O2-(β-L-fucopyranosyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate | 1037206-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O2-(β-L-fucopyranosyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate
• 英文别名: JS-33-177
• CAS: 1037206-55-5
• 化学式: C₈H₁₇N₃O₆
• 分子量: 251.239
• InChiKey: UQNIHNLHZLWBTB-FMGWEMOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.82
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  120.82
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  JS-33-164 在 甲醇 、 sodium methylate 作用下， 生成 O2-(β-L-fucopyranosyl) 1-(N,N-dimethylamino)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