5-(5-chlorothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil | 134333-72-5

• 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-(5-chlorothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil
• 英文别名: 5-(5-chlorothien-2-yl)-2'-deoxyuridine；5-(5-Chloro-2-thienyl)-2'-deoxyuridine；5-(5-chlorothiophen-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 134333-72-5
• 化学式: C₁₃H₁₃ClN₂O₅S
• 分子量: 344.776
• InChiKey: RQZRQHNKLHIOQI-VAOFZXAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127
• 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 、 palladium diacetate 、 N-氯代丁二酰亚胺 、 氨 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.0h， 生成 5-(5-chlorothien-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.