5-fuoro-5'-(1-pyrenylbutanoate)-2'-deoxyuridine | 1360194-80-4

• 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-fuoro-5'-(1-pyrenylbutanoate)-2'-deoxyuridine
• CAS: 1360194-80-4
• 化学式: C₂₉H₂₅FN₂O₆
• 分子量: 516.526
• InChiKey: OSDJUZHNBLIJHY-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  110.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以267 mg的产率得到5-fuoro-5'-(1-pyrenylbutanoate)-2'-deoxyuridine
  参考文献：
  名称：

  Delivery of Floxuridine Derivatives to Cancer Cells by Water-Soluble Organometallic Cages

  摘要：

  The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene (pPr(i)C(6)H(4)Me) ruthenium building blocks and 2,5-dioxydo-1,4-benzoquinonato (dobq) or 5,8-dioxydo-1,4-naphthoquinonato (donq) bridges, in the presence of a pyrenyl-nucleoside derivatives (pyreneR),. affords the triangular prismatic host guest compounds [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(dobq)(3)](6+) ([(pyrene-R)C1](6+)) and [(pyrene-R)CRu6(pPr(i)C(6)H(4)Me)(6)(tpt)(2)(donq)(3)](6+) ([(pyrene-R)C2](6+)), respectively. The inclusion of six monosubstituted pyrenyl-nucleosides (pyrene-R1 = 5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R2 = 5-fluoro-5'-(1-pyrenyl butanoate)-2'-deoxyuridine, pyrene-R3 = 5'-{N-[1-oxo-4-(1-pyrenyl)butyl]glycyl}-2'-deoxyuridine, pyrene-R4 = 5-fluoro-5'-{N[1-oxo-4-(1-pyrenyl)butyl]-glycyl}2'-deoxyuridine, pyrene-R5 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyvuridine, pyrene-R6 = 5-fluoro-5'-{N-[1-oxo-4-(1-pyrenyl)butyl]-phenylalanyl}-2'-deoxyuridine) has been accomplished. The carceplex nature of [(pyrene-R)C1](6+) with the pyrenyl moiety firmly encapsulated in the hydrophobic cavity of the cage with the nucleoside groups pointing outward was confirmed by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), while the host-guest nature of [(pyrene-R)C2](6+) was studied in solution by NMR techniques. In contrast to the floxuridine compounds used in the clinic, the host-guest complexes are highly water-soluble. Consequently, the cytotoxicities of these water-soluble compounds have been established using human ovarian A2780 and A2780cisR cancer cells. All the host guest systems are more cytotoxic than the empty cages alone [1][CF3SO3](6) (IC50 = 23 mu M) and [2][CF3SO3](6) (IC50 = 10 mu M), the most active compound [pyrene-R4C1][CF3SO3](6) being 2 orders of magnitude more cytotoxic (IC50 = 0.3 mu M) on these human ovarian cancer cell lines (A2780 and A2780cisR).

  DOI：

  10.1021/bc200472n