3,6,7,8-tetrahydrocyclopenta[d]pyrazolo[3,4-b]pyridin-1-amine | 1547812-00-9

• 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: 3,6,7,8-tetrahydrocyclopenta[d]pyrazolo[3,4-b]pyridin-1-amine
• 英文别名: 4,5,7-Triazatricyclo[7.3.0.02,6]dodeca-1(9),2,5,7-tetraen-3-amine
• CAS: 1547812-00-9
• 化学式: C₉H₁₀N₄
• 分子量: 174.205
• InChiKey: MUBICTLYQXUKAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-chloro-6,7-dihydro-5H-cyclopenta[c]pyridine-4-carbonitrile 在 hydrazine hydrate 作用下， 反应 2.0h， 以99%的产率得到3,6,7,8-tetrahydrocyclopenta[d]pyrazolo[3,4-b]pyridin-1-amine
  参考文献：
  名称：

  Synthesis and bioactivity of novel amino-pyrazolopyridines

  摘要：

  Here we describe the synthesis and biological activity of novel amino-pyrazolopyridines with anti-NF-kappa B and pro-apoptotic potential. alpha-Methylene ketones were used as a starting point for synthesis of amino-pyrazolopyridine 3. The alkylidene malononitriles 1 were obtained by the Knoevenagel reaction of ketones with malononitriles. Vilsmeier-Haack reaction allowed direct access to 2-chloro-3-cyanopyridines 2. Those products, by refluxing with hydrazine hydrate, allowed cyclization to amino-pyrazolopyridines 3a-g, which were not previously described in the literature.Bioactivity results indicated that amino-pyrazolopyridines 3a, 3b and 3g induced apoptotic cell death in K562 cancer cells with an IC50 of 36.5 +/- 3.9 mu M, 27.6 +/- 4.5 mu M and 35.0 +/- 2.3 mu M, respectively, after 72 h. In addition, compounds 3a, 3b and 3g exerted NF-kappa B inhibition activity with an IC50 of 4.7 +/- 1.6 mu M, 6.9 +/- 1.9 mu M and 39.8 +/- 3.9 mu M, respectively, after 8 h in K562 cells activated with TNF alpha. Compounds 3b and 3g showed interesting differential toxicity as viability of peripheral blood mononuclear cells (PBMCs) from healthy donors remained largely unaffected by this treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.008