O,O'-di(3'-O-acetyl-α-D-thymidine-5'-yl) [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate | 1504578-46-4

• 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: O,O'-di(3'-O-acetyl-α-D-thymidine-5'-yl) [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate
• CAS: 1504578-46-4
• 化学式: C₃₄H₃₆F₆N₅O₁₄P
• 分子量: 883.649
• InChiKey: QMXUITOIJBDCMU-YBMGUYPWSA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  60.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  245.41
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  diammonium [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate 、 3'-O-acetyl-2'-deoxy-α-D-thymidine 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 12.0h， 以8%的产率得到O,O'-di(3'-O-acetyl-α-D-thymidine-5'-yl) [3,5-bis(trifluoromethyl)phenylaminocarbonyl]methylphosphonate
  参考文献：
  名称：

  Synthesis and biological properties of α-thymidine 5′-aryl phosphonates

  摘要：

  Diethyl(N-arylaminocarbonyl)methyl phosphonates have been obtained by the reaction of diethylphosphonoacetic acid imidazolides with methyl-4-aminobenzoate or 3,5-bis(trifluoromethyl)phenylamine. Their treatment with Me3SiBr in DMF led to a mixture of the corresponding (N-arylaminocarbonylmethyl)phosphonic acids and their monoethyl esters. After separation, they were condensed with 3'-O-acetyl-alpha-thymidine, which, after the removal of the acetyl protecting group, gave (alpha-D-thymidine-5'-yl)-[4-aminocarbonyl-, methoxycarbonyl-, or carboxy)phenylaminocarbonyl]methyl phosphonates and (alpha-D-thymidine-5'-yl)-[3,5-bis(trifluoromethyl)phenylaminocarbonyl]methyl phosphonate and their ethyl esters. It was shown that the compounds are stable under different conditions, low toxic (in Vero and K-562 cell cultures), and capable of penetrating into K-562 cells. Only ethyl (alpha-D-thymidine-5'-yl)-[4-(methoxycarbonyl)phenylaminocarbonyl]methyl phosphonate at a high concentration (200 mu g/mL) inhibited in vitro the growth of the laboratory strain M. tuberculosis H37Rv.

  DOI：

  10.1134/s1068162013060058