3,3-二(氨乙基)-1-羟基-2-羰基-1-三氮烯 | 146724-94-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3,3-二(氨乙基)-1-羟基-2-羰基-1-三氮烯
• 英文名称: NOC-18
• 英文别名: (z)-1-[2-(2-aminoethyl)-N-(2-ammonioethyl)amino] diazen-1-ium-1,2 diolate；(z)-1-[N-(2-aminoethyl)-N-(2-ammonioethyl)amino]diazen-1-ium-1,2-diolate；1-[N-(2-aminoethyl)-N-(2-ammonioethyl)-amino]-diazen-1-ium-1,2-diolate；3,3-bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene；(2,2'-hydroxynitrosohydrazino)-bis-ethanamine；2,2'-(hydroxynitrosohydrazino)bis-ethanamine；N-[bis(2-aminoethyl)amino]-N-hydroxynitrous amide
• CAS: 146724-94-9
• 化学式: C₄H₁₃N₅O₂
• mdl: MFCD00210194
• 分子量: 163.18
• InChiKey: HMRRJTFDJAVRMR-UHFFFAOYSA-N

物化性质

• 熔点：
  98-106 °C
• 沸点：
  290.26°C (rough estimate)
• 密度：
  1.3102 (rough estimate)
• 溶解度：
  H2O: >20 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -2.14
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108.18
• 氢给体数：
  3.0
• 氢受体数：
  6.0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2928000090

制备方法与用途

生物活性

NOC 18 是一种一氧化氮供体，在培养的大鼠小脑颗粒细胞中激活内向电流。它还能增加血管平滑肌细胞中的 cGMP 生成，并降低体外心肌制剂的收缩性。

用途

NOC 18 是一个稳定的亚胺类一氧化氮供体，能在生理条件下自发释放一氧化氮。在 pH7.4 的 0.1 M PBS 缓冲液中于 37℃ 下，0.1 mM NOC 5 的一氧化氮释放半衰期为 21 小时。

反应信息

• 作为反应物：
  描述：

  3,3-二(氨乙基)-1-羟基-2-羰基-1-三氮烯 在 高氯酸 作用下， 以 水 为溶剂， 生成 氧化亚氮 、 二乙烯三胺
  参考文献：
  名称：

  Decomposition of amino diazeniumdiolates (NONOates): Molecular mechanisms

  摘要：

  Although diazeniumdiolates (X[N(O)NO](-)) are extensively used in biochemical, physiological, and pharmacological studies due to their ability to release NO and/or its congeneric nitroxyl, the mechanisms of these processes remain obscure. In this work, we used a combination of spectroscopic, kinetic, and computational techniques to arrive at a quantitatively consistent molecular mechanism for decomposition of amino diazeniumdiolates (amino NONOates: R2N[N(O)NO](-), where R=N(C2H5)2 (1), N(C3H4NH2)2 (2), or N(C2H4NH2)2 (3)). Decomposition of these NONOates is triggered by protonation of their [NN(O)NO](-) group with the apparent pKa and decomposition rate constants of 4.6 and 1 s(-1) for 1; 3.5 and 0.083 s(-1) for 2; and 3.8 and 0.0033 s(-1) for 3. Although protonation occurs mainly on the O atoms of the functional group, only the minor R2N(H)N(O)NO tautomer (population ~10(-7), for 1) undergoes the NN heterolytic bond cleavage (kd~10(7) s(-1) for 1) leading to amine and NO. Decompositions of protonated amino NONOates are strongly temperature-dependent; activation enthalpies are 20.4 and 19.4 kcal/mol for 1 and 2, respectively, which includes contributions from both the tautomerization and bond cleavage. The bond cleavage rates exhibit exceptional sensitivity to the nature of R substituents which strongly modulate activation entropy. At pH<2, decompositions of all three NONOates that have been investigated are subject to additional acid catalysis that occurs through di-protonation of the [NN(O)NO](-) group.

  DOI：

  10.1016/j.jinorgbio.2014.08.008
• 作为产物：
  描述：

  二乙烯三胺 在 氧化亚氮 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 3,3-二(氨乙基)-1-羟基-2-羰基-1-三氮烯 、 双(2-氨基乙基)-N-亚硝胺
  参考文献：
  名称：

  Competitive Formation of N-Diazeniumdiolates and N-Nitrosamines via Anaerobic Reactions of Polyamines with Nitric Oxide

  摘要：

  Reactions of amines with nitric oxide (NO) at high pressures form diverse NO donor species, highly dependent on the precursor structure. While monoamine precursors favor the formation of N-diazeniumdiolates in high yield, polyamines exhibit competitive formation of N-nitrosamines and diazeniumdiolates, resulting in mixed products containing significant percentages of undesired N-nitroso compounds.

  DOI：

  10.1021/ol902282y

文献信息

• Assessment of oxidant stress in vitro and in vivo
  申请人：——

  公开号：US20020022244A1

  公开（公告）日：2002-02-21

  There is provided a method of assessing oxidant stress by measuring polymerization of proteins. Also provided is a marker for oxidant stress which includes a polymerized protein. A kit for use in assessing oxidant stress, the kit including an assay for detecting polymerized proteins is also provided. A method of lowering oxidant stress by administering to a patient an effective amount of at least one reducing agent is also provided. A pharmaceutical composition for lowering oxidant stress, the pharmaceutical having an effective amount of reducing agent and a pharmaceutically acceptable carrier is also provided.

  提供了一种通过测量蛋白质聚合来评估氧化应激的方法。还提供了一种氧化应激标记物，其中包括聚合的蛋白质。还提供了一种用于评估氧化应激的试剂盒，其中包括用于检测聚合蛋白质的试剂。还提供了一种通过向患者施用至少一种还原剂的有效剂量来降低氧化应激的方法。还提供了一种用于降低氧化应激的制药组合物，该制药组合物具有有效量的还原剂和药用可接受载体。
• Competitive Formation of <i>N</i>-Diazeniumdiolates and <i>N</i>-Nitrosamines via Anaerobic Reactions of Polyamines with Nitric Oxide
  作者：Peter N. Coneski、Mark H. Schoenfisch

  DOI：10.1021/ol902282y

  日期：2009.12.3

  Reactions of amines with nitric oxide (NO) at high pressures form diverse NO donor species, highly dependent on the precursor structure. While monoamine precursors favor the formation of N-diazeniumdiolates in high yield, polyamines exhibit competitive formation of N-nitrosamines and diazeniumdiolates, resulting in mixed products containing significant percentages of undesired N-nitroso compounds.
• Decomposition of amino diazeniumdiolates (NONOates): Molecular mechanisms
  作者：Nizamuddin Shaikh、Marat Valiev、Sergei V. Lymar

  DOI：10.1016/j.jinorgbio.2014.08.008

  日期：2014.12

  Although diazeniumdiolates (X[N(O)NO](-)) are extensively used in biochemical, physiological, and pharmacological studies due to their ability to release NO and/or its congeneric nitroxyl, the mechanisms of these processes remain obscure. In this work, we used a combination of spectroscopic, kinetic, and computational techniques to arrive at a quantitatively consistent molecular mechanism for decomposition of amino diazeniumdiolates (amino NONOates: R2N[N(O)NO](-), where R=N(C2H5)2 (1), N(C3H4NH2)2 (2), or N(C2H4NH2)2 (3)). Decomposition of these NONOates is triggered by protonation of their [NN(O)NO](-) group with the apparent pKa and decomposition rate constants of 4.6 and 1 s(-1) for 1; 3.5 and 0.083 s(-1) for 2; and 3.8 and 0.0033 s(-1) for 3. Although protonation occurs mainly on the O atoms of the functional group, only the minor R2N(H)N(O)NO tautomer (population ~10(-7), for 1) undergoes the NN heterolytic bond cleavage (kd~10(7) s(-1) for 1) leading to amine and NO. Decompositions of protonated amino NONOates are strongly temperature-dependent; activation enthalpies are 20.4 and 19.4 kcal/mol for 1 and 2, respectively, which includes contributions from both the tautomerization and bond cleavage. The bond cleavage rates exhibit exceptional sensitivity to the nature of R substituents which strongly modulate activation entropy. At pH<2, decompositions of all three NONOates that have been investigated are subject to additional acid catalysis that occurs through di-protonation of the [NN(O)NO](-) group.