diethyl 6-(6-chloro-2,4-dimethoxypyrimidin-5-yl)-1-hexylphosphonate | 221133-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: diethyl 6-(6-chloro-2,4-dimethoxypyrimidin-5-yl)-1-hexylphosphonate
• 英文别名: 4-Chloro-5-(6-diethoxyphosphorylhexyl)-2,6-dimethoxypyrimidine
• CAS: 221133-21-7
• 化学式: C₁₆H₂₈ClN₂O₅P
• 分子量: 394.835
• InChiKey: AWMOVGGFMQGODJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 6-(6-chloro-2,4-dimethoxypyrimidin-5-yl)-1-hexylphosphonate 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以100%的产率得到6-(6-chloro-2,4-dihydroxypyrimidin-5-yl)-1-hexylphosphonic acid
  参考文献：
  名称：

  Design and synthesis of 6-(6-D-ribitylamino-2,4-dihydroxypyrimidin-5-yl)-1-hexylphosphonic acid, a potent inhibitor of lumazine synthase

  摘要：

  A novel inhibitor of lumazine synthase, the penulrimate enzyme in the biosynthesis of riboflavin, has been synthesized. The inhibitor was designed by computer graphics molecular modeling using a hypothetical structure of the enzyme-inhibitor complex. The new compound is relatively potent when compared with the known inhibitors, and displays a K-I of 109 mu M. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00687-8
• 作为产物：
  描述：

  1,6-二碘己烷 在 正丁基锂 、 sodium hydride 作用下， 反应 17.5h， 生成 diethyl 6-(6-chloro-2,4-dimethoxypyrimidin-5-yl)-1-hexylphosphonate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Homologous Phosphonic Acids and Sulfonic Acids as Inhibitors of Lumazine Synthase

  摘要：

  Three phosphonic acid inhibitors of lumazine synthase were synthesized in which the phosphorus atom was separated from the pyrimidinedione ring by polymethylene linker chains containing four, five, and six carbon atoms. Three analogous sulfonic acids were also synthesized. The inhibitors were designed as metabolically stable analogues of a hypothetical intermediate in the reaction catalyzed by lumazine synthase, and the design process was supported by the results of computer graphics molecular modeling of the inhibitors within the active site of the enzyme. The most potent of the new inhibitors, 6-(6-D-ribitylamino-2,4-dihydroxypyrimidine-5-yl)-1-hexylphosphonic acid, inhibited recombinant lumazine synthase beta(60) capsids of Bacillus subtilis with a K-i of 130 mu M, making it the most potent inhibitor of lumazine synthase reported to date.

  DOI：

  10.1021/jo9821729