2-amino-4-(3,4-dimethoxyphenyl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile | 791619-83-5

• 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-(3,4-dimethoxyphenyl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile
• 英文别名: 2-amino-4-(3,4-dimethoxyphenyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile；2-amino-4-(3,4-dimethylxyphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile；2-amino-4-(3,4-dimethoxyphenyl)-6-phenylsulfanylpyridine-3,5-dicarbonitrile；2-amino-4-(3,4-dimethoxyphenyl)-6-(phenylthio)pyridine-3,5-dicarbonitrile
• CAS: 791619-83-5
• 化学式: C₂₁H₁₆N₄O₂S
• 分子量: 388.45
• InChiKey: NNDWWPXWMCZOEE-UHFFFAOYSA-N

物化性质

• 熔点：
  263-264 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  620.5±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-4-(3,4-dimethoxyphenyl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile 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-4-(3,4-dimethoxy-phenyl)-6-(2-hydroxy-ethylsulfanyl)-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：

  3,4-二甲氧基苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-amino-4-(3,4-dimethoxyphenyl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile
  参考文献：
  名称：

  合成，体外和计算机筛选2-氨基-4-芳基-6-（苯硫基）吡啶-3,5-二腈作为新型α-葡萄糖苷酶抑制剂。

  摘要：

  抑制α-葡萄糖苷酶对于治疗糖尿病（DM）至关重要。除许多有机支架外，以前已报道吡啶基化合物具有广泛的生物活性。本研究报告了一系列基于吡啶的合成类似物，通过体外，动力学和计算机模拟研究评估了其对α-葡萄糖苷酶抑制的潜力。为此目的，合成了2-氨基-4-芳基-6-（苯硫基）吡啶-3，5-二腈1-28，并进行了体外筛选。与标准阿卡波糖（IC50 = 750±10 µM）相比，包括1-3、7、9、11-14和16在内的几种类似物显示出许多潜在的抑制作用增加。有趣的是，化合物7（IC50 = 55.6±0.3 µM）的抑制强度是标准阿卡波糖的13倍。对最有效分子7的动力学研究揭示了竞争型抑制机制。在计算机上进行了研究以检查配体（化合物7）与α-葡糖苷酶的活性位点残基的结合模式。

  DOI：

  10.1016/j.bioorg.2020.103879

文献信息

• Heterogeneous Cu(<scp>ii</scp>)/<scp>l</scp>-His@Fe₃O₄ nanocatalyst: a novel, efficient and magnetically-recoverable catalyst for organic transformations in green solvents
  作者：Masoomeh Norouzi、Arash Ghorbani-Choghamarani、Mohsen Nikoorazm

  DOI：10.1039/c6ra19776k

  日期：——

  A novel, efficient and green Cu(II)/L-His@Fe3O4 catalyst has been applied successfully in the synthesis of heterocyclic compounds. The resulting catalyst was used in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, polyhydroquinolines and 2-amino-6-(arylthio)pyridine-3,5-dicarbonitriles as biologically interesting compounds. The present research is focused on investigation of recycling, reusability

  一种新颖，高效，绿色的Cu（II）/ L- His @ Fe 3 O 4催化剂已成功用于杂环化合物的合成。所得催化剂用于合成2，3-二氢喹唑啉-4（1H）-酮，聚氢喹啉和2-氨基-6-（芳硫基）吡啶-3，5-二碳腈作为生物学上感兴趣的化合物。本研究的重点是研究相反应中催化剂的循环利用，可重复使用性和稳定性。Cu（II）/ L -His @ Fe 3 O 4该催化剂至少使用了六次，其活性与新鲜催化剂相当。通过TGA / DTG，EDS，XRD，VSM，FT-IR和SEM对催化剂的化学组成和结构进行了分析。
• Facile and Rapid Access to Poly Functionalized Pyridine Derivatives
  作者：Pravin V. Shinde、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1002/cjoc.201190178

  日期：2011.5

  An efficient and greener protocol for the synthesis of poly functionalized pyridines using tetra‐n‐butyl ammonium fluoride (TBAF) in water is established. Remarkable advantages of the present synthetic strategy over the others are shorter reaction times, higher isolated yields, reuse of catalytic system, simple work‐up procedure and more especially its applicability to heteryl and aliphatic aldehydes

  建立了在水中使用四正丁基氟化铵（TBAF）合成多官能吡啶的高效，绿色方案。与其他方法相比，本合成策略的显着优势是反应时间更短，分离产率更高，催化体系可重复使用，后处理步骤简单，尤其是适用于杂醛和脂族醛。
• Boric acid catalyzed convenient synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines in aqueous media
  作者：Pravin V. Shinde、Swapnil S. Sonar、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.tetlet.2009.12.146

  日期：2010.3

  A one-pot three-component condensation of an aldehyde, malononitrile, and thiophenol has been achieved by conventional and ultrasound method. The reaction has been catalyzed by boric acid in aqueous medium. This protocol afforded corresponding 2-amino-3,5-dicarbonitrile-6-thio-pyridines in shorter reaction times and high yields with the green aspects by avoiding toxic catalysts and solvents.

  醛，丙二腈和苯硫酚的一锅三组分缩合已通过常规和超声方法实现。该反应已在含水介质中被硼酸催化。通过避免有毒的催化剂和溶剂，该方案以较短的反应时间和高收率在绿色方面提供了相应的2-氨基-3,5-二碳腈-6-硫代吡啶。
• Sodium chloride: a proficient additive for the synthesis of pyridine derivatives in aqueous medium
  作者：Jitendra B. Gujar、Mahendra A. Chaudhari、Deepak S. Kawade、Murlidhar S. Shingare

  DOI：10.1016/j.tetlet.2014.10.125

  日期：2014.12

  A facile and convenient synthesis of substituted pyridine derivatives catalysed by NaCl in the presence aqueous media under reflux and ultrasound irradiation has been developed via a one-pot multicomponent reaction, in which four new bonds were formed. Particularly valuable features of this protocol including mild conditions, simple execution, broad substrate scope and good yields of products make

  通过一锅多组分反应，在一个含水的介质中，在回流和超声辐射下，在水介质中，NaCl催化的取代吡啶衍生物的便捷合成已经得到了发展，其中形成了四个新的键。该方案特别有价值的特征包括温和的条件，简单的执行，广泛的底物范围和良好的产物收率，使其成为构建吡啶骨架的有效且有前途的合成策略。
• Aqueous Suspension of Basic Alumina: An Efficient Catalytic System for the Synthesis of Poly Functionalized Pyridines
  作者：Pravin V. Shinde、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.5012/bkcs.2011.32.2.459

  日期：2011.2.20

  In the present work, catalytic activity of basic alumina in water has been demonstrated for the synthesis of poly functionalized pyridines. This strategy has some remarkable advantages, such as use of heterogeneous catalyst in aqueous media, reusability of catalyst and scalable approach.

  在目前的工作中，碱性氧化铝在水中的催化活性已被证明可用于合成多官能化吡啶。该策略具有一些显着的优势，例如在水介质中使用非均相催化剂、催化剂的可重复使用性和可扩展的方法。