5-thien-2-yl-1-(β-D-arabinofuranos-1-yl)uracil | 134333-65-6

• 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-thien-2-yl-1-(β-D-arabinofuranos-1-yl)uracil
• 英文别名: 5-(2-thienyl)uracil arabinoside；1-(3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-thiophen-2-yl-1H-pyrimidine-2,4-dione；1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-thiophen-2-ylpyrimidine-2,4-dione
• CAS: 134333-65-6
• 化学式: C₁₃H₁₄N₂O₆S
• 分子量: 326.33
• InChiKey: DCIPFACYLTURBG-ZIYJGFGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：
  148
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-thien-2-yl-2',3',5'-tri-O-acetylarabinofuranosyluracil 在 氨 作用下， 以 甲醇 为溶剂， 生成 5-thien-2-yl-1-(β-D-arabinofuranos-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