(2S,3R,4S)-4-amino-2-(((1-tetradecyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)tetrahydrofuran-3-ol | 1456899-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2S,3R,4S)-4-amino-2-(((1-tetradecyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)tetrahydrofuran-3-ol
• 英文别名: (2S,3R,4S)-4-amino-2-[(1-tetradecyltriazol-4-yl)methoxymethyl]oxolan-3-ol
• CAS: 1456899-50-5
• 化学式: C₂₂H₄₂N₄O₃
• 分子量: 410.6
• InChiKey: UJXKGGHFXXDOLS-FDFHNCONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-(((1-tetradecyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)tetrahydrofuran-3-yl)carbamate 在 盐酸 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、6.08 MPa 条件下， 反应 3.0h， 以87%的产率得到(2S,3R,4S)-4-amino-2-(((1-tetradecyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents

  摘要：

  Two series of more available novel 1,2,3-triazole-Jaspine B hybrids were efficiently synthesized employing click chemistry approach and evaluated for their cytotoxic activities against three human cancer cell lines (EC-9706, MGC-803 and MCF-7). Among them, compound 14h showed excellent inhibition against MCF-7 (IC50 = 1.93 μM) and was more potent than 5-Fu and Jaspine B against all three cancer cell lines. Further investigation of apoptosis assay and cell cycle analysis demonstrated that compound 14h caused cellular early and late apoptosis and arrested the cell cycle at G2/M phase in a concentration- and time-independent manner. This was the first report about the synthesis and in vitro cytotoxic evaluation of 1,2,3-triazole-Jaspine B hybrids.

  DOI：

  10.1016/j.ejmech.2014.03.022

文献信息

• Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents
  作者：Jin-Mei Xu、En Zhang、Xiao-Jing Shi、Yan-Chao Wang、Bin Yu、Wei-Wei Jiao、Ya-Zhuo Guo、Hong-Min Liu

  DOI：10.1016/j.ejmech.2014.03.022

  日期：2014.6

  Two series of more available novel 1,2,3-triazole-Jaspine B hybrids were efficiently synthesized employing click chemistry approach and evaluated for their cytotoxic activities against three human cancer cell lines (EC-9706, MGC-803 and MCF-7). Among them, compound 14h showed excellent inhibition against MCF-7 (IC50 = 1.93 μM) and was more potent than 5-Fu and Jaspine B against all three cancer cell lines. Further investigation of apoptosis assay and cell cycle analysis demonstrated that compound 14h caused cellular early and late apoptosis and arrested the cell cycle at G2/M phase in a concentration- and time-independent manner. This was the first report about the synthesis and in vitro cytotoxic evaluation of 1,2,3-triazole-Jaspine B hybrids.