β-5-(bromoethynyl)-1-<2-'deoxy-3',5'-di-O-(p-chlorobenzoyl)>-uridine | 158226-23-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: β-5-(bromoethynyl)-1-<2-'deoxy-3',5'-di-O-(p-chlorobenzoyl)>-uridine
• 英文别名: β-5-(bromoethynyl)-1-[2-'deoxy-3',5'-di-O-(p-chlorobenzoyl)]-uridine；[(2R,3S,5R)-5-[5-(2-bromoethynyl)-2,4-dioxopyrimidin-1-yl]-3-(4-chlorobenzoyl)oxyoxolan-2-yl]methyl 4-chlorobenzoate
• CAS: 158226-23-4
• 化学式: C₂₅H₁₇BrCl₂N₂O₇
• 分子量: 608.229
• InChiKey: OGIKBVKTLOXNAG-PWRODBHTSA-N

物化性质

• 密度：
  1.70±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  β-5-(bromoethynyl)-1-<2-'deoxy-3',5'-di-O-(p-chlorobenzoyl)>-uridine 在 sodium tert-pentoxide 作用下， 以 2-甲基-2-丁醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到5-溴乙炔基-2'-脱氧尿苷
  参考文献：
  名称：

  Synthesis of a potential antiviral compound: 5-bromoethynyl-2′-deoxyuridine

  摘要：

  5-Bromoethynyluracil and its deoxyriboside can be prepared in good yields starting from dibromovinyluracil, which is accesible by literature methods. 5-Bromoethynyl-deoxyuridine is less effective against HSV-I than E-(bromovinyl)deoxyuridine but, similar to BVDU, seems to exhibit a certain selectivity toward HSV-1. Molecular calculations prove the spatial similarity of both compounds.

  DOI：

  10.1016/s0040-4020(01)85560-5
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 盐酸 、 mercury dibromide 作用下， 以 吡啶 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 24.75h， 生成 β-5-(bromoethynyl)-1-<2-'deoxy-3',5'-di-O-(p-chlorobenzoyl)>-uridine
  参考文献：
  名称：

  Synthesis of a potential antiviral compound: 5-bromoethynyl-2′-deoxyuridine

  摘要：

  5-Bromoethynyluracil and its deoxyriboside can be prepared in good yields starting from dibromovinyluracil, which is accesible by literature methods. 5-Bromoethynyl-deoxyuridine is less effective against HSV-I than E-(bromovinyl)deoxyuridine but, similar to BVDU, seems to exhibit a certain selectivity toward HSV-1. Molecular calculations prove the spatial similarity of both compounds.

  DOI：

  10.1016/s0040-4020(01)85560-5

文献信息

• Synthesis of a potential antiviral compound: 5-bromoethynyl-2′-deoxyuridine
  作者：Kurt Eger、Mohammad Jalalian、Mathias Schmidt

  DOI：10.1016/s0040-4020(01)85560-5

  日期：1994.1

  5-Bromoethynyluracil and its deoxyriboside can be prepared in good yields starting from dibromovinyluracil, which is accesible by literature methods. 5-Bromoethynyl-deoxyuridine is less effective against HSV-I than E-(bromovinyl)deoxyuridine but, similar to BVDU, seems to exhibit a certain selectivity toward HSV-1. Molecular calculations prove the spatial similarity of both compounds.