3-amino-4H-[1,2,4]triazin-5-one | 1121-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-amino-4H-[1,2,4]triazin-5-one
• 英文别名: 3-Amino-2,5-dihydro-1,2,4-triazin-5-one；3-amino-4H-1,2,4-triazin-5-one
• CAS: 1121-90-0
• 化学式: C₃H₄N₄O
• mdl: MFCD00707810
• 分子量: 112.091
• InChiKey: OWAYVVLCHUWASK-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  235.2±23.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4H-[1,2,4]triazin-5-one 在 六甲基磷酰三胺 、 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 反应 4.0h， 以69%的产率得到3-amino-as-triazine-5-thione
  参考文献：
  名称：

  Hwang, Long-Chih; Wei, Dau-Chang; Han, Chein-Hwa, Journal of Chemical Research, Miniprint, 1994, # 4, p. 831 - 842

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-1,2,4-triazin-3-imine 在 双氧水 、 溶剂黄146 作用下， 生成 3-amino-4H-[1,2,4]triazin-5-one
  参考文献：
  名称：

  Jovanovic, Misa V., Heterocycles, 1986, vol. 24, # 4, p. 951 - 966

  摘要：

  DOI：

文献信息

• Highly Diastereoselective Synthesis of C(6)-Functionalized Dihydroimidazotriazines
  作者：Ethel Garnier、Jérôme Guillard、Eric Pasquinet、Franck Suzenet、Didier Poullain、Christian Jarry、Jean-Michel Léger、Bruno Lebret、Gérald Guillaumet

  DOI：10.1021/ol035743e

  日期：2003.11.1

  [reaction: see text] The first examples of C(6)-substituted 7-hydroxy-6,7-dihydro-5H-imidazo[1,2-b][1,2,4]triazines have been prepared by ring closure of different 5(2H)-1,2,4-triazin-3-ones 1a-c with 40% aqueous glyoxal and various nucleophiles (alcohols, thiols, or amines). The structure and exact stereochemistry of 2a was established by a single X-ray diffraction study and (1)H and (13)C NMR spectra

  [反应：见正文]通过闭环制备了C（6）-取代的7-羟基-6,7-二氢-5H-咪唑并[1,2-b] [1,2,4]三嗪的第一个实例40％乙二醛水溶液和各种亲核试剂（醇，硫醇或胺）的不同5（2H）-1,2,4-三嗪-3-酮1a-c的组成。通过一次X射线衍射研究以及（1）H和（13）C NMR光谱分析，确定了2a的结构和确切的立体化学。结果表明，该过程是完全区域选择性和非对映选择性的。提出了一种涉及亚胺中间体的机理。
• 6-Aza-2‘-deoxyisocytidine:  Synthesis, Properties of Oligonucleotides, and Base-Pair Stability Adjustment of DNA with Parallel Strand Orientation
  作者：Frank Seela、Yang He

  DOI：10.1021/jo020507n

  日期：2003.1.1

  into phosphoramidite building blocks, and incorporated into oligodeoxynucleotides. The glycosylic bond stability of 1a,b under acidic conditions increases compared to that of 5-methyl-2'-deoxyisocytidine (2a) and 2'-deoxyisocytidine (2b). Oligonucleotides incorporating 1a or 1b show an enhanced stability against the 3'-exonuclease snake-venom phosphodiesterase. The duplexes containing 6-azapyrimidine nucleosides

  已合成6-Aza-5-甲基-2'-脱氧异胞苷（1a）和6-Aza-2'-脱氧异胞苷（1b），将其转化为亚磷酰胺结构单元，并掺入寡脱氧核苷酸中。与5-甲基-2'-脱氧异胞苷（2a）和2'-脱氧异胞苷（2b）相比，酸性条件下1a，b的糖基键稳定性增加。掺入1a或1b的寡核苷酸显示出对3'-核酸外切酶蛇毒磷酸二酯酶的增强的稳定性。含有6-氮杂嘧啶核苷1a或1b的双链体的T（m）值比含有2a或2b的具有反平行或平行链取向的双链体的T（m）值低。这用于将三齿m5iCd-dG碱基对的稳定性调节为反向二齿Watson-Crick dA-dT对的水平。
• 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.
• SYNTHESIS OF SOME NEW PROPANOL DERIVATIVES ANALOGOUS TO FLUCONAZOLE
  作者：Majid M. Heravi、Radineh Motamedi

  DOI：10.1080/10426500490485066

  日期：2004.11.1

  A series of 2-(2,4-difluorophenyl,)-1-(1H-1,2,4 triazol-1-yl-methyl)-3-(substituted heterocycl)-propan-2-ol, which are analogous to fluconazole, were synthesized via the reaction of 2-(2,4-difluorophenyl)-2-[1(1,2,4-triazolmethide)]oxiran with various heterocyclic systems.
• RAPID SYNTHESIS OF SOME NEW PROPANOL DERIVATIVES ANALOGOUS TO FLUCONAZOLE UNDER MICROWAVE IRRADIATION IN SOLVENTLESS SYSTEM
  作者：Majid M. Heravi、Radineh Motamedi

  DOI：10.1515/hc.2005.11.1.19

  日期：2005.1

表征谱图