5-(5'-amino-5'-deoxy-β-D-thymidin-5'N-yl)-1-(4-chloro-3-trifluoromethylphenyl)tetrazole | 1352504-89-2

• 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: 5-(5'-amino-5'-deoxy-β-D-thymidin-5'N-yl)-1-(4-chloro-3-trifluoromethylphenyl)tetrazole
• 英文别名: 1-[(2R,4S,5R)-5-[[[1-[4-chloro-3-(trifluoromethyl)phenyl]tetrazol-5-yl]amino]methyl]-4-hydroxy-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5R)-5-[[[1-[4-chloro-3-(trifluoromethyl)phenyl]tetrazol-5-yl]amino]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1352504-89-2
• 化学式: C₁₈H₁₇ClF₃N₇O₄
• 分子量: 487.826
• InChiKey: CUQUYBGGVVOGIK-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-氯-3-三氟甲基硫氰酸苯酯 在 sodium azide 、 四丁基氟化铵 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-(5'-amino-5'-deoxy-β-D-thymidin-5'N-yl)-1-(4-chloro-3-trifluoromethylphenyl)tetrazole
  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