5'-脱氧-5'-[4-(4-氟苯基)-(1,2,3)三唑-1-基]胸苷 | 1046354-53-3

• 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
• 中文名称: 5'-脱氧-5'-[4-(4-氟苯基)-(1,2,3)三唑-1-基]胸苷
• 英文名称: 5'-deoxy-5'-[4-(4-fluorophenyl)-(1,2,3)triazol-1-yl]thymidine
• 英文别名: 1-[(2R,4S,5R)-5-[[4-(4-fluorophenyl)triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1046354-53-3
• 化学式: C₁₈H₁₈FN₅O₄
• 分子量: 387.37
• InChiKey: GBMDCGNBZMCVQA-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氟苯乙炔 、 5-叠氮基-5-脱氧胸腺嘧啶脱氧核苷 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以13%的产率得到5'-脱氧-5'-[4-(4-氟苯基)-(1,2,3)三唑-1-基]胸苷
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Inhibitors of Thymidine Monophosphate Kinase fromBacillus Anthracis

  摘要：

  Nineteen lipophilic thymidine phosphate-mimicking compounds were designed and synthesized as potential inhibitors of thymidine monophosphate kinase of Bacillus anthracis, a Gram-positive bacterium that causes anthrax. These thymidine analogues were substituted at the 5'-postion with sulfonamide-, amide-, (thio)urea-, or triazole groups, which served as lipophilic surrogates for phosphate. Three of the tested compounds produced inhibition of B. anthracis Sterne growth and/or thymidine monophosphate activity. Additional studies will be necessary to elucidate the potential of this type of B. anthracis thymidine monophosphate inhibitors as novel antibiotics in the treatment Of anthrax.

  DOI：

  10.1080/15257770701845238

文献信息

• Synthesis and Biological Evaluation of Inhibitors of Thymidine Monophosphate Kinase from<i>Bacillus Anthracis</i>
  作者：Youngjoo Byun、Susan R. Vogel、Andrew J. Phipps、Cecilia Carnrot、Staffan Eriksson、Rohit Tiwari、Werner Tjarks

  DOI：10.1080/15257770701845238

  日期：2008.2.8

  Nineteen lipophilic thymidine phosphate-mimicking compounds were designed and synthesized as potential inhibitors of thymidine monophosphate kinase of Bacillus anthracis, a Gram-positive bacterium that causes anthrax. These thymidine analogues were substituted at the 5'-postion with sulfonamide-, amide-, (thio)urea-, or triazole groups, which served as lipophilic surrogates for phosphate. Three of the tested compounds produced inhibition of B. anthracis Sterne growth and/or thymidine monophosphate activity. Additional studies will be necessary to elucidate the potential of this type of B. anthracis thymidine monophosphate inhibitors as novel antibiotics in the treatment Of anthrax.