2,5,6-trichloro-1-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)benzimidazole | 219674-93-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 苯并咪唑核糖核苷和核糖核苷酸
• 英文名称: 2,5,6-trichloro-1-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)benzimidazole
• 英文别名: [(2S,3S,4R,5R)-3,4-diacetyloxy-5-(2,5,6-trichlorobenzimidazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 219674-93-8
• 化学式: C₁₈H₁₇Cl₃N₂O₇
• 分子量: 479.701
• InChiKey: VRCACYZEUBIEGD-MWDXBVQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5,6-trichloro-1-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)benzimidazole 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 64.0h， 生成 2-cycloheptylamino-5,6-dichloro-1-(α-L-arabinofuranosyl)benzimidazole
  参考文献：
  名称：

  Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles

  摘要：

  A number of 2-substituted-5,6-dichloro-1-(alpha-L-arabinofuranosyl)benzimidazoles have been prepared by condensation of 2-bromo-5,6-dichlorobenzimidazole or 2,5,6-trichlorobenzimidazole with tetra-O-acetyl-L-arabinofuranose. 2-Alkylamino derivatives were prepared by a substitution of the 2-chloro group with the appropriate amines. All target compounds were evaluated for activity against HCMV and HSV-1. The 2-chloro and 2-bromo derivatives showed moderate activity against HCMV at non-cytotoxic concentrations.

  DOI：

  10.1080/07328319808004326
• 作为产物：
  描述：

  2,5,6-三氯苯并咪唑 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 16.5h， 生成 2,5,6-trichloro-1-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)benzimidazole
  参考文献：
  名称：

  Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles

  摘要：

  A number of 2-substituted-5,6-dichloro-1-(alpha-L-arabinofuranosyl)benzimidazoles have been prepared by condensation of 2-bromo-5,6-dichlorobenzimidazole or 2,5,6-trichlorobenzimidazole with tetra-O-acetyl-L-arabinofuranose. 2-Alkylamino derivatives were prepared by a substitution of the 2-chloro group with the appropriate amines. All target compounds were evaluated for activity against HCMV and HSV-1. The 2-chloro and 2-bromo derivatives showed moderate activity against HCMV at non-cytotoxic concentrations.

  DOI：

  10.1080/07328319808004326

文献信息

• Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles
  作者：Jean-Luc Girardet、John C. Drach、Stanley D. Chamberlain、George W. KosLzalka、Leroy B. Townsend

  DOI：10.1080/07328319808004326

  日期：1998.12

  A number of 2-substituted-5,6-dichloro-1-(alpha-L-arabinofuranosyl)benzimidazoles have been prepared by condensation of 2-bromo-5,6-dichlorobenzimidazole or 2,5,6-trichlorobenzimidazole with tetra-O-acetyl-L-arabinofuranose. 2-Alkylamino derivatives were prepared by a substitution of the 2-chloro group with the appropriate amines. All target compounds were evaluated for activity against HCMV and HSV-1. The 2-chloro and 2-bromo derivatives showed moderate activity against HCMV at non-cytotoxic concentrations.