5-chloro-6-amino-2'-deoxyuridine

• 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-chloro-6-amino-2'-deoxyuridine
• 英文别名: 6-amino-5-chloro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₉H₁₂ClN₃O₅
• 分子量: 277.664
• InChiKey: AYKJIXCECMTHFY-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-DISILOXANEDIYL)-2'-脱氧尿苷 在 palladium on activated charcoal N-氯代丁二酰亚胺 、 sodium azide 、 四丁基氟化铵 、 氢气 、 碘 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 5-chloro-6-amino-2'-deoxyuridine
  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.