2-pivaloylthioethyl 2',3'-isopropylideneuridin-5'-yl vinylphosphonate | 1344121-64-7

• 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: 2-pivaloylthioethyl 2',3'-isopropylideneuridin-5'-yl vinylphosphonate
• 英文别名: S-[2-[[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-ethenylphosphoryl]oxyethyl] 2,2-dimethylpropanethioate
• CAS: 1344121-64-7
• 化学式: C₂₁H₃₁N₂O₉PS
• 分子量: 518.525
• InChiKey: LNLDYGRMIXLDOO-KPEZKKAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-pivaloylthioethyl 2',3'-isopropylideneuridin-5'-yl vinylphosphonate 在 盐酸 作用下， 以 甲醇 、 正丁醇 为溶剂， 反应 12.0h， 生成 2-pivaloylthioethyl uridin-5'-yl 2-([3R,4R]-3,4-dihydroxypyrolidin-1-N-yl)ethylphosphonate
  参考文献：
  名称：

  Lipophosphonoxins: New Modular Molecular Structures with Significant Antibacterial Properties

  摘要：

  Novel compounds termed lipophosphonoxins were prepared using a simple and efficient synthetic approach. The general structure of lipophosphonoxins consists of four modules: (i) a nucleoside module, (ii) an iminosugar module, (iii) a hydrophobic module (lipophilic alkyl chain), and (iv) a phosphonate linker module that holds together modules i-iii. Lipophosphonoxins displayed significant antibacterial properties against a panel of Gram-positive species, including multiresistant strains. The minimum inhibitory concentration (MIC) values of the best inhibitors were in the 1-12 mu g/mL range, while their cytotoxic concentrations against human cell lines were significantly above this range. The modular nature of this artificial scaffold offers a large number of possibilities for further modifications/exploitation of these compounds.

  DOI：

  10.1021/jm2009343
• 作为产物：
  描述：

  、 S-(2-羟乙基)2,2-二甲基丙硫酸盐 在 2,4,6-三异丙基苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-pivaloylthioethyl 2',3'-isopropylideneuridin-5'-yl vinylphosphonate
  参考文献：
  名称：

  Lipophosphonoxins: New Modular Molecular Structures with Significant Antibacterial Properties

  摘要：

  Novel compounds termed lipophosphonoxins were prepared using a simple and efficient synthetic approach. The general structure of lipophosphonoxins consists of four modules: (i) a nucleoside module, (ii) an iminosugar module, (iii) a hydrophobic module (lipophilic alkyl chain), and (iv) a phosphonate linker module that holds together modules i-iii. Lipophosphonoxins displayed significant antibacterial properties against a panel of Gram-positive species, including multiresistant strains. The minimum inhibitory concentration (MIC) values of the best inhibitors were in the 1-12 mu g/mL range, while their cytotoxic concentrations against human cell lines were significantly above this range. The modular nature of this artificial scaffold offers a large number of possibilities for further modifications/exploitation of these compounds.

  DOI：

  10.1021/jm2009343