1-<2'-(t-butyl-dimethylsilyloxy)ethoxy>methyl-6-azidouracil | 219664-99-0

• 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: 1-<2'-(t-butyl-dimethylsilyloxy)ethoxy>methyl-6-azidouracil
• 英文别名: 6-Azido-1-[2-[tert-butyl(dimethyl)silyl]oxyethoxymethyl]pyrimidine-2,4-dione
• CAS: 219664-99-0
• 化学式: C₁₃H₂₃N₅O₄Si
• 分子量: 341.442
• InChiKey: HJXRGFZJOCCYBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-<2'-(t-butyl-dimethylsilyloxy)ethoxy>methyl-6-azidouracil 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以97.7%的产率得到1-<2'-(t-butyl-dimethylsilyloxy)ethoxy>methyl-6-aminouracil
  参考文献：
  名称：

  Synthesis of 5-Halogeno-6-amino-2′-deoxyurldines and their Analogs as Potential Inhibitors of Thymidine Phosphorylase

  摘要：

  5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'-deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6-amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 mu M and 6.5 mu M, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.

  DOI：

  10.1080/07328319808004324
• 作为产物：
  描述：

  1-<2'-(t-butyl-dimethylsilyloxy)ethoxy>methyl-6-iodouracil 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以79.1%的产率得到1-<2'-(t-butyl-dimethylsilyloxy)ethoxy>methyl-6-azidouracil
  参考文献：
  名称：

  Synthesis of 5-Halogeno-6-amino-2′-deoxyurldines and their Analogs as Potential Inhibitors of Thymidine Phosphorylase

  摘要：

  5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'-deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6-amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 mu M and 6.5 mu M, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.

  DOI：

  10.1080/07328319808004324

文献信息

• Synthesis of 5-Halogeno-6-amino-2′-deoxyurldines and their Analogs as Potential Inhibitors of Thymidine Phosphorylase
  作者：Bai-Chuan Pan、Zhi-Hao Chen、Edward Chu、Ming-Yu WangChu、Shih-Hsi Chu

  DOI：10.1080/07328319808004324

  日期：1998.12

  5-Halogeno-6-amino-2'-deoxyuridines were synthesized from 2'-deoxyuridine as potential thymidine phosphorylase (ThdPase) inhibitors. Among the compounds synthesized, 5-bromo-6-amino-2'-deoxyuridine (6) and 5-iodo-6-amino-2'-deoxyuridine (9) were found to inhibit ThdPase activity with IC50 values of 1.3 mu M and 6.5 mu M, respectively. In vitro cell culture studies showed that compound (6) can significantly enhance the cytotoxic effects of 5-fluoro-2'-deoxyuridine against a human colon cancer HCT-8 cell line.