<(82)Br>-5-bromo-1-(2-fluoro-2-deoxy-β-D-ribofuranosyl)uracil | 120332-43-6

• 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: <(82)Br>-5-bromo-1-(2-fluoro-2-deoxy-β-D-ribofuranosyl)uracil
• CAS: 120332-43-6
• 化学式: C₉H₁₀BrFN₂O₅
• 分子量: 327.187
• InChiKey: WFOXFPXBLFRFHB-USWITIRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  104.55
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5-bromo-1-(2-fluoro-2-deoxy-β-D-ribofuranosyl)uracil 在 N-氯代丁二酰亚胺 、 <82Br>NH4Br 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以57%的产率得到<(82)Br>-5-bromo-1-(2-fluoro-2-deoxy-β-D-ribofuranosyl)uracil
  参考文献：
  名称：

  Synthesis and tumor uptake of 5-bromine-82- and 5-iodine-131-labeled 5-halo-1-(2-fluoro-2-deoxy-.beta.-D-ribofuranosyl)uracils

  摘要：

  A synthesis of 5-bromo- and 5-iodo-1-(2-fluoro-2-deoxy-beta-D-ribofuranosyl)uracil (3 and 4) and their 5-82Br and 5-131I analogues has been developed. The tissue distribution of the radiolabeled compounds in BDF1 mice bearing Lewis lung tumors has been investigated. After injection of the radiolabeled analogues of compounds 3 and 4 there was a rapid initial excretion of activity. Compound 3 was excreted unchanged in the urine. Residual activity in mice after 4 h showed a distribution characteristic of bromide (Br-). Compound 4 was excreted mainly as unchanged starting material with increasing amounts of iodide (I-) detected at later time periods, in addition to 5-iodouridine and unidentified metabolites at shorter time periods. Both 3 and 4 demonstrated a remarkable in vivo stability relative to related 5-substituted nucleosides that do not contain the 2'-fluoro group. The tumor uptake was minimal, with only the 5-bromo analogue demonstrating a slight elevation in tumor to blood ratios relative to other tissues. Compounds 3 and 4 were shown to compete with thymidine for the same binding site in the transport of nucleosides across the cell membrane in mouse erythrocytes. The inhibition constants (Ki) show that the compounds were weak competitors of thymidine binding to pyrimidine nucleoside transporter compared to physiological nucleosides. Other evidence indicates that compounds 3 and 4 are not substrates for mammalian kinase enzymes.

  DOI：

  10.1021/jm00126a024

文献信息

• MERCER, JOHN R.;XU, LI-HUA;KNAUS, EDWARD E.;WIEBE, LEONARD I., J. MED. CHEM., 32,(1989) N, C. 1289-1294
  作者：MERCER, JOHN R.、XU, LI-HUA、KNAUS, EDWARD E.、WIEBE, LEONARD I.

  DOI：——

  日期：——