4-(4-chlorophenyl)-2-oxo-6-pyridin-4-yl-1H-pyridine-3-carbonitrile

• 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: 4-(4-chlorophenyl)-2-oxo-6-pyridin-4-yl-1H-pyridine-3-carbonitrile
• 化学式: C₁₇H₁₀ClN₃O
• 分子量: 307.739
• InChiKey: BLKWMYYBXRACFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-2-oxo-6-pyridin-4-yl-1H-pyridine-3-carbonitrile 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 8.0h， 以59%的产率得到4-(4-Chloro-phenyl)-6-thioxo-1,6-dihydro-[2,4']bipyridinyl-5-carbonitrile
  参考文献：
  名称：

  Novel milrinone analogs of pyridine-3-carbonitrile derivatives as promising cardiotonic agents

  摘要：

  In an attempt to design new inotropic drugs for congestive heart failure (CHF) with less proarrhythmic potential, three series of compounds analogous to mirlinone were prepared, namely, 4-aryl-6-(4-pyridyl)-2-oxo-1,2-dihydropyridine-3-carbonitriles 2a-g, 4-aryl-6-(4-pyridyl)-2thioxo-1,2-dihydropyridine-3-carbonitriles 3a-g and 2-amino-4-aryl-6-(4-pyridyl)-pyridine-3-carbonitriles 4a-g. The first series was prepared by reacting 4-acetyl pyridine with the appropriate aldehyde, ethyl cyanoacetate and ammonium acetate in ethanol. Reaction of 2a-g with phosphorus pentasulfide afforded the second series 3a-g. The third target compounds 4a-g were prepared applying the same procedure used to synthesize 2a-g using malononitrile instead of ethyl cyanoacetate. All the newly synthesized compounds were evaluated for their cardiotonic activity and their in vivo cardiovascular effects. In addition, their oral and parentral acute toxicity were determined. Compounds 2a, 2b, 2c, 4c and 4f proved to exert cardiotonic activity comparable to that of milfinone using spontaneously beating atria model from reserpine-treated guinea pigs. In addition these compounds proved to be non-toxic and well tolerated by mice up to 250 mg kg(-1) orally and up to 125 mg kg(-1) through parenteral route. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.06.005
• 作为产物：
  描述：

  4-乙酰吡啶 、 4-氯苯甲醛 、 氰乙酸乙酯 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.42h， 以88%的产率得到4-(4-chlorophenyl)-2-oxo-6-pyridin-4-yl-1H-pyridine-3-carbonitrile
  参考文献：
  名称：

  Fe 3 O 4 @SiO 2 @（CH 2）3-脲硫脲：一种新型的氢键键合和可重复使用的催化剂，用于通过基于乙烯基异端基的协同氧化作用构建联吡啶-5-腈

  摘要：

  制备了Fe 3 O 4 @SiO 2 @（CH 2）3-脲硫脲作为新型的氢键可回收纳米磁性催化剂，并通过透射电子显微镜（TEM），热重分析/导数热重分析（TGA / DTG）证实了其结构。 ），振动样品磁力计（VSM），傅立叶变换红外（FT-IR）光谱，场发射扫描电子显微镜（FESEM），能量色散光谱（EDS）和元素图分析。新型氢键催化剂的催化性能可以通过联吡啶5-腈的多组分制备进行考察。在不存在任何溶剂的情况下，基于乙烯基异氰酸酯的协同氧化（CVABO）机理。新型氢键结合的纳米磁性催化剂可以很容易地获得并重复使用四次，而不会明显破坏催化效率。

  DOI：

  10.1016/j.mcat.2020.111201

文献信息

• Synthesis of Selective Bioactive Pyridylpyridones: in silico Studies and Biological Evaluations
  作者：Suresh Ramasamy、Singanan Ponnuchamy、Sivakumar Ponnusamy

  DOI：10.14233/ajchem.2020.22290

  日期：——

  Twenty three substituted pyridylpyridones were designed and performed for molecular docking studies against α-amylase enzyme. The top three hit molecules were synthesized and characterized by 1H NMR, 13C NMR, ESI-mass and FT-IR spectroscopic techniques. Experimental biological applications were studied for these compounds. The DFT calculations were executed for the hit compounds. In addition, molecular electrostatic potential mapping was also executed for additional support.

  设计并进行了23个取代吡啶基吡啶酮分子对α-淀粉酶酶进行分子对接研究。其中前三个命中分子被合成并通过1H NMR、13C NMR、ESI-mass和FT-IR光谱技术进行表征。这些化合物的实验生物应用也被研究。对这些命中化合物进行了DFT计算。此外，还进行了分子电荷密度图绘制以提供额外支持。
• Fe3O4@SiO2@(CH2)3-urea-thiourea: A novel hydrogen-bonding and reusable catalyst for the construction of bipyridine-5-carbonitriles via a cooperative vinylogous anomeric based oxidation
  作者：Fatemeh Karimi、Meysam Yarie、Mohammad Ali Zolfigol

  DOI：10.1016/j.mcat.2020.111201

  日期：2020.12

  elemental mapping analysis. The catalytic performance of the novel hydrogen-bonding catalyst was appropriately probed through the multicomponent preparation of bipyridine-5-carbonitriles via a cooperative vinylogous anomeric based oxidation (CVABO) mechanism in the absence of any solvent. The novel hydrogen-bonding nanomagnetic catalyst can readily be regained and reused four times without appreciable

  制备了Fe 3 O 4 @SiO 2 @（CH 2）3-脲硫脲作为新型的氢键可回收纳米磁性催化剂，并通过透射电子显微镜（TEM），热重分析/导数热重分析（TGA / DTG）证实了其结构。 ），振动样品磁力计（VSM），傅立叶变换红外（FT-IR）光谱，场发射扫描电子显微镜（FESEM），能量色散光谱（EDS）和元素图分析。新型氢键催化剂的催化性能可以通过联吡啶5-腈的多组分制备进行考察。在不存在任何溶剂的情况下，基于乙烯基异氰酸酯的协同氧化（CVABO）机理。新型氢键结合的纳米磁性催化剂可以很容易地获得并重复使用四次，而不会明显破坏催化效率。
• Novel milrinone analogs of pyridine-3-carbonitrile derivatives as promising cardiotonic agents
  作者：Adnan A. Bekhit、Azza M. Baraka

  DOI：10.1016/j.ejmech.2005.06.005

  日期：2005.12

  In an attempt to design new inotropic drugs for congestive heart failure (CHF) with less proarrhythmic potential, three series of compounds analogous to mirlinone were prepared, namely, 4-aryl-6-(4-pyridyl)-2-oxo-1,2-dihydropyridine-3-carbonitriles 2a-g, 4-aryl-6-(4-pyridyl)-2thioxo-1,2-dihydropyridine-3-carbonitriles 3a-g and 2-amino-4-aryl-6-(4-pyridyl)-pyridine-3-carbonitriles 4a-g. The first series was prepared by reacting 4-acetyl pyridine with the appropriate aldehyde, ethyl cyanoacetate and ammonium acetate in ethanol. Reaction of 2a-g with phosphorus pentasulfide afforded the second series 3a-g. The third target compounds 4a-g were prepared applying the same procedure used to synthesize 2a-g using malononitrile instead of ethyl cyanoacetate. All the newly synthesized compounds were evaluated for their cardiotonic activity and their in vivo cardiovascular effects. In addition, their oral and parentral acute toxicity were determined. Compounds 2a, 2b, 2c, 4c and 4f proved to exert cardiotonic activity comparable to that of milfinone using spontaneously beating atria model from reserpine-treated guinea pigs. In addition these compounds proved to be non-toxic and well tolerated by mice up to 250 mg kg(-1) orally and up to 125 mg kg(-1) through parenteral route. (c) 2005 Elsevier SAS. All rights reserved.