5-bromo-4-nitro-1-(2'-deoxy-β-D-ribofuranosyl)imidazole | 657408-23-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 5-bromo-4-nitro-1-(2'-deoxy-β-D-ribofuranosyl)imidazole
• 英文别名: (2R,3S,5R)-5-(5-bromo-4-nitroimidazol-1-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 657408-23-6
• 化学式: C₈H₁₀BrN₃O₅
• 分子量: 308.089
• InChiKey: ICPDLFZJALMYBV-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-bromo-4-nitro-1-(2'-deoxy-β-D-ribofuranosyl)imidazole 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-bromo-4-nitroimidazol-1-yl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  参考文献：
  名称：

  Efficient Synthesis of DNA Containing the Guanine Oxidation-Nitration Product 5-Guanidino-4-nitroimidazole:  Generation by a Postsynthetic Substitution Reaction

  摘要：

  [GRAPHICS]A convertible nucleoside was synthesized and used to prepare the 2'-deoxynucleoside of 5-guanidino-4-nitroimidazole, a putative in vivo product of the reaction of peroxynitrite with guanine. The convertible nucleoside was incorporated into an oligodeoxynucleotide by the phosphoramidite method and converted postsynthetically to yield an oligodeoxynucleotide containing 5-guanidino-4-nitroimidazole at a specific site. The oligodeoxynucleotide was inserted into a viral genome. Melting temperature analysis revealed that duplexes containing 5-guanidino-4-nitroimidazole were greatly destabilized relative to unmodified duplexes.

  DOI：

  10.1021/ol036188j
• 作为产物：
  描述：

  5-bromo-4-nitro-1-(3',5'-di-O-toluoyl-2'-deoxy-β-D-ribofuranosyl)imidazole 在 盐酸胍 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.75h， 以90%的产率得到5-bromo-4-nitro-1-(2'-deoxy-β-D-ribofuranosyl)imidazole
  参考文献：
  名称：

  Efficient Synthesis of DNA Containing the Guanine Oxidation-Nitration Product 5-Guanidino-4-nitroimidazole:  Generation by a Postsynthetic Substitution Reaction

  摘要：

  [GRAPHICS]A convertible nucleoside was synthesized and used to prepare the 2'-deoxynucleoside of 5-guanidino-4-nitroimidazole, a putative in vivo product of the reaction of peroxynitrite with guanine. The convertible nucleoside was incorporated into an oligodeoxynucleotide by the phosphoramidite method and converted postsynthetically to yield an oligodeoxynucleotide containing 5-guanidino-4-nitroimidazole at a specific site. The oligodeoxynucleotide was inserted into a viral genome. Melting temperature analysis revealed that duplexes containing 5-guanidino-4-nitroimidazole were greatly destabilized relative to unmodified duplexes.

  DOI：

  10.1021/ol036188j