N-(5'-deoxy-3'-O-tert-butyldimethylsilyl-β-D-thymidin-5'-yl)-N'-(4-chloro-3-trifluoromethylphenyl)thiourea | 1352504-84-7

• 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-3'-O-tert-butyldimethylsilyl-β-D-thymidin-5'-yl)-N'-(4-chloro-3-trifluoromethylphenyl)thiourea
• CAS: 1352504-84-7
• 化学式: C₂₄H₃₂ClF₃N₄O₄SSi
• 分子量: 593.142
• InChiKey: GBMFDCZYIRJUBD-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  97.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(5'-deoxy-3'-O-tert-butyldimethylsilyl-β-D-thymidin-5'-yl)-N'-(4-chloro-3-trifluoromethylphenyl)thiourea 在 sodium azide 、 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到5-(5'-amino-5'-deoxy-3'-O-tert-butyldimethylsilyl-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
• 作为产物：
  描述：

  4-氯-3-三氟甲基硫氰酸苯酯 、 5'-amino-3'-tert-butyldimethylsilyl-5'-deoxythymidine 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以76%的产率得到N-(5'-deoxy-3'-O-tert-butyldimethylsilyl-β-D-thymidin-5'-yl)-N'-(4-chloro-3-trifluoromethylphenyl)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