4-[[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methylsulfanyl]-2,6-dimethoxy-5-nitropyrimidine | 952288-34-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-[[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methylsulfanyl]-2,6-dimethoxy-5-nitropyrimidine
• CAS: 952288-34-5
• 化学式: C₁₇H₂₅N₃O₈S
• 分子量: 431.467
• InChiKey: UDPSZTPUWLYCOK-JFGNBEQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-[[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methylsulfanyl]-2,6-dimethoxy-5-nitropyrimidine 在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以55%的产率得到5-nitro-6-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]sulfanyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Enzyme Inhibitory Activity of the S-Nucleoside Analogue of the Ribitylaminopyrimidine Substrate of Lumazine Synthase and Product of Riboflavin Synthase

  摘要：

  [GRAPHICS]Lumazine synthase and riboflavin synthase catalyze the last two steps in the biosynthesis of riboflavin. To obtain structural and mechanistic probes of these two enzymes, as well as inhibitors of potential value as antibiotics, a sulfur analogue of the pyrimidine substrate of the lumazine synthase-catalyzed reaction and product of the riboflavin synthase-catalyzed reaction was designed. Facile syntheses of the S-nucleoside 5-amino-6-(D-ribitylthio)pyrimidine-2,4(1H,3H)-dione hydrochloride (15) and its nitro precursor 5-nitro-6-(D-ribitylthio)pyrimidine-2,4(I H,3H)-dione (14) are described. These compounds were tested against lumazine synthase and riboflavin synthase obtained from a variety of microorganisms. Compounds 14 and 15 were found to be inhibitors of both riboflavin synthase and lumazine synthase. Compound 14 is an inhibitor of Bacillus subtilis lumazine synthase (K-i 26 mu M), Schizosaccharomyces pombe lumazine synthase (K-i 2.0 mu M), Mycobacterium tuberculosis lumazine synthase (K-i 11 mu M), Escherichia coli riboflavin synthase (K-i 2.7 mu M), and Mycobacterium tuberculosis riboflavin synthase (K-i 0.56 mu M), while compound 15 is an inhibitor of B. subtilis lumazine synthase (K-i 2.6 mu M), S. pombe lumazine synthase (K-i 0.16 mu M), M. tuberculosis lumazine synthase (K-i 31 mu M), E. coli riboflavin synthase (K-i 47 mu M), and M. tuberculosis riboflavin synthase (K-i 2.5 mu M).

  DOI：

  10.1021/jo0709495
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-1-O-toluene-p-sulphonyl-D-ribitol 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 15.0h， 生成 4-[[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methylsulfanyl]-2,6-dimethoxy-5-nitropyrimidine
  参考文献：
  名称：

  Synthesis and Enzyme Inhibitory Activity of the S-Nucleoside Analogue of the Ribitylaminopyrimidine Substrate of Lumazine Synthase and Product of Riboflavin Synthase

  摘要：

  [GRAPHICS]Lumazine synthase and riboflavin synthase catalyze the last two steps in the biosynthesis of riboflavin. To obtain structural and mechanistic probes of these two enzymes, as well as inhibitors of potential value as antibiotics, a sulfur analogue of the pyrimidine substrate of the lumazine synthase-catalyzed reaction and product of the riboflavin synthase-catalyzed reaction was designed. Facile syntheses of the S-nucleoside 5-amino-6-(D-ribitylthio)pyrimidine-2,4(1H,3H)-dione hydrochloride (15) and its nitro precursor 5-nitro-6-(D-ribitylthio)pyrimidine-2,4(I H,3H)-dione (14) are described. These compounds were tested against lumazine synthase and riboflavin synthase obtained from a variety of microorganisms. Compounds 14 and 15 were found to be inhibitors of both riboflavin synthase and lumazine synthase. Compound 14 is an inhibitor of Bacillus subtilis lumazine synthase (K-i 26 mu M), Schizosaccharomyces pombe lumazine synthase (K-i 2.0 mu M), Mycobacterium tuberculosis lumazine synthase (K-i 11 mu M), Escherichia coli riboflavin synthase (K-i 2.7 mu M), and Mycobacterium tuberculosis riboflavin synthase (K-i 0.56 mu M), while compound 15 is an inhibitor of B. subtilis lumazine synthase (K-i 2.6 mu M), S. pombe lumazine synthase (K-i 0.16 mu M), M. tuberculosis lumazine synthase (K-i 31 mu M), E. coli riboflavin synthase (K-i 47 mu M), and M. tuberculosis riboflavin synthase (K-i 2.5 mu M).

  DOI：

  10.1021/jo0709495