6-methylamino-3',5'-(tetraisopropyl-disiloxane-1,3-diyl)-2'-deoxyuridine | 219664-95-6

• 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: 6-methylamino-3',5'-(tetraisopropyl-disiloxane-1,3-diyl)-2'-deoxyuridine
• 英文别名: 1-[(6aR,8R,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-6-(methylamino)pyrimidine-2,4-dione
• CAS: 219664-95-6
• 化学式: C₂₂H₄₁N₃O₆Si₂
• 分子量: 499.755
• InChiKey: ZYUQTUJYBOUVJB-WAOWUJCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-methylamino-3',5'-(tetraisopropyl-disiloxane-1,3-diyl)-2'-deoxyuridine 在 溴 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以75%的产率得到5-bromo-6-methylamino-3',5'-(tetraisopropyl-disiloxane-1,3-diyl)-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
• 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 sodium azide 、 dimethyl sulfide borane 、 氢气 、 碘 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 6-methylamino-3',5'-(tetraisopropyl-disiloxane-1,3-diyl)-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.