5'-O-methanesulfonyl-4-thio-α-D-thymidine | 1352504-99-4

• 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: 5'-O-methanesulfonyl-4-thio-α-D-thymidine
• CAS: 1352504-99-4
• 化学式: C₁₁H₁₆N₂O₆S₂
• 分子量: 336.39
• InChiKey: RJYSAYKKHVWNNN-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110.62
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5'-O-methanesulfonyl-4-thio-α-D-thymidine 在 sodium azide 、 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
• 作为产物：
  描述：

  在 吡啶 、 甲醇 、 氨 作用下， 反应 5.0h， 生成 5'-O-methanesulfonyl-4-thio-α-D-thymidine
  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