6-amino-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile | 126774-73-0

• 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: 6-amino-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
• 英文别名: 6-amino-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-carbonitrile；6-amino-4-(4-chlorophenyl)-3-methyl-2H-pyrazolo[3,4-b]pyridine-5-carbonitrile
• CAS: 126774-73-0
• 化学式: C₁₄H₁₀ClN₅
• 分子量: 283.72
• InChiKey: NBLJSHVOFCYBPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 以 乙醇 为溶剂， 生成 6-amino-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Convenient Ultrasound-Promoted Regioselective Synthesis of Fused 6-Amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

  摘要：

  [image omitted] A multicomponent, catalyst-free reaction for the synthesis of fused 6-amino-3-methyl-4-aryl-1H-pyrazolo [3,4-b] pyridine-5-carbonitrile from 3-amino-5-methylpyrazole, malononitrile, and substituted aldehydes under ultrasound irradiation in short reaction times (8-10min) with good yields (85-98%) is reported.

  DOI：

  10.1080/00397911.2010.502990

文献信息

• Catalyst-free grinding method: a new avenue for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and DFT studies on the mechanistic pathway of this category of compounds
  作者：Mohammad Nikpassand、Leila Zare Fekri、Parissa Naddaf Rahro

  DOI：10.1007/s11164-018-3701-9

  日期：2019.4

  A novel, efficient, one-pot, catalyst-free grinding procedure for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile is reported. The condensation of substituted benzaldehydes, 3-amino-5-methylpyrazole, and malononitrile according to a three-component reaction was investigated using density functional theory (DFT) at B3LYP/6-311G level to explore the reaction mechanism.

  报道了一种新颖，高效，一锅无催化剂的研磨程序，用于合成6-氨基-3-甲基-4-芳基-1 H-吡唑并[3,4- b ]吡啶-5-甲腈。利用密度泛函理论（DFT）在B3LYP / 6-311G水平上研究了取代的苯甲醛，3-氨基-5-甲基吡唑和丙二腈根据三组分反应的缩合反应，探讨了其反应机理。研究了所有路线，优化了中间体的结构，并找到了所有的过渡态。计算结果表明，所提出的机制依赖于四个中间体。
• Synthesis and antitumor evaluation of some new thiazolopyridine, nicotinonitrile, pyrazolopyridine, and polyhydroquinoline derivatives using ceric ammonium nitrate as a green catalyst
  作者：Reham R. Raslan、Sadia A. Hessein、Sawsan A. Fouad、Nadia A. M. Shmiess

  DOI：10.1002/jhet.4423

  日期：2022.5

  A novel series of thiazolo[5,4-b]pyridine, polysubstituted pyridines, pyrazolo [3,4-b] pyridine-5-carbonitriles, and polyhydroquinoline were synthesized via one-pot reaction of 2-iminothiazolidin-5-one, acetyl pyridine, pyrazolone, and/or cyclohexanone with various aldehydes, some active methylene and ammonium acetate in the presence of ceric ammonium nitrate (CAN). The resulting compounds were generated

  通过 2-亚氨基噻唑烷-5-酮、乙酰基的一锅反应合成了一系列新型噻唑并[5,4 - b ]吡啶、多取代吡啶、吡唑并[3,4- b ]吡啶-5-甲腈和聚氢喹啉在硝酸铈铵 (CAN) 存在下，吡啶、吡唑啉酮和/或环己酮与各种醛、一些活性亚甲基和乙酸铵。所得化合物在短时间内以高产率生成，并使用 IR、1 H NMR、13 C-NMR 和质谱确认了新化合物的结构。体外测试了 15 种物质对 HePG-2 和 Caco-2 细胞系的细胞毒活性。抗肿瘤试验结果证实喹啉12d化合物对两种接近于多柔比星的细胞系具有更高的细胞毒活性，多柔比星被用作标准抗癌药物。此外，12c化合物对 2 细胞系具有更有效的抗肿瘤作用。而化合物1对 Caco-2 表现出中等活性。另一方面，大多数测试化合物对这两种细胞系表现出中度至低度的细胞毒活性。根据结果​​，一些新合成的衍生物显示出优异的抗肿瘤活性，使其可用于生物医学应用。
• Aluminum hydrogen sulfate as a green catalyst for the solvent-free synthesis of pyrazolopyridines
  作者：M. Nikpassand、L. Zare Fekri

  DOI：10.1134/s1070363215050308

  日期：2015.5

  Aluminum hydrogen sulfate turned out to be a mild, convenient, and efficient reagent for the conversion of substituted benzyl alcohols into pyrazolopyridines via condensation with 3-methyl-1H-pyrazole-5-amine and CH acid (malononitrile or indan-1,3-dione) at room temperature under solvent-free conditions with high yield, high purity, and short reaction time.