JS-33-164 | 1037206-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: JS-33-164
• 英文别名: O2-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl) 1-(N,N-dimethylamino)diazen-1-ium-1,2-diolate
• CAS: 1037206-50-0
• 化学式: C₁₄H₂₃N₃O₉
• 分子量: 377.351
• InChiKey: NUVNOOVSPGJPSI-AJVHJNHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  139.03
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-hydroxy-3,3-dimethyltriaz-1-ene 2-oxide sodium salt 、 2,3,4-三-O-乙酰基-6-脱氧-alpha-L-溴代半乳糖 在 碳酸氢钠 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 以2.2 g的产率得到JS-33-164
  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