2-amino-4-(thiophen-2-yl)-6-(4-methylphenylsulfanyl)-3,5-pyridinedicarbonitrile | 1373941-16-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-amino-4-(thiophen-2-yl)-6-(4-methylphenylsulfanyl)-3,5-pyridinedicarbonitrile
• 英文别名: 2-Amino-6-(4-methylphenyl)sulfanyl-4-thiophen-2-ylpyridine-3,5-dicarbonitrile
• CAS: 1373941-16-2
• 化学式: C₁₈H₁₂N₄S₂
• 分子量: 348.452
• InChiKey: BRGSZWFQIDACFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 potassium permanganate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 生成 2-amino-4-(thiophen-2-yl)-6-(4-methylphenylsulfanyl)-3,5-pyridinedicarbonitrile
  参考文献：
  名称：

  K₂CO₃-Mediated, One-Pot, Multicomponent Synthesis of Medicinally Potent Pyridine and Chromeno[2,3-b]pyridine Scaffolds

  摘要：

  An efficient one-pot, multicomponent synthesis of 3,5-dicyanopyridines has been developed from the reaction of malononitrile and different thiophenol or thiols with a variety of aldehydes (aromatic including hindered ones, heteroaromatic, and aliphatic) in the presence of 20 mol% of K2CO3 in refluxing 50% aqeuous ethanol. KMnO4 has been utilized as a readily available, inexpensive oxidant for the in situ transformation of the initially formed dihydropyridine intermediate. K2CO3 also mediates the one-pot formation of chromeno[2,3-b]pyridines from reaction of salicylaldehyde or its analogs with malononitrile and thiol or thiophenols. Both of these conditions also work equally well under 50-fold scale-up conditions.Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.555284

文献信息

• Wang resin catalyzed sonochemical synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines as potential inhibitors of SIRT1
  作者：Hemalatha Kotakommula、Vaishnavi Chintala、Satya Sree Nannapaneni、Naresh Kumar Katari、Ravikumar Kapavarapu、Manojit Pal

  DOI：10.1016/j.molstruc.2023.136756

  日期：2024.1

  these molecules was established via the 3-component reaction (3-CR) of appropriate aliphatic or (hetero)aromatic aldehyde, malononitrile and thiophenol under ultrasound. The reaction was catalyzed by the sulphonic acid-functionalized Wang resin (Wang-OSO3H) and proceeded in aqueous media under open air for 1 h to afford the desired products in 65-86% yields. The recoverability and recyclability of the

  对识别潜在抗癌药物的新方法/策略的探索促使我们关注 SIRT1，它被认为是一种新兴的癌症药理学靶点。选择 2-氨基-3,5-二甲腈-6-硫代-吡啶作为设计新的和可能的 SIRT1 抑制剂的框架。首先，在计算机上基于该框架的许多分子的对接不仅显示了它们与 SIRT1 的良好相互作用，而且表明了它们相对于 SIRT2 对该蛋白的潜在选择性。该研究还表明 VAL412、PHE414、ILE347、ALA262、ILE411、HIS363、GLN345、ASN346、ILE270、ILE316、PHE273 和 PHE297 是这些分子的常见相互作用残基，其中 VAL412 和 PHE414 主要参与氢键相互作用。通过适当的脂肪族或（杂）芳香族醛、丙二腈和苯硫酚在超声波下的三组分反应（3-CR），可以方便地获取这些分子。该反应由磺酸功能化的 Wang 树脂 (Wang-OSO 3H)并在露天的水性