1-(3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranos-1'-yl)benzimidazole-2-thione | 956475-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranos-1'-yl)benzimidazole-2-thione
• 英文别名: [(2R,3S,4R,6R)-3,4-diacetyloxy-6-(2-sulfanylidene-3H-benzimidazol-1-yl)oxan-2-yl]methyl acetate
• CAS: 956475-45-9
• 化学式: C₁₉H₂₂N₂O₇S
• 分子量: 422.459
• InChiKey: BTIUBIGZHXRDJJ-TVFCKZIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranos-1'-yl)benzimidazole-2-thione 、 3-(chloromethyl)-8-methoxycoumarin 在 ammonium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 18.5h， 以75%的产率得到2-(8'-methoxycoumarin-3'-yl)methylthio-1-(3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranos-1''-yl)benzimidazole
  参考文献：
  名称：

  Structure−Activity Relationship of New Anti-Hepatitis C Virus Agents: Heterobicycle−Coumarin Conjugates

  摘要：

  For establishment of the structure-activity relationship, 19 heterobicycle-coumarin conjugated compounds with the -SCH2- linker were synthesized and found to possess significant antiviral activities. Prominent examples included imidazopyridine-coumarin 12c, purine-coumarin 12d, and benzoxazole-coumarin 14c, which inhibited HCV replication at an EC50 of 6.8, 2.0, and 12 mu M, respectively. The heteroatoms in bicycles

  DOI：

  10.1021/jm801240d
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 、 1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以52%的产率得到1-(3',4',6'-tri-O-acetyl-2'-deoxy-β-D-glucopyranos-1'-yl)benzimidazole-2-thione
  参考文献：
  名称：

  Structure−Activity Relationship of New Anti-Hepatitis C Virus Agents: Heterobicycle−Coumarin Conjugates

  摘要：

  For establishment of the structure-activity relationship, 19 heterobicycle-coumarin conjugated compounds with the -SCH2- linker were synthesized and found to possess significant antiviral activities. Prominent examples included imidazopyridine-coumarin 12c, purine-coumarin 12d, and benzoxazole-coumarin 14c, which inhibited HCV replication at an EC50 of 6.8, 2.0, and 12 mu M, respectively. The heteroatoms in bicycles

  DOI：

  10.1021/jm801240d

文献信息

• WO2007/128086
  申请人：——

  公开号：——

  公开（公告）日：——