3,6-Diamino-5-cyan-1H-pyrazolo<3,4-b>pyridin | 1901-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 3,6-Diamino-5-cyan-1H-pyrazolo<3,4-b>pyridin
• 英文别名: 3,6-diamino-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile；3,6-diamino-1(2)H-pyrazolo[3,4-b]pyridine-5-carbonitrile；3,6-diamino-2H-pyrazolo[3,4-b]pyridine-5-carbonitrile
• CAS: 1901-68-4
• 化学式: C₇H₆N₆
• 分子量: 174.165
• InChiKey: QQMCPWOEDXMLTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-二甲氧基四氢呋喃 、 3,6-Diamino-5-cyan-1H-pyrazolo<3,4-b>pyridin 在 溶剂黄146 作用下， 反应 1.0h， 生成 3,6-di-1H-pyrrol-1-yl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  新型吡唑并吡啶和吡啶并嘧啶衍生物的合成

  摘要：

  2-氨基-6-氯吡啶-3,5-二甲腈被用作合成新的吡唑并吡啶，吡啶并嘧啶，苯并二氮杂and和苯并噻唑嗪衍生物的中间体。J.杂环化​​学。（2011）。

  DOI：

  10.1002/jhet.547
• 作为产物：
  描述：

  2-氨基-6-氯-3,5-二氰基吡啶 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以87%的产率得到3,6-Diamino-5-cyan-1H-pyrazolo<3,4-b>pyridin
  参考文献：
  名称：

  蛋白激酶抑制剂3,6-二氨基-1 H-吡唑并[3,4- b ]吡啶衍生物的合成及生物学评价

  摘要：

  报道了许多不同取代的3,6-二氨基-1 H-吡唑并[3,4- b ]吡啶衍生物的合成和生物学评价。从抑制结果中选择与疾病相关的蛋白激酶[IC 50（μM）DYRK1A = 11；CDK5 = 0.41；GSK-3 = 1.5]我们已经观察到3,6-二氨基-4-苯基-1 H-吡唑并[3,4- b ]吡啶-5-甲腈（4）构成了潜在的新颖且简单的先导化合物用于治疗阿尔茨海默氏病的药物。

  DOI：

  10.1016/j.bmcl.2009.06.099

文献信息

• Synthesis and<i>in vitro</i>Antibacterial Activity of Some Novel Fused Pyridopyrimidine Derivatives
  作者：Mahmoud Abd El Aleem Ali Ali El-Remaily、O. M. El Hady、H. Salah Abo Zaid、E. M. M. Abd El-Raheem

  DOI：10.1002/jhet.2420

  日期：2016.7

  the reaction of compound 1 with a variety of reagents, namely, formic acid, acetic anhydride, phenyl isothiocyanate, phenyl isocyanate, carbon disulfide, acetamide and thioacetamide, which in turn were treated with hydrazine to give pyrazolopyridopyrimidine derivatives 4, 6 and 11, 12, 13. The potency of the results as antibacterial agents has been evaluated. Most of the tested products showed a highly

  吡啶并嘧啶衍生物2，5和7，8，9是由化合物的反应布置1与多种试剂，即，甲酸，乙酸酐，苯基异硫氰酸酯，苯基异氰酸酯，二硫化碳，乙酰胺和硫代乙酰胺的，而后者又是与肼，得到pyrazolopyridopyrimidine衍生物处理4，6和11，12，13。已经评估了结果作为抗菌剂的效力。大多数测试产品显示出对两种细菌菌株的高度抑制区。所有化合物均基于其IR，1 H-NMR和质谱进行了表征。
• Studies on the acetylation of 3,6-diamino-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile derivatives
  作者：Mourad Chioua、Elena Soriano、Abdelouahid Samadi、J. Marco-Contelles

  DOI：10.1002/jhet.403

  日期：——

  Abstract magnified image The acetylation reaction of the differently substituted 3,6‐diamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile derivatives 1, 2, 3, 4, 5, 6 is reported. The structure of the resulting acetamides has been investigated and confirmed by analytical, spectroscopic, and chemical transformations. From these studies, we conclude that, in general, under mild conditions, and using acetic anhydride, when free, the N(1)H moiety is a more reactive center respect to the C(3)NH2 and C(6)NH2 groups. This trend is reversed when no steric hindrance due to presence of a phenyl group at C4 drives the preferred acetylation to C(3)NH2, as it is evident by comparing the observed results from precursor 1 with 3. When N1 is blocked, the (C3)NH2 group undergoes preferential acetylation over the (C6)NH2 site, which only has been mono (or diacetylated) at reflux. Computational analyses based on DFT studies have been extensively used to explain the observed reactivities. J. Heterocyclic Chem., (2010).