5-iodo-[5'-O-(4,4'-dimethoxytrityl)-3'-fluoro]-2',3'-dideoxyuridine | 1364916-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-iodo-[5'-O-(4,4'-dimethoxytrityl)-3'-fluoro]-2',3'-dideoxyuridine
• CAS: 1364916-81-3
• 化学式: C₃₀H₂₈FIN₂O₆
• 分子量: 658.465
• InChiKey: MQXMSSBPQWZBLN-WYMJOSIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.78
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-iodo-[5'-O-(4,4'-dimethoxytrityl)-3'-fluoro]-2',3'-dideoxyuridine 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以92%的产率得到2',3'-二脱氧-3'-氟-5-碘尿苷
  参考文献：
  名称：

  Radiolabeled Cyclosaligenyl Monophosphates of 5-Iodo-2′-deoxyuridine, 5-Iodo-3′-fluoro-2′,3′-dideoxyuridine, and 3′-Fluorothymidine for Molecular Radiotherapy of Cancer: Synthesis and Biological Evaluation

  摘要：

  Targeted molecular radiotherapy opens unprecedented opportunities to eradicate cancer cells with minimal irradiation of normal tissues. Described in this study are radioactive cyclosaligenyl monophosphates designed to deliver lethal doses of radiation to cancer cells. These compounds can be radiolabeled with SPECT- and PET-compatible radionuclides as well as radionuclides suitable for Auger electron therapies. This characteristic provides an avenue for the personalized and comprehensive treatment strategy that comprises diagnostic imaging to identify sites of disease, followed by the targeted molecular radiotherapy based on the imaging results. The developed radiosynthetic methods produce no-carrier-added products with high radiochemical yield and purity. The interaction of these compounds with their target, butyrylcholinesterase, depends on the stereochemistry around the P atom. 1050 values are in the nanomolar range. In vitro studies indicate that radiation doses delivered to the cell nucleus are sufficient to kill cells of several difficult to treat malignancies including glioblastoma and ovarian and colorectal cancers.

  DOI：

  10.1021/jm201482p
• 作为产物：
  描述：

  5-iodo-[5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-β-D-threo-pentofuranosyl]uracil 在 吡啶 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到5-iodo-[5'-O-(4,4'-dimethoxytrityl)-3'-fluoro]-2',3'-dideoxyuridine
  参考文献：
  名称：

  Radiolabeled Cyclosaligenyl Monophosphates of 5-Iodo-2′-deoxyuridine, 5-Iodo-3′-fluoro-2′,3′-dideoxyuridine, and 3′-Fluorothymidine for Molecular Radiotherapy of Cancer: Synthesis and Biological Evaluation

  摘要：

  Targeted molecular radiotherapy opens unprecedented opportunities to eradicate cancer cells with minimal irradiation of normal tissues. Described in this study are radioactive cyclosaligenyl monophosphates designed to deliver lethal doses of radiation to cancer cells. These compounds can be radiolabeled with SPECT- and PET-compatible radionuclides as well as radionuclides suitable for Auger electron therapies. This characteristic provides an avenue for the personalized and comprehensive treatment strategy that comprises diagnostic imaging to identify sites of disease, followed by the targeted molecular radiotherapy based on the imaging results. The developed radiosynthetic methods produce no-carrier-added products with high radiochemical yield and purity. The interaction of these compounds with their target, butyrylcholinesterase, depends on the stereochemistry around the P atom. 1050 values are in the nanomolar range. In vitro studies indicate that radiation doses delivered to the cell nucleus are sufficient to kill cells of several difficult to treat malignancies including glioblastoma and ovarian and colorectal cancers.

  DOI：

  10.1021/jm201482p