(2E)-2-[[(Z)-N'-nitrocarbamimidoyl]hydrazinylidene]acetic acid

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E)-2-[[(Z)-N'-nitrocarbamimidoyl]hydrazinylidene]acetic acid
• 化学式: C₃H₅N₅O₄
• 分子量: 175.104
• InChiKey: LPNFCWOBFPSPKN-ORCRQEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-2-[[(Z)-N'-nitrocarbamimidoyl]hydrazinylidene]acetic acid 以 氘代二甲亚砜 为溶剂， 反应 2.0h， 生成 [2-(N'-nitrocarbamimidoyl)hydrazinylidene]acetic acid
  参考文献：
  名称：

  1-氨基-2-硝基胍与α-酮羧酸的反应

  摘要：

  1-氨基-2-硝基胍与α-酮羧酸的反应得到α-酮羧酸的取代，其环化取决于偶氮甲碱部分的几何形状。已经确定，当其线性前体的以Z（syn）-异构体形式存在时，所获得的能够形成1,2,4-三嗪系统。因此，其偶氮甲碱部分以Z型形式存在的苯乙二醛酸经历了杂环化反应，形成了取代的3-硝基亚氨基-6-苯基-4,5-二氢-1,2,4-三嗪-5（ 2 Н） -酮，而乙醛酸和methylglyoxalic酸腙，其在存在ë-配置，未参与此反应。

  DOI：

  10.1007/s10593-020-02649-w
• 作为产物：
  描述：

  乙醛酸 、 1-氨基-3-硝基胍 以 水 为溶剂， 反应 0.5h， 以82%的产率得到(2E)-2-[[(Z)-N'-nitrocarbamimidoyl]hydrazinylidene]acetic acid
  参考文献：
  名称：

  1-氨基-2-硝基胍与α-酮羧酸的反应

  摘要：

  1-氨基-2-硝基胍与α-酮羧酸的反应得到α-酮羧酸的取代，其环化取决于偶氮甲碱部分的几何形状。已经确定，当其线性前体的以Z（syn）-异构体形式存在时，所获得的能够形成1,2,4-三嗪系统。因此，其偶氮甲碱部分以Z型形式存在的苯乙二醛酸经历了杂环化反应，形成了取代的3-硝基亚氨基-6-苯基-4,5-二氢-1,2,4-三嗪-5（ 2 Н） -酮，而乙醛酸和methylglyoxalic酸腙，其在存在ë-配置，未参与此反应。

  DOI：

  10.1007/s10593-020-02649-w

文献信息

• Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid
  作者：Valerie A. Vaillancourt、Scott D. Larsen、Steven P. Tanis、Jeffery E. Burr、Mark A. Connell、Michele M. Cudahy、Bruce R. Evans、Peter V. Fisher、Paul D. May、Martin D. Meglasson、Deborah D. Robinson、F. Craig Stevens、John A. Tucker、Thomas J. Vidmar、Jen H. Yu

  DOI：10.1021/jm000094n

  日期：2001.4.1

  3-Guanidinopropionic acid (1) has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue in animal models of non-insulin-dependent diabetes mellitus (NIDDM). However, 1 has also been shown to be a substrate for both the creatine transporter and creatine kinase, leading to marked accumulation in muscle tissue as the corresponding N-phosphate. The corresponding aminoguanidine analogue 2 was recently discovered to retain the antidiabetic activity of 1 while being markedly less susceptible to creatine-like metabolism, suggesting that it should have less potential to accumulate in muscle. Further structural modification of 2 was undertaken to investigate whether the antidiabetic potency could be augmented while maintaining resistance to creatine-like metabolism. Modifications such as a-alkylation, homologation, and bioisosteric replacement of the aminoguanidine all were detrimental to antidiabetic activity. However, the simple regioisomeric aminoguanidinoacetic acid 9 and diaminoguanidinoacetic acid-analogue 7 were found to be equipotent to 2, leading eventually to the discovery of the significantly more potent diaminoguanidinoacetic acid regioisomers 52 and 53. Further attempts to modify the more active template represented by 52 led only to reductions in; antidiabetic activity. Each of the new active analogues displayed the same resistance to creatine-like metabolism as 2. Further testing of 7, 9, and 53 in obese diabetic ob;lob mice confirmed that weight loss is induced selectively from adipose tissue, similar to the lead 1. Administration of 53 to insulin-resistant rhesus monkeys led to reductions in both fasting and post-prandial plasma glucose levels with concomitant reductions in plasma insulin levels, suggesting that the compound improved the action of endogenous insulin. Compounds 7 and 53 were selected for further preclinical development.
• 1-Amino-2-nitroguanidine in reactions with α-ketocarboxylic acids
  作者：Olga Yu. Ozerova、Tatiana P. Efimova、Tamara A. Novikova

  DOI：10.1007/s10593-020-02649-w

  日期：2020.2

  The reactions of 1-amino-2-nitroguanidine with α-ketocarboxylic acids gave substituted hydrazones of α-ketocarboxylic acids, the cyclization of which depended on the geometry of the azomethine moiety. It was established that the obtained hydrazones were able to form a 1,2,4-triazine system in the case when the hydrazone of its linear precursor existed in the form of Z(syn)-isomer. Thus, the phenylglyoxalic

  1-氨基-2-硝基胍与α-酮羧酸的反应得到α-酮羧酸的取代，其环化取决于偶氮甲碱部分的几何形状。已经确定，当其线性前体的以Z（syn）-异构体形式存在时，所获得的能够形成1,2,4-三嗪系统。因此，其偶氮甲碱部分以Z型形式存在的苯乙二醛酸经历了杂环化反应，形成了取代的3-硝基亚氨基-6-苯基-4,5-二氢-1,2,4-三嗪-5（ 2 Н） -酮，而乙醛酸和methylglyoxalic酸腙，其在存在ë-配置，未参与此反应。