((3aR,4R,6R,6aR)-6-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (3-(hexadecyloxy)propyl) (2-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)ethyl)phosphonate | 1414873-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((3aR,4R,6R,6aR)-6-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (3-(hexadecyloxy)propyl) (2-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)ethyl)phosphonate
• CAS: 1414873-40-7
• 化学式: C₄₄H₇₁N₄O₁₁P
• 分子量: 863.042
• InChiKey: DNWIXPQCKLRIME-RHHBSAIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  60.0
• 可旋转键数：
  29.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  180.14
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  ((3aR,4R,6R,6aR)-6-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (3-(hexadecyloxy)propyl) (2-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)ethyl)phosphonate 在 盐酸 、 甲胺 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 3-(hexadecyloxy)propyl cytidin-5'-yl 2-([3R,4R]-3,4-dihydroxypyrrolidin-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：

  4-N-benzoyl-2',3'-isopropylidenecytidin-5'-yl vinylphosphonate 在 2,4,6-三异丙基苯磺酰氯 作用下， 以 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 12.17h， 生成 ((3aR,4R,6R,6aR)-6-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (3-(hexadecyloxy)propyl) (2-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)ethyl)phosphonate
  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