5'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine | 84472-88-8

• 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'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine
• 英文别名: [(2S,3S,5R)-3-azido-5-(4-chloro-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 84472-88-8
• 化学式: C₁₁H₁₂ClN₅O₄
• 分子量: 313.7
• InChiKey: VFDXPKFSLIMVOC-QXFUBDJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 146.0h， 生成 3’-氨基-2’,3’-二脱氧胞苷
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogs of pyrimidine deoxyribonucleoside

  摘要：

  Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 microM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C X 100 value of 283.

  DOI：

  10.1021/jm00358a016
• 作为产物：
  描述：

  3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 叠氮化锂 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.33h， 生成 5'-O-acetyl-3'-azido-2',3'-dideoxy-4-chlorouridine
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogs of pyrimidine deoxyribonucleoside

  摘要：

  Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 microM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C X 100 value of 283.

  DOI：

  10.1021/jm00358a016

文献信息

• ——
  作者：LIN TAI-SHUN、 PRUSOFF W. H.

  DOI：——

  日期：——