N-(5'-deoxy-4-thio-α-D-thymidin-5'-yl)-N'-(3-trifluoromethyl-4-chlorophenyl)thiourea | 1352505-05-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: N-(5'-deoxy-4-thio-α-D-thymidin-5'-yl)-N'-(3-trifluoromethyl-4-chlorophenyl)thiourea
• 英文别名: 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[[(2R,3S,5S)-3-hydroxy-5-(5-methyl-2-oxo-4-thioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl]thiourea；1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[[(2R,3S,5S)-3-hydroxy-5-(5-methyl-2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl]thiourea
• CAS: 1352505-05-5
• 化学式: C₁₈H₁₈ClF₃N₄O₃S₂
• 分子量: 494.946
• InChiKey: ZOSAVGSYBNMSTG-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5'-azido-5'-deoxy-4-thio-α-D-thymidine 在 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.17h， 生成 N-(5'-deoxy-4-thio-α-D-thymidin-5'-yl)-N'-(3-trifluoromethyl-4-chlorophenyl)thiourea
  参考文献：
  名称：

  Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase

  摘要：

  We report on Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) inhibitory activities of a series of new 3'- and 5'-modified thymidine analogues including alpha- and beta-derivatives. In addition, several analogues were synthesized in which the 4-oxygen was replaced by a more lipophilic sulfur atom to probe the influence of this modification on TMPKmt inhibitory activity. Several compounds showed an inhibitory potency in the low micromolar range, with the 5'-arylthiourea 4-thio-alpha-thymidine analogue being the most active one (K(i) = 0.17 mu M). This compound was capable of inhibiting mycobacteria growth at a concentration of 25 mu g/mL. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.021