2-amino-4-(2-naphthyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile | 1153740-44-3

• 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-(2-naphthyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile
• 英文别名: 2-Amino-4-(2-naphthyl)-6-phenylsulfanyl-pyridine-3,5-dicarbonitrile；2-amino-4-naphthalen-2-yl-6-phenylsulfanylpyridine-3,5-dicarbonitrile
• CAS: 1153740-44-3
• 化学式: C₂₃H₁₄N₄S
• 分子量: 378.457
• InChiKey: BKECABSTHKSCLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-萘甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-amino-4-(2-naphthyl)-6-(phenylsulfanyl)pyridine-3,5-dicarbonitrile
  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

• 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）。
• 2-Hydroxyethylammonium acetate: A reusable task-specific ionic liquid promoting one-pot, three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines
  作者：Sara Sobhani、Moones Honarmand

  DOI：10.1016/j.crci.2012.10.011

  日期：2013.3

  Abstract 2-Hydroxyethylammonium acetate (2-HEAA) as a task-specific ionic liquid, efficiently promotes one-pot three-component reaction of aryl/heteroaryl/alkyl aldehydes with aryl/alkyl thiols and malononitrile at room temperature. This protocol offers several advantages such as using a reusable and cost-effective ionic liquid, being amenable to scale-up and produces the corresponding 2-amino-3,5

  摘要 2-羟基乙基乙酸铵（2-HEAA）作为一种任务特异性离子液体，在室温下可有效促进芳基/杂芳基/烷基醛与芳基/烷基硫醇和丙二腈的一锅三组分反应。该协议提供了几个优点，例如使用可重复使用且具有成本效益的离子液体，易于放大并在短时间内（5 分钟）生产相应的 2-amino-3,5-dicarbonitrile-6-thio-pyridines ) 并且收益良好。
• Unique role of 2-hydroxyethylammonium acetate as an ionic liquid in the synthesis of Fe3O4 magnetic nanoparticles and preparation of pyridine derivatives in the presence of a new magnetically recyclable heterogeneous catalyst
  作者：Sara Sobhani、Fatemeh Nasseri、Farzaneh Zarifi

  DOI：10.1007/s13738-018-1460-6

  日期：2018.12

  environmentally friendly synthesis of Fe3O4 nanoparticles by a co-precipitation method. The synthesized Fe3O4 nanoparticles were used as solid material for supporting 2-HEAA (Fe3O4-2-HEAA). The newly prepared Fe3O4-2-HEAA was characterized by TEM, XRD, FT-IR, TGA and elemental analysis and successfully applied as a magnetically recyclable heterogeneous catalyst for the efficient one-pot, three-component synthesis

  摘要本文采用乙酸2-羟乙基铵（2-HEAA）作为第一种功能化离子液体，通过共沉淀法轻松，经济和环保地合成Fe 3 O 4纳米粒子。合成的Fe 3 O 4纳米颗粒用作支撑2-HEAA（Fe 3 O 4 -2-HEAA）的固体材料。新制备的Fe 3 O 4通过TEM，XRD，FT-IR，TGA和元素分析对-2-HEAA进行了表征，并成功地将其用作可磁循环的多相催化剂，用于高效地一锅，三组分合成2-氨基-3,5-二甲腈- 6-硫代吡啶。催化剂很容易被外磁体分离，并重复使用至少五次而活性没有明显降低。 图形概要
• Ionic liquid immobilized on γ-Fe2O3 nanoparticles: A new magnetically recyclable heterogeneous catalyst for one-pot three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines
  作者：Sara Sobhani、Moones Honarmand

  DOI：10.1016/j.apcata.2013.08.006

  日期：2013.10

  2-Hydroxyethylammonium sulphonate immobilized on gamma-Fe2O3 nanoparticles (gamma-Fe2O3-2-HEAS) was synthesized as a new supported ionic liquid by the reaction of n-butylsulfonated gamma-Fe2O3 with ethanolamine. It was used as a magnetically recyclable heterogeneous catalyst for the efficient one-pot, three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines. The catalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least five times without significant degradation in the activity. (C) 2013 Elsevier B.V. All rights reserved.
• 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.