4-(1-methyl-1H-pyrrol-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-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-(1-methyl-1H-pyrrol-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 4-(1-methylpyrrol-2-yl)-2-oxo-6-phenyl-1H-pyridine-3-carbonitrile
• 化学式: C₁₇H₁₃N₃O
• 分子量: 275.31
• InChiKey: PVDBMSLQOOZNIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(1-methyl-1H-pyrrol-2-yl)-1-phenylprop-2-yn-1-one 、 氰乙酰胺 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.5h， 以98%的产率得到4-(1-methyl-1H-pyrrol-2-yl)-2-oxo-6-phenyl-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  Bio-inspired Functionalized Pyrrole-Pyridone Ensembles: Synthesis on the Platform of Acylethynylpyrroles

  摘要：

  通过将可获得的酰乙炔基吡咯烷与亚甲基活性酰胺反应，可以高效合成具有药理学导向的官能化吡咯-吡啶酮合集，几乎可以实现定量收率。这种环缩合在室温下在KOH/DMSO超碱悬浮液中顺利进行。

  DOI：

  10.1055/s-0040-1707148

文献信息

• Microwave-assisted synthesis of certain pyrrolylpyridines, some derived ring systems and their evaluation as anticancer and antioxidant agents
  作者：Sherif A.F. Rostom、Adnan A. Bekhit

  DOI：10.1016/j.ejmech.2015.01.023

  日期：2015.3

  The synthesis of 18 novel pyrrolylpyridines and some derived bi-, tri- and tetracyclic ring systems using both the conventional heating and MW irradiation techniques is described. Fourteen compounds; 2-9, 10-12, 14, 17 and 18 were evaluated for their antitumor activity according to the National Cancer Institute (NCI), in vitro disease oriented antitumor screening. Distinctive antitumor activity was conjugated with compounds 3 and 7 (R = 3,4-di-OCH3-C6H3). The analogs 3, 6, 7, 9, 10, 11 and 12 which exhibited prominent antitumor activity, were further evaluated for their antioxidant potential using the DPPH radical scavenging assay. The substituted 6-(3,4-dimethoxyphenyl)pyridine-3-carbonitriles 3 and 7 were nearly equipotent to BHT the standard antioxidant utilized in this assay (scavenging activity 31 and 33%, respectively, vs 36%). Accordingly, compounds 3 and 7 can be considered as lead structures for dual antitumor and antioxidant activities. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Bio-inspired Functionalized Pyrrole-Pyridone Ensembles: Synthesis on the Platform of Acylethynylpyrroles
  作者：Boris A. Trofimov、Ivan V. Saliy、Maxim D. Gotsko、Lyubov N. Sobenina、Igor A. Ushakov

  DOI：10.1055/s-0040-1707148

  日期：2020.9

  An efficient synthesis of pharmacologically oriented, functionalized pyrrole-pyridone ensembles by the reaction of available acylethynylpyrroles with methylene active amides in almost quantitative yields has been implemented. The cyclocondensation proceeds smoothly at room temperature in a KOH/DMSO superbase suspension.

  通过将可获得的酰乙炔基吡咯烷与亚甲基活性酰胺反应，可以高效合成具有药理学导向的官能化吡咯-吡啶酮合集，几乎可以实现定量收率。这种环缩合在室温下在KOH/DMSO超碱悬浮液中顺利进行。