diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]-1-(4-nitrophenyl)prop-1-enylphosphonate | 939387-86-7

• 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: diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]-1-(4-nitrophenyl)prop-1-enylphosphonate
• 英文别名: diethyl (Z)-3-(N-benzyloxy,N-(2-nitrobenzenesulfonyl)amino)-1-(4-nitrophenyl)-propenylphosphonate；N-[(Z)-3-diethoxyphosphoryl-3-(4-nitrophenyl)prop-2-enyl]-2-nitro-N-phenylmethoxybenzenesulfonamide
• CAS: 939387-86-7
• 化学式: C₂₆H₂₈N₃O₁₀PS
• 分子量: 605.562
• InChiKey: QJBXRNMHDHYVOR-BWAHOGKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]-1-(4-nitrophenyl)prop-1-enylphosphonate 在 palladium on activated charcoal 三甲基溴硅烷 、 氢气 、 sodium carbonate 、 potassium carbonate 、 二甲基亚砜 、 苯硫酚 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 48.0h， 生成 3-[N-acetyl-N-(hydroxy)amino]-1-(4-aminophenyl)propylphosphonic acid
  参考文献：
  名称：

  Divergent Strategy for the Synthesis of α-Aryl-Substituted Fosmidomycin Analogues

  摘要：

  [GRAPHICS]Fosmidomycin is the first representative of a new class of antimalarial drugs acting through inhibition of 1-deoxy-D-xylulose 5-phosphate ( DOXP) reductoisomerase (DXR), an essential enzyme in the non-mevalonate pathway for the synthesis of isoprenoids. This work describes a divergent strategy for the synthesis of a series of alpha-aryl-substituted fosmidomycin analogues, featuring a palladium-catalyzed Stille coupling as the key step. An alpha-(4-cyanophenyl)fosmidomycin analogue emerged as the most potent analogue in the present series. Its antimalarial activity clearly surpasses that of the reference compound fosmidomycin.

  DOI：

  10.1021/jo0700981
• 作为产物：
  描述：

  diethyl (3-(tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-ylphosphonate 在 四(三苯基膦)钯 三正丁基氢锡 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 23.0h， 生成 diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]-1-(4-nitrophenyl)prop-1-enylphosphonate
  参考文献：
  名称：

  Divergent Strategy for the Synthesis of α-Aryl-Substituted Fosmidomycin Analogues

  摘要：

  [GRAPHICS]Fosmidomycin is the first representative of a new class of antimalarial drugs acting through inhibition of 1-deoxy-D-xylulose 5-phosphate ( DOXP) reductoisomerase (DXR), an essential enzyme in the non-mevalonate pathway for the synthesis of isoprenoids. This work describes a divergent strategy for the synthesis of a series of alpha-aryl-substituted fosmidomycin analogues, featuring a palladium-catalyzed Stille coupling as the key step. An alpha-(4-cyanophenyl)fosmidomycin analogue emerged as the most potent analogue in the present series. Its antimalarial activity clearly surpasses that of the reference compound fosmidomycin.

  DOI：

  10.1021/jo0700981

文献信息

• WO2007/71453
  申请人：——

  公开号：——

  公开（公告）日：——