5-(N-methylimidazol-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil | 134333-64-5

• 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: 5-(N-methylimidazol-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil
• 英文别名: 1-(4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(1-methyl-1H-imidazol-2-yl)-1H-pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(1-methylimidazol-2-yl)pyrimidine-2,4-dione
• CAS: 134333-64-5
• 化学式: C₁₃H₁₆N₄O₅
• 分子量: 308.294
• InChiKey: LBTKTZHREVLEHD-IVZWLZJFSA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  碘苷 在 吡啶 、 四(三苯基膦)钯 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 5-(N-methylimidazol-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil
  参考文献：
  名称：

  5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication

  摘要：

  2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.

  DOI：

  10.1021/jm00112a011

文献信息

• 5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication
  作者：P. Wigerinck、C. Pannecouque、R. Snoeck、P. Claes、E. De Clercq、P. Herdewijn

  DOI：10.1021/jm00112a011

  日期：1991.8

  2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.