O2-(2-methylthioethyl) 1-(isopropylamino)diazen-1-ium-1,2-diolate | 1404220-31-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: O2-(2-methylthioethyl) 1-(isopropylamino)diazen-1-ium-1,2-diolate
• 英文别名: (2-Methylsulfanylethoxyamino)-oxido-propan-2-yliminoazanium；(2-methylsulfanylethoxyamino)-oxido-propan-2-yliminoazanium
• CAS: 1404220-31-0
• 化学式: C₆H₁₅N₃O₂S
• 分子量: 193.27
• InChiKey: JUUNGSSIUGZPRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O2-(2-methylthioethyl) 1-(isopropylamino)diazen-1-ium-1,2-diolate 在 oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以55%的产率得到O2-(2-methylsulfonylethyl) 1-(isopropylamino)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  O²-Sulfonylethyl Protected Isopropylamine Diazen-1-ium-1,2-diolates as Nitroxyl (HNO) Donors: Synthesis, β-Elimination Fragmentation, HNO Release, Positive Inotropic Properties, and Blood Pressure Lowering Studies

  摘要：

  New types of nonexplosive O-2-sulfonylethyl protected (-CH2CH2SO2R; R = OMe, NHOMe, NHOBn, Me) derivatives of isopropylamine diazen-1-ium-1,2-diolate (IPA/NO) (2-5) were developed that are designed to act as novel HNO donors. These compounds, with suitable half lives (6.6-17.1 h) at pH 7.4, undergo a base induced beta-elimination reaction that releases a methyl vinyl sulfone product and the, parent IPA/NO anion which subsequently preferentially releases HNO (46-61% range). Importantly, the O-2-methylsulfonylethyl compound 5 exhibited a significant in vitro inotropic effect up to 283% of the baseline value and increased the rates of contraction and relaxation but did not induce a chronotropic effect. Furthermore; compound 5 (22.5 mg/kg po dose). provided a significant reduction in blood pressure up to 6 h after drug administration. All these data suggest that O-2-sulfonylethyl protected derivatives of IPA/NO, which are efficient HNO donors, could have potential applications to treat cardiovascular disease(s) such as congestive heart failure.

  DOI：

  10.1021/jm301303p
• 作为产物：
  描述：

  isopropylammonium 1-(isopropylamino)diazen-1-ium-1,2-diolate 、 1-碘-2-甲硫基乙烷 在 15-冠醚-5 作用下， 以 甲醇 为溶剂， 反应 15.5h， 以27.8%的产率得到O2-(2-methylthioethyl) 1-(isopropylamino)diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  O²-Sulfonylethyl Protected Isopropylamine Diazen-1-ium-1,2-diolates as Nitroxyl (HNO) Donors: Synthesis, β-Elimination Fragmentation, HNO Release, Positive Inotropic Properties, and Blood Pressure Lowering Studies

  摘要：

  New types of nonexplosive O-2-sulfonylethyl protected (-CH2CH2SO2R; R = OMe, NHOMe, NHOBn, Me) derivatives of isopropylamine diazen-1-ium-1,2-diolate (IPA/NO) (2-5) were developed that are designed to act as novel HNO donors. These compounds, with suitable half lives (6.6-17.1 h) at pH 7.4, undergo a base induced beta-elimination reaction that releases a methyl vinyl sulfone product and the, parent IPA/NO anion which subsequently preferentially releases HNO (46-61% range). Importantly, the O-2-methylsulfonylethyl compound 5 exhibited a significant in vitro inotropic effect up to 283% of the baseline value and increased the rates of contraction and relaxation but did not induce a chronotropic effect. Furthermore; compound 5 (22.5 mg/kg po dose). provided a significant reduction in blood pressure up to 6 h after drug administration. All these data suggest that O-2-sulfonylethyl protected derivatives of IPA/NO, which are efficient HNO donors, could have potential applications to treat cardiovascular disease(s) such as congestive heart failure.

  DOI：

  10.1021/jm301303p