5-iodo-O,O'-(di-tert-butyl)-2'-deoxyuridine-5'-yl monophosphate | 848318-67-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-iodo-O,O'-(di-tert-butyl)-2'-deoxyuridine-5'-yl monophosphate
• 英文别名: ditert-butyl [(2R,3S,5R)-3-hydroxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl phosphate
• CAS: 848318-67-2
• 化学式: C₁₇H₂₈IN₂O₈P
• 分子量: 546.296
• InChiKey: WFJAPRKACRPFIG-YNEHKIRRSA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-iodo-O,O'-(di-tert-butyl)-2'-deoxyuridine-5'-yl monophosphate 、 dihydrotestosterone hemisuccinate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到5-iodo-3'-O-(17β-succinyl-5α-androstan-3-one)-O,O'-(di-tert-butyl)-2'-deoxyuridin-5'-yl monophosphate
  参考文献：
  名称：

  Cancer specific radiolabeled conjugates regulated by the cell cycle for the treatment and diagnosis of cancer

  摘要：

  揭示了具有一种有效靶向肿瘤细胞的成分的放射性标记结合物，这些细胞选择性地吸收和降解结合物，从而将能够被核物质吸收的放射性同位素传递至肿瘤细胞核，以产生细胞毒作用和/或使细胞可通过放射成像检测。

  公开号：

  US20050069495A1
• 作为产物：
  描述：

  在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 以0.94 g的产率得到5-iodo-O,O'-(di-tert-butyl)-2'-deoxyuridine-5'-yl monophosphate
  参考文献：
  名称：

  Radiolabeled 5-Iodo-3′-O-(17β-succinyl-5α-androstan-3-one)-2′-deoxyuridine and Its 5′-Monophosphate for Imaging and Therapy of Androgen Receptor-Positive Cancers: Synthesis and Biological Evaluation

  摘要：

  High levels of androgen receptor (AR) are often indicative of recurrent, advanced, or metastatic cancers. These conditions are also characterized by a high proliferative fraction. 5-Radioiodo-3'-O-(17 beta-succinyl-5 alpha-androstan-3-one)-2'-deoxyuridine 8 and 5-radioiodo-3'-O-(17 beta-succinyl-5 alpha-androstan-3-one)-2'-deoxyuridin-5'-yl monophosphate 13 target AR. They are also degraded intracellularly to 5-radioiodo-2'-deoxyuridine 1 and its monophosphate 20. respectively, which can participate in the DNA synthesis. Both drugs were prepared at the no-carrier-added level. Precursors and methods are readily adaptable to radiolabeling with various radiohalides suitable for SPECT and PET imaging, its well as endoradiotherapy, In vitro and in vivo studies confirm the AR-dependent interactions. Both drugs bind to sex hormone binding globulin. This binding significantly improves their stability in serum. Biodistribution and imaging studies show preferential uptake and retention of 8 and 13 in ip xenografts of human ovarian adenocarcinoma cells NIH:OVCAR-3, which over express A R. When these drugs are administered at therapeutic dose levels, a significant tumor growth arrest is observed.

  DOI：

  10.1021/jm9005803