O2-(2-methoxyaminosulfonylethyl) 1-(isopropylamino)-diazen-1-ium-1,2-diolate | 1404220-14-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: O2-(2-methoxyaminosulfonylethyl) 1-(isopropylamino)-diazen-1-ium-1,2-diolate
• 英文别名: [2-(Methoxysulfamoyl)ethoxyamino]-oxido-propan-2-yliminoazanium；[2-(methoxysulfamoyl)ethoxyamino]-oxido-propan-2-yliminoazanium
• CAS: 1404220-14-9
• 化学式: C₆H₁₆N₄O₅S
• 分子量: 256.283
• InChiKey: QDFJHOLZBMQRBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  O2-(2-acetylthioethyl) 1-(isopropylamino)diazen-1-ium-1,2-diolate 在 氯化亚砜 、 双氧水 、 sodium acetate 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 O2-(2-methoxyaminosulfonylethyl) 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

文献信息

• <i>O</i>²-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
  作者：Zhangjian Huang、Jatinder Kaur、Atul Bhardwaj、Nasser Alsaleh、Julie A. Reisz、Jenna F. DuMond、S. Bruce King、John M. Seubert、Yihua Zhang、Edward E. Knaus

  DOI：10.1021/jm301303p

  日期：2012.11.26

  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.