(-)-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)-5-iodouracil | 1620879-48-2

• 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: (-)-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)-5-iodouracil
• CAS: 1620879-48-2
• 化学式: C₉H₁₀IN₅O₄Se
• 分子量: 458.074
• InChiKey: NLLAARADYSGCSG-BYPJNBLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  144.08
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (-)-1-(4-seleno-D-ribofuranosyl)-5-iodouracil 在 吡啶 、 叠氮磷酸二苯酯 、 四丁基溴化铵 、 氨 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 (-)-1-(2-azido-2-deoxy-4-seleno-D-arabinofuranosyl)-5-iodouracil
  参考文献：
  名称：

  Structure–activity relationships of 2′-modified-4′-selenoarabinofuranosyl-pyrimidines as anticancer agents

  摘要：

  Based on the potent anticancer activity of the D-arabino-configured cytosine nucleoside ara-C, novel 2'-substituted-4'-selenoarabinofuranosyl pyrimidines 3a-3u, comprising azido, fluoro, and hydroxyl substituents at C-2' were designed, synthesized, and evaluated for anticancer activity. The 2'-azido group was stereoselectively introduced by the Mitsunobu reaction using diphenylphosphoryl azide (DPPA), and the 2'-fluoro group was stereoselectively introduced through the double inversions of stereochemistry via the episelenium intermediate, which was formed by the participation of the selenium atom. Among the compounds tested, the 2'-fluoro derivative 3t (X = NH2, Y = H, R = F) was found to be the most potent anticancer agent and showed more potent anticancer activity than the control, ara-C in all tested human cancer cell lines (HCT116, A549, SNU638, T47D, and PC-3) except the leukemia cell lines (K562). The anticancer activity of the 2'-substituted-4'-selenonucleosides is in the following order: 2'-F > 2'-OH > 2'-N3.

  DOI：

  10.1016/j.ejmech.2014.06.031