4,6-diphenyl-2-methylthiopyridine-3-carbonitrile | 90732-63-1

• 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: 4,6-diphenyl-2-methylthiopyridine-3-carbonitrile
• 英文别名: 2-(methylthio)-4,6-diphenylnicotinonitrile；3-Pyridinecarbonitrile, 2-(methylthio)-4,6-diphenyl-；2-methylsulfanyl-4,6-diphenylpyridine-3-carbonitrile
• CAS: 90732-63-1
• 化学式: C₁₉H₁₄N₂S
• 分子量: 302.4
• InChiKey: SVLOICMGJVRFED-UHFFFAOYSA-N

物化性质

• 沸点：
  488.6±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-diphenyl-2-methylthiopyridine-3-carbonitrile 在 potassium permanganate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以85%的产率得到4,6-diphenyl-2-methylsulphonylpyridine-3-carbonitrile
  参考文献：
  名称：

  Victory, Pedro; Borrell, Jose I.; Cirujeda, Joan, Heterocycles, 1993, vol. 36, # 4, p. 777 - 783

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methylthio-3-cyano-4,6-diphenyl-1,4-dihydropyridine 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 4,6-diphenyl-2-methylthiopyridine-3-carbonitrile
  参考文献：
  名称：

  Method for the production of 2-alkylthio-3-cyano-1,4-dihydropyridines

  摘要：

  DOI：

  10.1007/bf00513589

文献信息

• Reductive desulfurization of 3-cyano-2-methylthiopyridines under the action of Raney nickel
  作者：A. A. Zubarev、V. K. Zav’yalova、V. P. Litvinov

  DOI：10.1007/s11172-006-0158-6

  日期：2005.11

  The action of Raney nickel on substituted 3-cyano-2-methylthiopyridines was studied. Under conditions of catalytic hydrogenation, the reaction yields a mixture containing the aminosulfide resulting from reduction of the nitrile group with retention of the methylthio group, the nitrile resulting from elimination of the methylthio group, and the amine resulting from both reduction of the nitrile group

  研究了雷尼镍对取代的 3-氰基-2-甲基硫代吡啶的作用。在催化加氢条件下，反应生成的混合物含有由腈基还原而保留甲硫基的氨基硫化物、由甲硫基消除的腈和由腈基和甲硫基同时还原产生的胺。消除甲硫基。在脱硫条件下用大量阮内镍处理 3-氰基-2-甲硫基吡啶可同时消除甲硫基和将腈基还原为氨基甲基。在甲醇或四氢呋喃中还原脱硫生成伯胺，而在异丙醇或乙醇中反应生成仲胺或叔胺，
• 3-(2-methylthiopyridin-3-yl)-3-oxopropionic esters
  作者：A. A. Zubarev、V. K. Zav’yalova、A. M. Shestopalov

  DOI：10.1007/s11172-011-0082-2

  日期：2011.3

  A reaction of alkyl bromoacetates with substituted 3-cyano-2-methylthiopyridines in the presence of zinc dust furnishes 3-amino-3-(2-methylthiopyridin-3-yl)propenoic esters. Their hydrolysis under mild conditions leads to 3-(2-methylthiopyridin-3-yl)-3-oxopropionic esters. The latter were used in the synthesis of pyridine-substituted pyrazolones.

  溴乙酸烷基酯与取代的 3-氰基-2-甲硫基吡啶在锌粉存在下发生反应，生成 3-氨基-3-（2-甲硫基吡啶-3-基）丙烯酸酯。在温和的条件下进行水解，可得到 3-(2-甲硫基吡啶-3-基)-3-氧代丙酸酯。后者被用于合成吡啶取代的吡唑酮。
• ——
  作者：A. A. Zubarev、V. K. Zavyalova、V. P. Litvinov

  DOI：10.1023/a:1024472914598

  日期：——

  The reactions of substituted 3-cyanopyridine-2(1H)-thiones and 3-cyano-2-(methylthio)pyridines with lithium aluminum hydride in anhydrous diethyl ether afforded the corresponding 3-aminomethyl derivatives, which were used in the synthesis of the corresponding amides.
• 4,6-Diphenylpyridines as Promising Novel Anti-Influenza Agents Targeting the PA–PB1 Protein–Protein Interaction: Structure–Activity Relationships Exploration with the Aid of Molecular Modeling
  作者：Iuni M. L. Trist、Giulio Nannetti、Cristina Tintori、Anna Lucia Fallacara、Davide Deodato、Beatrice Mercorelli、Giorgio Palù、Maikel Wijtmans、Tzveta Gospodova、Ewald Edink、Mark Verheij、Iwan de Esch、Lilia Viteva、Arianna Loregian、Maurizio Botta

  DOI：10.1021/acs.jmedchem.5b01935

  日期：2016.3.24

  Influenza is an infectious disease that represents an important public health burden, with high impact on the global morbidity, mortality, and economy. The poor protection and the need of annual updating of the anti-influenza vaccine, added to the rapid emergence of viral strains resistant to current therapy make the need for antiviral drugs with novel mechanisms of action compelling. In this regard, the viral RNA polymerase is an attractive target that allows the design of selective compounds with reduced risk of resistance. In previous studies we showed that the inhibition of the polymerase acidic protein-basic protein 1 (PA-PB1) interaction is a promising strategy for the development of anti-influenza agents. Starting from the previously identified 3-cyano-4,6-diphenyl-pyridines, we chemically modified this scaffold and explored its structure activity relationships. Noncytotoxic compounds with both the ability of disrupting the PA-PB1 interaction and antiviral activity were identified, and their mechanism of target binding was clarified with molecular modeling simulations.
• KRAUZE, A. A.;PELCHER, YU. EH.;KALME, Z. A.;DUBUR, G. YA., XIMIYA GETEROTSIKL. SOEDIN., 1984, N 8, 1140-1141
  作者：KRAUZE, A. A.、PELCHER, YU. EH.、KALME, Z. A.、DUBUR, G. YA.

  DOI：——

  日期：——