O2-tetrahydropyran-2-yl 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate | 1037206-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: O2-tetrahydropyran-2-yl 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate
• 英文别名: JS-45-97；diethylamino-(oxan-2-yloxyimino)-oxidoazanium
• CAS: 1037206-77-1
• 化学式: C₉H₁₉N₃O₃
• 分子量: 217.268
• InChiKey: TWYWUVDEFJDBHU-UHFFFAOYSA-N

物化性质

• 沸点：
  301.8±52.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.13
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  sodium N,N-(diethylamino)diazen-1-ium-1,2-diolate 、 2-氯-四氢-2H-吡喃 在 15-冠醚-5 作用下， 以 环丁砜 为溶剂， 反应 1.0h， 生成 tetrahydro-2H-2-pyranol 、 O2-tetrahydropyran-2-yl 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  Hydrolytic Reactivity Trends among Potential Prodrugs of the O²-Glycosylated Diazeniumdiolate Family. Targeting Nitric Oxide to Macrophages for Antileishmanial Activity

  摘要：

  Glycosylated diazeniumdiolates of structure R(2)NN(O)=NO-R' (R' = a saccharide residue) are potential prodrugs of the nitric oxide (NO)-releasing but acid-sensitive R(2)NN(O)=NO(-) ion. Moreover, cleaving the acid-stable glycosides under alkaline conditions provides a convenient protecting group strategy for diazeniumdiolate ions. Here, we report comparative hydrolysis rate data for five representative glycosylated diazeniumdiolates at pH 14, 7.4, and 3.8-4.6 as background for further developing both the protecting group application and the ability to target NO pharmacologically to macrophages harboring intracellular pathogens. Confirming the potential in the latter application, adding R(2)NN(O)=NO-GlcNAc (where R(2)N = diethylamino or pyrrolidin-1-yl and GlcNAc = N-acetylglucosamin-1-yl) to cultures of infected mouse macrophages that were deficient in inducible NO synthase caused rapid death of the intracellular protozoan parasite Leishmania major with no host cell toxicity.

  DOI：

  10.1021/jm8000482

文献信息

• Hydrolytic Reactivity Trends among Potential Prodrugs of the O²-Glycosylated Diazeniumdiolate Family. Targeting Nitric Oxide to Macrophages for Antileishmanial Activity
  作者：Carlos A. Valdez、Joseph E. Saavedra、Brett M. Showalter、Keith M. Davies、Thomas C. Wilde、Michael L. Citro、Joseph J. Barchi、Jeffrey R. Deschamps、Damon Parrish、Stefan El-Gayar、Ulrike Schleicher、Christian Bogdan、Larry K. Keefer

  DOI：10.1021/jm8000482

  日期：2008.7

  Glycosylated diazeniumdiolates of structure R(2)NN(O)=NO-R' (R' = a saccharide residue) are potential prodrugs of the nitric oxide (NO)-releasing but acid-sensitive R(2)NN(O)=NO(-) ion. Moreover, cleaving the acid-stable glycosides under alkaline conditions provides a convenient protecting group strategy for diazeniumdiolate ions. Here, we report comparative hydrolysis rate data for five representative glycosylated diazeniumdiolates at pH 14, 7.4, and 3.8-4.6 as background for further developing both the protecting group application and the ability to target NO pharmacologically to macrophages harboring intracellular pathogens. Confirming the potential in the latter application, adding R(2)NN(O)=NO-GlcNAc (where R(2)N = diethylamino or pyrrolidin-1-yl and GlcNAc = N-acetylglucosamin-1-yl) to cultures of infected mouse macrophages that were deficient in inducible NO synthase caused rapid death of the intracellular protozoan parasite Leishmania major with no host cell toxicity.