(Z)-1-[(2-aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (Z)-1-[(2-aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate
• 英文别名: 1-hydroxy-2-oxo-3,3-bis(2-aminoethyl)-1-triazene；NOC18；(1Z)-2,2-bis(2-aminoethyl)-1-(hydroxyimino)hydrazin-1-ium-1-olate；(E)-[bis(2-aminoethyl)amino]-hydroxyimino-oxidoazanium
• 化学式: C₄H₁₃N₅O₂
• 分子量: 163.18
• InChiKey: YNRCBOXEDICOIX-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二乙烯三胺 在 氧化亚氮 作用下， 以 乙腈 为溶剂， 反应 23.0h， 以90%的产率得到(Z)-1-[(2-aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  New nitric oxide-releasing zwitterions derived from polyamines

  摘要：

  The reaction of nitric oxide (NO) with polyamines has been studied, resulting in the discovery of a new type of NO-releasing compound having the structure RN[N(O)NO]-(CH2)xNH2+R' (3). Numerous examples of these zwitterionic polyamine/NO adducts have been prepared and found to be very stable solids which release NO in solution. The new compounds contain as much as 45% NO by weight and are capable of releasing it all at rates which have been shown to vary in a predictable way with structure. The half-lives in buffered aqueous solution at pH 7.4 and 22-degrees-C were shown to vary from extremely short (1.3 min for diamine 8, MeN[N(O)NO]-(CH2)4NH2+Me) to very long (56 h for triamine 18, H2NCH2CH2N[N(O)NO]-CH2CH2NH3+). In general, the longest half-lives were achieved by triamine/NO adducts and derivatives of ethylenediamine (x = 2). For any given value of x, a small increase in the size of R resulted in a relatively large increase in half-life but changes in R' appeared to have little effect. Data are presented which should allow the selection of the proper compounds to achieve a wide range of desired NO generation rates. These NO-containing zwitterions should prove to be important resources in studies of the biology of NO and may also have important pharmaceutical and chemical applications.

  DOI：

  10.1021/jo00058a030

文献信息

• New nitric oxide-releasing zwitterions derived from polyamines
  作者：Joseph A. Hrabie、John R. Klose、David A. Wink、Larry K. Keefer

  DOI：10.1021/jo00058a030

  日期：1993.3

  The reaction of nitric oxide (NO) with polyamines has been studied, resulting in the discovery of a new type of NO-releasing compound having the structure RN[N(O)NO]-(CH2)xNH2+R' (3). Numerous examples of these zwitterionic polyamine/NO adducts have been prepared and found to be very stable solids which release NO in solution. The new compounds contain as much as 45% NO by weight and are capable of releasing it all at rates which have been shown to vary in a predictable way with structure. The half-lives in buffered aqueous solution at pH 7.4 and 22-degrees-C were shown to vary from extremely short (1.3 min for diamine 8, MeN[N(O)NO]-(CH2)4NH2+Me) to very long (56 h for triamine 18, H2NCH2CH2N[N(O)NO]-CH2CH2NH3+). In general, the longest half-lives were achieved by triamine/NO adducts and derivatives of ethylenediamine (x = 2). For any given value of x, a small increase in the size of R resulted in a relatively large increase in half-life but changes in R' appeared to have little effect. Data are presented which should allow the selection of the proper compounds to achieve a wide range of desired NO generation rates. These NO-containing zwitterions should prove to be important resources in studies of the biology of NO and may also have important pharmaceutical and chemical applications.