diethyl 3-(5-amino-4-carbamoyl-1H-1,2,3-triazol-1-yl)-2-hydroxypropylphosphonate | 1289220-68-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 3-(5-amino-4-carbamoyl-1H-1,2,3-triazol-1-yl)-2-hydroxypropylphosphonate
• 英文别名: diethyl 3-(5-amino-4-carbamoyl-1,2,3-triazol-1-yl)-2-hydroxypropylphosphonate；5-Amino-1-(3-diethoxyphosphoryl-2-hydroxypropyl)triazole-4-carboxamide
• CAS: 1289220-68-3
• 化学式: C₁₀H₂₀N₅O₅P
• 分子量: 321.273
• InChiKey: VDNLMVCNPKBZSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 3-(5-amino-4-carbamoyl-1H-1,2,3-triazol-1-yl)-2-hydroxypropylphosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到3-(5-amino-4-carbamoyl-1,2,3-triazol-1-yl)-2-hydroxypropylphosphonic acid
  参考文献：
  名称：

  Synthesis of Novel 1-Hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-Hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates

  摘要：

  Several new 1-hydroxy-2-(1,2,3-triazol-1-yl) ethylphosphonates and 2-hydroxy-3-(1,2,3-triazol-1-yl) propylphosphonates as well as the respective phosphonic acids were synthesized from diethyl 1,2-epoxyethylphosphonate and 2,3-epoxypropylphosphonate in the reaction sequence including the regioselective ring opening of the epoxide with azides followed by 1,3-dipolar cycloaddition of omega-azidophosphonates and selected alkynes and finally hydrolyses of the phosphonate esters.

  DOI：

  10.1080/10426507.2010.494646
• 作为产物：
  描述：

  2,3-环氧丙基膦酸二乙基酯 在 ammonium sulfate 、 sodium azide 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 9.5h， 生成 diethyl 3-(5-amino-4-carbamoyl-1H-1,2,3-triazol-1-yl)-2-hydroxypropylphosphonate
  参考文献：
  名称：

  Synthesis of Novel 1-Hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-Hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates

  摘要：

  Several new 1-hydroxy-2-(1,2,3-triazol-1-yl) ethylphosphonates and 2-hydroxy-3-(1,2,3-triazol-1-yl) propylphosphonates as well as the respective phosphonic acids were synthesized from diethyl 1,2-epoxyethylphosphonate and 2,3-epoxypropylphosphonate in the reaction sequence including the regioselective ring opening of the epoxide with azides followed by 1,3-dipolar cycloaddition of omega-azidophosphonates and selected alkynes and finally hydrolyses of the phosphonate esters.

  DOI：

  10.1080/10426507.2010.494646

文献信息

• Phosphonylated 8-Azahypoxantines as Acyclic Nucleotide Analogs
  作者：Anna Zdzienicka、Dominique Schols、Graciela Andrei、Robert Snoeck、Iwona E. Głowacka

  DOI：10.1080/10426507.2015.1054931

  日期：2015.12.2

  GRAPHICAL ABSTRACT Abstract A series of new phosphonylated 1,2,3-triazolo[4,5-d]pyrimidines (8-azahypoxanti-nes) was synthesized employing the 1,3-dipolar cycloaddition of corresponding ω-azidoalkylphosphonates and 2-cyanoacetamide followed by the pyrimidine ring closure with triethyl orthoformate. All compounds were evaluated in vitro for inhibitory activity against a broad variety of DNA and RNA

  图形摘要 摘要 使用相应的 ω-叠氮烷基膦酸酯和 2-氰基乙酰胺的 1,3-偶极环加成反应合成了一系列新的膦酰化 1,2,3-三唑并 [4,5-d] 嘧啶（8-氮杂环氧基乙酰胺）通过与原甲酸三乙酯的嘧啶环闭合。在体外评估了所有化合物对多种 DNA 和 RNA 病毒的抑制活性，但没有发现低于 100 μM 的活性。它们在 250 μM 时没有细胞抑制作用。
• Synthesis of Novel 1-Hydroxy-2-(1,2,3-triazol-1-yl)ethylphosphonates and 2-Hydroxy-3-(1,2,3-triazol-1-yl)propylphosphonates
  作者：Iwona E. Głowacka、Marcin Cieślak、Dorota G. Piotrowska

  DOI：10.1080/10426507.2010.494646

  日期：2011.2.28

  Several new 1-hydroxy-2-(1,2,3-triazol-1-yl) ethylphosphonates and 2-hydroxy-3-(1,2,3-triazol-1-yl) propylphosphonates as well as the respective phosphonic acids were synthesized from diethyl 1,2-epoxyethylphosphonate and 2,3-epoxypropylphosphonate in the reaction sequence including the regioselective ring opening of the epoxide with azides followed by 1,3-dipolar cycloaddition of omega-azidophosphonates and selected alkynes and finally hydrolyses of the phosphonate esters.