4-(1,2,4-triazol-1-yl)-1-(3,5-di-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one | 160452-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(1,2,4-triazol-1-yl)-1-(3,5-di-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one
• CAS: 160452-66-4
• 化学式: C₁₅H₁₇N₅O₅S
• 分子量: 379.396
• InChiKey: WXYOUVGVRQEPAM-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  118.2
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-(1,2,4-triazol-1-yl)-1-(3,5-di-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one 在 ammonium hydroxide 作用下， 生成 4-氨基-1-[(4S,5R)-4-羟基-5-(羟基甲基)四氢噻吩-2-基]嘧啶-2-酮
  参考文献：
  名称：

  Syntheses and Antitumor Activities of D-and L-2′-Deoxy-4′-thio Pyrimidine Nucleosides

  摘要：

  Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio-beta-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L-enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-alpha,beta-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.

  DOI：

  10.1080/15257779408012157
• 作为产物：
  描述：

  1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil 在 4-二甲氨基吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 0.17h， 生成 4-(1,2,4-triazol-1-yl)-1-(3,5-di-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Syntheses and Antitumor Activities of D-and L-2′-Deoxy-4′-thio Pyrimidine Nucleosides

  摘要：

  Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio-beta-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L-enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-alpha,beta-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.

  DOI：

  10.1080/15257779408012157

文献信息

• NUCLEOSIDES & NUCLEOTIDES, 1994, 13, 1347-1361
  作者：

  DOI：——

  日期：——