2-amino-4-(3-methylphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile | 791619-78-8

• 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: 2-amino-4-(3-methylphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile
• 英文别名: 2-amino-3,5-dicarbonitrile-4-m-tolyl-6-(phenylthio)pyridine；2-amino-6-(phenylthio)-4-m-tolylpyridine-3,5-dicarbonitrile
• CAS: 791619-78-8
• 化学式: C₂₀H₁₄N₄S
• 分子量: 342.424
• InChiKey: UZDPFYGTBIRELZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 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：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3-methylphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile 在 sodium sulfide 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-Amino-6-(2-hydroxy-ethylsulfanyl)-4-m-tolyl-pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  A Series of Ligands Displaying a Remarkable Agonistic−Antagonistic Profile at the Adenosine A₁ Receptor

  摘要：

  Adenosine receptor agonists are usually variations of the natural ligand, adenosine. The ribose moiety in the ligand has previously been shown to be of great importance for the agonistic effects of the compound. In this paper, we present a series of nonadenosine ligands selective for the adenosine A(1) receptor with an extraordinary pharmacological profile. 2-Amino-4-benzo[1,3]dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile (70, LUF 5853) shows full agonistic behavior comparable with the reference compound CPA, while also displaying comparable receptor binding affinity (K-i = 11 nM). In contrast, compound 58 (2-amino-4-(3-trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5948) has a binding affinity of 14 nM and acts as an inverse agonist. Also present within this same series are compounds that show neutral antagonism of the adenosine A(1) receptor, for example compound 65 (2-amino-4-(4-difluoromethoxyphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5826).

  DOI：

  10.1021/jm049597+
• 作为产物：
  描述：

  3-甲基苯甲醛 在 哌啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-amino-4-(3-methylphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  A Series of Ligands Displaying a Remarkable Agonistic−Antagonistic Profile at the Adenosine A₁ Receptor

  摘要：

  Adenosine receptor agonists are usually variations of the natural ligand, adenosine. The ribose moiety in the ligand has previously been shown to be of great importance for the agonistic effects of the compound. In this paper, we present a series of nonadenosine ligands selective for the adenosine A(1) receptor with an extraordinary pharmacological profile. 2-Amino-4-benzo[1,3]dioxol-5-yl-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile (70, LUF 5853) shows full agonistic behavior comparable with the reference compound CPA, while also displaying comparable receptor binding affinity (K-i = 11 nM). In contrast, compound 58 (2-amino-4-(3-trifluoromethylphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5948) has a binding affinity of 14 nM and acts as an inverse agonist. Also present within this same series are compounds that show neutral antagonism of the adenosine A(1) receptor, for example compound 65 (2-amino-4-(4-difluoromethoxyphenyl)-6-(2-hydroxyethylsulfanyl)pyridine-3,5-dicarbonitrile, LUF 5826).

  DOI：

  10.1021/jm049597+

文献信息

• SnO nanoparticles as an efficient catalyst for the one-pot synthesis of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines
  作者：Javad Safaei-Ghomi、Hossein Shahbazi-Alavi、Elham Heidari-Baghbahadorani

  DOI：10.1039/c4ra04769a

  日期：——

  SnO nanoparticles have been used as an efficient catalyst for the preparation of chromeno[2,3-b]pyridines and 2-amino-3,5-dicyano-6-sulfanyl pyridines under reflux conditions in ethanol in good to excellent yields. This flexible and nano-catalytic procedure showed good recyclability and provides a clean condensation reaction in a short reaction time.

  SnO纳米颗粒已被用作高效的催化剂，用于在乙醇中回流条件下以良好至极好的收率制备苯并[2,3- b ]吡啶和2-氨基-3,5-二氰基-6-硫烷基吡啶。这种灵活的纳米催化程序显示出良好的可回收性，并在较短的反应时间内提供了干净的缩合反应。
• DBU-catalyzed three-component one-pot synthesis of highly functionalized pyridines in aqueous ethanol
  作者：Ritu Mamgain、Ram Singh、Diwan S. Rawat

  DOI：10.1002/jhet.32

  日期：2009.1

  1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) efficiently catalyzes three-component one-pot condensations of aldehyde, malononitrile, and thiophenol to produce highly functionalized pyridines in excellent yield in aqueous ethanol. J. Heterocyclic Chem., 46, 69 (2009).

  1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）有效催化醛的三组分一锅缩合，丙二腈和苯硫酚在乙醇水溶液中以优异的收率生产高度官能化的吡啶。杂环化学杂志，46，69（2009）。
• CuI nanoparticles: a highly active and easily recyclable catalyst for the synthesis of 2-amino-3,5-dicyano-6-sulfanyl pyridines
  作者：Javad Safaei-Ghomi、Mohammad Ali Ghasemzadeh

  DOI：10.1080/17415993.2012.728220

  日期：2013.6.1

  CuI nanoparticles as a worthwhile and reusable catalyst supply an eco-friendly procedure for the synthesis of 2-amino-3,5-dicyano-6-sulfanyl pyridine derivatives. The products were obtained in high yields and short reaction times via multicomponent reaction of aldehydes, malononitrile and thiols under reflux conditions. The method presented is mild, efficient, inexpensive and satisfactory to give the products in the presence of novel nanoscale materials.
• WEB (water extract of banana): An efficient natural base for one-pot multi-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines
  作者：Alireza Allahi、Batool Akhlaghinia

  DOI：10.1080/10426507.2020.1835905

  日期：2021.3.4

  One-pot multi-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines derivatives using WEB (water extract of banana peels ash) as a green catalyst is described. A variety of aromatic aldehydes (with electron-donating and electron-withdrawing groups) in conjunction with aromatic and aliphatic thiols are known to tolerate this reaction condition using WEB. The reaction has simple work up procedure without using toxic solvents.
• Safaei-Ghomi, Javad; Ghasemzadeh, Mohammad Ali, Acta Chimica Slovenica, 2012, vol. 59, # 3, p. 697 - 702
  作者：Safaei-Ghomi, Javad、Ghasemzadeh, Mohammad Ali

  DOI：——

  日期：——