ethyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-propan-2-yloxyphosphinothioyl]amino]-3-methylbutanoate | 1429327-12-7

• 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: ethyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-propan-2-yloxyphosphinothioyl]amino]-3-methylbutanoate
• CAS: 1429327-12-7
• 化学式: C₂₀H₃₃N₆O₇PS
• 分子量: 532.558
• InChiKey: ZKQXSKIEERLRBD-GNADUKHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  L-缬氨酸乙酯盐酸盐 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 ethyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-propan-2-yloxyphosphinothioyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  Synthesis of Novel Nucleoside Analogue Phosphorothioamidate Prodrugs and in vitro Anticancer Evaluation Against RKO Human Colon Carcinoma Cells

  摘要：

  Novel phosphorothioamidates of pyrimidine nucleoside analogues have been prepared and evaluated in vitro against RKO human colon cancer cell by the MTT cytotoxicity assay. The parent nucleoside analogues were inactive in this assay, while the phosphorothioamidate prodrugs were active at low uM levels in some cases. The O-isopropyl phosphorothioamidate of 2,3-O-isopropylidene-uridine containing the L-phenylalanine ethyl ester 6f was the most active at 148 uM, a 10-fold enhancement in anticancer activity compared with the parent nucleoside 2 with no increase in cytotoxicity.

  DOI：

  10.1080/15257770.2013.770523