1-(6-amino-5-cyano-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-phenylthiourea | 960001-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(6-amino-5-cyano-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-phenylthiourea
• 英文别名: 1-(6-amino-5-cyano-4-pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-phenylthiourea
• CAS: 960001-82-5
• 化学式: C₁₉H₁₄N₈S
• 分子量: 386.44
• InChiKey: GLJCNOIAIRTOJN-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C(Solvent: Ethanol)
• 沸点：
  734.4±70.0 °C(predicted)
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(6-amino-5-cyano-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-phenylthiourea 、 2-氯乙酰乙酸乙酯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以69%的产率得到3-[(5-acetyl-hydroxy-3-phenyl-1,3-thiazol-2(3H)-ylidene)amino]-6-amino-4-pyridin-3-yl-1H-pyrazolo[3,4-b]pyridin-5-carbonitrile
  参考文献：
  名称：

  Synthesis, Characterization, and Antiviral Activities of Pyridopyrazolotriazines

  摘要：

  A pyrazolo[3,4-b]pyridine-5-carbonitrile derivative was diazotized to give the corresponding diazonium salt, which was used as a good synthon to synthesize pyrido[2',3':3,4]pyrazolo[5,1-c]triazines via its coupling with several active hydrogen-containing reagents, e.g., 2,4-pentandione, ethyl 3-oxo-butanoate, diethylmalonate, malononitrile, 2-cyanoethanethioamide, and ethyl cyanoacetate. Also, it reacted with phenylisothiocyanate to afford the corresponding pyrazolo[3,4-b]pyridin-3-ylphenylthiourea derivative, which, in turn, was used for further chemical transformations. The data of IR, H-1 NMR, mass spectra, and chemical analyses elucidated the structures of all newly synthesized heterocyclic compounds. Cytotoxicity, anti-HSV1 and anti-HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.

  DOI：

  10.1080/10426500600887313
• 作为产物：
  描述：

  3,6-diamino-4-pyridin-3-yl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile 、 硫代异氰酸苯酯 在 吡啶 、 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以77%的产率得到1-(6-amino-5-cyano-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-3-phenylthiourea
  参考文献：
  名称：

  Synthesis, Characterization, and Antiviral Activities of Pyridopyrazolotriazines

  摘要：

  A pyrazolo[3,4-b]pyridine-5-carbonitrile derivative was diazotized to give the corresponding diazonium salt, which was used as a good synthon to synthesize pyrido[2',3':3,4]pyrazolo[5,1-c]triazines via its coupling with several active hydrogen-containing reagents, e.g., 2,4-pentandione, ethyl 3-oxo-butanoate, diethylmalonate, malononitrile, 2-cyanoethanethioamide, and ethyl cyanoacetate. Also, it reacted with phenylisothiocyanate to afford the corresponding pyrazolo[3,4-b]pyridin-3-ylphenylthiourea derivative, which, in turn, was used for further chemical transformations. The data of IR, H-1 NMR, mass spectra, and chemical analyses elucidated the structures of all newly synthesized heterocyclic compounds. Cytotoxicity, anti-HSV1 and anti-HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.

  DOI：

  10.1080/10426500600887313

文献信息

• Synthesis, Characterization, and Antiviral Activities of Pyridopyrazolotriazines
  作者：Fawzy A. Attaby、A. H. Elghandour、M. A. Ali、Yasser M. Ibrahem

  DOI：10.1080/10426500600887313

  日期：2007.1.1

  A pyrazolo[3,4-b]pyridine-5-carbonitrile derivative was diazotized to give the corresponding diazonium salt, which was used as a good synthon to synthesize pyrido[2',3':3,4]pyrazolo[5,1-c]triazines via its coupling with several active hydrogen-containing reagents, e.g., 2,4-pentandione, ethyl 3-oxo-butanoate, diethylmalonate, malononitrile, 2-cyanoethanethioamide, and ethyl cyanoacetate. Also, it reacted with phenylisothiocyanate to afford the corresponding pyrazolo[3,4-b]pyridin-3-ylphenylthiourea derivative, which, in turn, was used for further chemical transformations. The data of IR, H-1 NMR, mass spectra, and chemical analyses elucidated the structures of all newly synthesized heterocyclic compounds. Cytotoxicity, anti-HSV1 and anti-HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.