antitumour activities against a panel of human tumour cell lines. Flow cytometry data suggest that cytotoxic effects of analogues 2-4 and 16 in the culture of 1(562 cells might be mediated by apoptosis. It was also found that these analogues induced changes in cell cycle distribution of 1(562 cells. Results of western blot analysis (upregulation of Bax and downregulation of Bc1-2, activation of caspase-3 and the presence of a PARP cleavage product) suggest that tiazofurin mimics (2-4 and 16) in 1(562 cells induced apoptosis in a caspasedependent way. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.035