diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]prop-1-ynylphosphonate | 939387-56-1

• 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]prop-1-ynylphosphonate
• 英文别名: diethyl 3-(N-benzyloxy,N-(2-nitrobenzenesulfonyl)amino)-propynyl phosphonate；Diethyl 3-[N-benzyloxy,N-(2-nitrobenzenesulfonyl)amino]-propynylphosphonate；N-(3-diethoxyphosphorylprop-2-ynyl)-2-nitro-N-phenylmethoxybenzenesulfonamide
• CAS: 939387-56-1
• 化学式: C₂₀H₂₃N₂O₈PS
• 分子量: 482.451
• InChiKey: NEUDYFFCQIQNEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]prop-1-ynylphosphonate 在 四(三苯基膦)钯 三正丁基氢锡 、 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 3.0h， 生成 diethyl (Z)-3-[N-acetyl-N-(benzyloxy)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
• 作为产物：
  描述：

  diethyl (3-(tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-ylphosphonate 在 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 20.0h， 生成 diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]prop-1-ynylphosphonate
  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

• Organophosphoric Derivatives Useful as Anti-Parasitic Agents
  申请人：Van Calenbergh Serge

  公开号：US20080312190A1

  公开（公告）日：2008-12-18

  The present invention relates to novel phosphonic acid compounds having the structural formula (I): wherein: (a) R is a group of 1 to 5 substituents independently selected from the group consisting of fluoro, chloro, bromo, C 1-4 alkoxy, C 1-4 alkyl, hydroxy, formyl, trifluoromethoxy, phenyl, heterocyclic, heterocyclic-substituted methyl, aminomethyl, hydroxy methyl, bromomethyl, sulfonyl chloride, acetyl chloride, nitroso and cyano, (b) R 1 is selected from the group consisting of hydrogen, C 1-7 alkyl, C 3-10 cycloalkyl, aryl, arylalkyl and heterocyclic, and (c) R 2 is selected from the group consisting of hydroxy and hydroxy-protecting groups, and stereoisomer, solvates and salts thereof. These compounds are useful as anti-infectious and anti-parasitic agents, in particular anti-malaria agents.

  本发明涉及具有结构式(I)的新型膦酸化合物，其中：(a) R是1至5个取代基的基团，这些取代基独立地选自于氟、氯、溴、C1-4烷氧基、C1-4烷基、羟基、甲酰基、三氟甲氧基、苯基、杂环、杂环取代的甲基、氨甲基、羟甲基、溴甲基、磺酰氯、乙酰氯、亚硝基和氰基；(b) R1选自于氢、C1-7烷基、C3-10环烷基、芳基、芳基烷基和杂环；(c) R2选自于羟基和羟基保护基团，以及其立体异构体、溶剂化物和盐。这些化合物可用作抗感染和抗寄生虫剂，特别是抗疟疾剂。
• Organophosphoric derivatives useful as anti-parasitic agents
  申请人：Universiteit Gent

  公开号：US07638505B2

  公开（公告）日：2009-12-29

  The present invention relates to novel phosphonic acid compounds having the structural formula (I): wherein: (a) R is a group of 1 to 5 substituents independently selected from the group consisting of fluoro, chloro, bromo, C1-4 alkoxy, C1-4 alkyl, hydroxy, formyl, trifluoromethoxy, phenyl, heterocyclic, heterocyclic-substituted methyl, aminomethyl, hydroxy methyl, bromomethyl, sulfonyl chloride, acetyl chloride, nitroso and cyano, (b) R1 is selected from the group consisting of hydrogen, C1-7 alkyl, C3-10 cycloalkyl, aryl, arylalkyl and heterocyclic, and (c) R2 is selected from the group consisting of hydroxy and hydroxy-protecting groups, and stereoisomer, solvates and salts thereof. These compounds are useful as anti-infectious and anti-parasitic agents, in particular anti-malaria agents.

  本发明涉及具有结构式（I）的新型膦酸化合物，其中：（a）R是1至5个取代基的基团，所述取代基独立地选自以下组成的群体：氟、氯、溴、C1-4烷氧基、C1-4烷基、羟基、甲酰基、三氟甲氧基、苯基、杂环、杂环取代甲基、氨基甲基、羟甲基、溴甲基、磺酰氯、乙酰氯、亚硝基和氰基；（b）R1选自以下组成的群体：氢、C1-7烷基、C3-10环烷基、芳基、芳基烷基和杂环；（c）R2选自以下组成的群体：羟基和羟基保护基，以及其立体异构体、溶剂化合物和盐。这些化合物可用作抗感染和抗寄生虫剂，特别是抗疟疾剂。
• WO2007/71453
  申请人：——

  公开号：——

  公开（公告）日：——
• US7638505B2
  申请人：——

  公开号：US7638505B2

  公开（公告）日：2009-12-29