hexadecyl uridin-5'-yl 2-([3R,4R]-3,4-dihydroxypyrrolidin-1-yl)ethylphosphonate | 1344121-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexadecyl uridin-5'-yl 2-([3R,4R]-3,4-dihydroxypyrrolidin-1-yl)ethylphosphonate
• 英文别名: hexadecyl uridin-5'-yl 2-([3R,4R]-3,4-dihydroxypyrrolidin-1-N-yl)ethylphosphonate；1-[(2R,3R,4S,5R)-5-[[2-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]ethyl-hexadecoxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1344121-83-0
• 化学式: C₃₁H₅₆N₃O₁₀P
• 分子量: 661.773
• InChiKey: CHGPVDHKMDQDQY-QBVQLYRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  45
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  178
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  ((3aR,4R,6R,6aR)-6-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl hexadecyl (2-((3R,4R)-3,4-dihydroxypyrrolidin-1-yl)ethyl)phosphonate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以590 mg的产率得到hexadecyl uridin-5'-yl 2-([3R,4R]-3,4-dihydroxypyrrolidin-1-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

文献信息

• Lipophosphonoxins, method of their preparation and use
  申请人：Ustav organicke chemie a biochemie AV CR, v.v.i.

  公开号：EP2527351B1

  公开（公告）日：2013-12-11
• Lipophosphonoxins: New Modular Molecular Structures with Significant Antibacterial Properties
  作者：Dominik Rejman、Alžbeta Rabatinová、António R. Pombinho、Soňa Kovačková、Radek Pohl、Eva Zbornı́ková、Milan Kolář、Kateřina Bogdanová、Otakar Nyč、Hana Šanderová、Tomáš Látal、Petr Bartůněk、Libor Krásný

  DOI：10.1021/jm2009343

  日期：2011.11.24

  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.