6-amino-4-(4-chlorophenyl)-2-(pyridin-2-yl)pyridine-5-carbonitrile | 573706-45-3

• 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)-2-(pyridin-2-yl)pyridine-5-carbonitrile
• 英文别名: 6-amino-4-(4-chlorophenyl)-[2,2'-bipyridine]-5-carbonitrile；2-Amino-4-(4-chlorophenyl)-6-pyridin-2-ylpyridine-3-carbonitrile
• CAS: 573706-45-3
• 化学式: C₁₇H₁₁ClN₄
• 分子量: 306.754
• InChiKey: IJUZTYZKJPFWOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-4-(4-chlorophenyl)-2-(pyridin-2-yl)pyridine-5-carbonitrile 在 氢氧化钾 、 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 7-(4-chlorobenzylidene)-4-(4-chlorophenyl)-2-(pyridin-2-yl)-5-thioxo-pyrido[2',3':4,5]pyrimido[2,1-b][1,3]thiazol-8-one
  参考文献：
  名称：

  Preparation of Some Fused Pyridopyrimidine and Pyridothienotriazine Derivatives for Biological Evaluation

  摘要：

  Compounds 2 and 9 were formed using 3-(4-chloro-phenyl)-1-pyridin-2-yl propenone (1) and malononitrile or ethyl cyanoacetate, respectively. The pyridine derivative 2 was in turn used as a precursor for the preparation of some pyridopyrimidine and fused pyridopyrimidine derivatives 3-8. On the other hand, the pyridine derivative 9 was used for the preparation of thienopyridine derivatives 11 and 12. Nitrozation of compound 12 afforded pyridothienotriazine derivative 13. Some of the prepared products showed potent antimicrobial activity.

  DOI：

  10.1080/104265090968118
• 作为产物：
  描述：

  3-(4-氯苯基)-1-(吡啶-2-基)丙-2-烯-1-酮 、 丙二腈 在 乙酸铵 、 溶剂黄146 作用下， 反应 6.0h， 以85%的产率得到6-amino-4-(4-chlorophenyl)-2-(pyridin-2-yl)pyridine-5-carbonitrile
  参考文献：
  名称：

  Preparation of Some Fused Pyridopyrimidine and Pyridothienotriazine Derivatives for Biological Evaluation

  摘要：

  Compounds 2 and 9 were formed using 3-(4-chloro-phenyl)-1-pyridin-2-yl propenone (1) and malononitrile or ethyl cyanoacetate, respectively. The pyridine derivative 2 was in turn used as a precursor for the preparation of some pyridopyrimidine and fused pyridopyrimidine derivatives 3-8. On the other hand, the pyridine derivative 9 was used for the preparation of thienopyridine derivatives 11 and 12. Nitrozation of compound 12 afforded pyridothienotriazine derivative 13. Some of the prepared products showed potent antimicrobial activity.

  DOI：

  10.1080/104265090968118

文献信息

• 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。
• Preparation of Some Fused Pyridopyrimidine and Pyridothienotriazine Derivatives for Biological Evaluation
  作者：A. E. Rashad、H. H. Sayed、A. H. Shamroukh、H. M. Awad

  DOI：10.1080/104265090968118

  日期：2005.12

  Compounds 2 and 9 were formed using 3-(4-chloro-phenyl)-1-pyridin-2-yl propenone (1) and malononitrile or ethyl cyanoacetate, respectively. The pyridine derivative 2 was in turn used as a precursor for the preparation of some pyridopyrimidine and fused pyridopyrimidine derivatives 3-8. On the other hand, the pyridine derivative 9 was used for the preparation of thienopyridine derivatives 11 and 12. Nitrozation of compound 12 afforded pyridothienotriazine derivative 13. Some of the prepared products showed potent antimicrobial activity.