2-amino-4-(4-(dimethylamino)phenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile | 791619-84-6

• 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-(4-(dimethylamino)phenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile
• 英文别名: 2-amino-4-(4-dimethylamino-phenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile；2-amino-4-(4-(dimethylamino)phenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile；2-amino-4-[4-(dimethylamino)phenyl]-6-phenylsulfanylpyridine-3,5-dicarbonitrile
• CAS: 791619-84-6
• 化学式: C₂₁H₁₇N₅S
• 分子量: 371.465
• InChiKey: GHIQLFXARMPGKE-UHFFFAOYSA-N

物化性质

• 沸点：
  629.1±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4-(dimethylamino)phenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile 在 sodium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-amino-4-(4-(dimethylamino)phenyl)-6-mercaptopyridine-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：

  对二甲氨基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-amino-4-(4-(dimethylamino)phenyl)-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

• Application of novel and reusable Fe₃O₄@Co^II(macrocyclic Schiff base ligand) for multicomponent reactions of highly substituted thiopyridine and 4<i>H</i>‐chromene derivatives
  作者：Hakimeh Ebrahimiasl、Davood Azarifar、Jamshid Rakhtshah、Hassan Keypour、Masoumeh Mahmoudabadi

  DOI：10.1002/aoc.5769

  日期：2020.9

  elemental analysis (CHNS). Then, the catalytic performance was successfully investigated in the multicomponent synthesis of 2‐amino‐4‐aryl‐6‐(phenylsulfanyl)pyridine‐3,5‐dicarbonitrile and 2‐amino‐5,10‐dioxo‐4‐aryl‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carbonitrile derivatives. Furthermore, the catalyst was isolated using a simple filtration, and recovery of the nanocatalyst was demonstrated five times without

  在本研究中，我们设计并合成了固定在Fe 3 O 4上的Co II（含有1,4-二氮杂pan的大环席夫碱配体）纳米颗粒作为新型，可回收和非均相的催化剂。使用傅立叶变换红外光谱，扫描电子显微镜，透射电子显微镜，X射线衍射，能量色散X射线光谱，热重分析，振动样品磁力分析，差分反射光谱，Brunauere-Emmette等多种技术对纳米材料进行了全面表征–Teller方法，电感耦合等离子体和元素分析（CHNS）。然后，在2-氨基-4-芳基-6（苯硫基）吡啶-3,5-二腈和2-氨基-5,10-二氧代-4-芳基-5的多组分合成中成功地研究了催化性能。 10-二氢-4 H-苯并[ g] chromene-3-腈衍生物。此外，使用简单的过滤分离了催化剂，并且证实了纳米催化剂的回收五次而没有任何活性损失。
• A convenient Baker yeast accelerated, one-pot synthesis of pentasubstituted thiopyridines
  作者：Anusaya S. Chavan、Arun S. Kharat、Manisha R. Bhosle、Ramrao A. Mane

  DOI：10.1080/00397911.2017.1350982

  日期：2017.10.2

  ABSTRACT Here we report a novel Baker yeast catalyzed one pot cyclocondensation, performed at room temperature in ethanol for obtaining high yields of polyfunctionalized pyridines, 2-amino-4-aryl-3,5-dicyano-6-phenylthiopyridines. The developed protocol obeys certain green principles and is scalable and cost effective. GRAPHICAL ABSTRACT

  摘要 在这里，我们报告了一种新型贝克酵母催化的单锅环缩合反应，在室温下在乙醇中进行，以获得高产率的多官能化吡啶，2-氨基-4-芳基-3,5-二氰基-6-苯基硫代吡啶。开发的协议遵循某些绿色原则，并且具有可扩展性和成本效益。图形概要
• Tannic Acid-Cu-modified Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2@TA-Cu NPs): New recyclable magnetic catalyst for the three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines
  作者：Azam Karimian、Mahdieh Namvar–Mahboub、Fatemeh Binabaji、Sadegh Rajabi

  DOI：10.1007/s13738-022-02608-6

  日期：2022.11

  preparing high-activity magnetic Fe3O4@SiO2@Tannic Acid-Cu (Fe3O4@SiO2@TA-Cu) nanocomposite was described. Tannic acid-Cu complexes were uniformly protected on the surface of Fe3O4@SiO2 nanoparticles. The newly prepared catalyst was characterized by XRD, FT-IR, SEM, and EDX. The obtained nanocomposites showed excellent catalytic performance and good stability for the one-pot synthesis of 2-amino-3,5-dic

  描述了一种用于制备高活性磁性 Fe 3 O 4 @SiO 2 @Tannic Acid-Cu (Fe 3 O 4 @SiO 2 @TA-Cu) 纳米复合材料的有效封装-功能化程序。Fe 3 O 4 @SiO 2表面均匀保护单宁酸-Cu络合物纳米粒子。采用XRD、FT-IR、SEM和EDX对新制备的催化剂进行了表征。所获得的纳米复合材料表现出优异的催化性能和良好的稳定性，可通过醛、丙二腈和苯硫酚在水中三组分缩合一锅法合成 2-氨基-3,5-二甲腈-6-硫代吡啶。催化剂通过磁铁分离并重复使用至少五次，性能没有明显下降。使用该协议通过简单的后处理程序以高产率制备所需的产品。
• A Series of Ligands Displaying a Remarkable Agonistic−Antagonistic Profile at the Adenosine A₁ Receptor
  作者：Lisa C. W. Chang、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Ronald F. Spanjersberg、Sophie F. Roerink、Gijs van den Hout、Margot W. Beukers、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm049597+

  日期：2005.3.1

  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).