[(2S,3S,4R,5R)-3-amino-4-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [(2S,3S,4R,5R)-3-amino-4-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
• 英文别名: [(2S,3S,4R,5R)-3-amino-4-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
• 化学式: C₁₀H₁₆N₃O₈P
• 分子量: 337.226
• InChiKey: BOECYGFZFFYWPU-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 吡啶 、 磷酸三甲酯 、 ammonium hydroxide 、 Me₃SiOSO₃CF₃ 、 三苯基膦 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 [(2S,3S,4R,5R)-3-amino-4-hydroxy-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase

  摘要：

  A number of 2'- and 3'-modified thymidine 5'-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2'-halogeno substituent and a 3'-azido function are the most favorable leads for further development of potent inhibitors of this enzyme. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00551-6

文献信息

• Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase
  作者：Veerle Vanheusden、Hélène Munier-Lehmann、Sylvie Pochet、Piet Herdewijn、Serge Van Calenbergh

  DOI：10.1016/s0960-894x(02)00551-6

  日期：2002.10

  A number of 2'- and 3'-modified thymidine 5'-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2'-halogeno substituent and a 3'-azido function are the most favorable leads for further development of potent inhibitors of this enzyme. (C) 2002 Elsevier Science Ltd. All rights reserved.