methyl 2,3-diethanethio-5-[4'-(p-fluorophenyl)-1'H-1',2',3'-triazol-1'-yl]-2,3,5-trideoxy-β-D-ribofuranoside | 1234261-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2,3-diethanethio-5-[4'-(p-fluorophenyl)-1'H-1',2',3'-triazol-1'-yl]-2,3,5-trideoxy-β-D-ribofuranoside
• 英文别名: 1-[[(2R,3R,4S,5R)-3,4-bis(ethylsulfanyl)-5-methoxyoxolan-2-yl]methyl]-4-(4-fluorophenyl)triazole
• CAS: 1234261-82-5
• 化学式: C₁₈H₂₄FN₃O₂S₂
• 分子量: 397.538
• InChiKey: HPACBFOHIWIKJM-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-diethanethio-5-[4'-(p-fluorophenyl)-1'H-1',2',3'-triazol-1'-yl]-2,3,5-trideoxy-β-D-ribofuranoside 、 O,O-二(三甲基甲硅烷基)胸苷 在 三氟甲磺酸三甲基硅酯 、 水 、 碳酸氢钠 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 12.5h， 以83%的产率得到1-[2',3'-diethanethio-5'-[4''-(p-fluorophenyl)-1''H-1'',2'',3''-triazol-1''-yl]-2',3',5'-trideoxy-β-D-ribofuranosyl]thymine
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 2′,3′-diethanethio-2′,3′,5′-trideoxy-5′-triazolonucleoside analogues

  摘要：

  A series of novel 2',3'-diethanethio-2',3',5'-trideoxy-5'-triazoloribonucleosides was synthesized in excellent yields and their antitumor activity was evaluated. These nucleoside analogues with aromatic substituted triazole rings showed significantly improved activity towards a broad range of tumor cell lines and those without arene substitutes were inactive. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.038
• 作为产物：
  描述：

  4-氟苯乙炔 、 methyl 5-azido-2,3,5-trideoxy-2,3-diethanethio-β-D-ribofuranoside 在 铜 、 copper(II) sulfate 作用下， 以 水 、 叔丁醇 为溶剂， 以86%的产率得到methyl 2,3-diethanethio-5-[4'-(p-fluorophenyl)-1'H-1',2',3'-triazol-1'-yl]-2,3,5-trideoxy-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and antitumor activity of novel 2′,3′-diethanethio-2′,3′,5′-trideoxy-5′-triazolonucleoside analogues

  摘要：

  A series of novel 2',3'-diethanethio-2',3',5'-trideoxy-5'-triazoloribonucleosides was synthesized in excellent yields and their antitumor activity was evaluated. These nucleoside analogues with aromatic substituted triazole rings showed significantly improved activity towards a broad range of tumor cell lines and those without arene substitutes were inactive. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.038