2-amino-4-(thiophen-2-yl)-6-[(4-chlorophenyl)sulfanyl]pyridine-3,5-dicarbonitrile

• 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-chlorophenyl)sulfanyl]pyridine-3,5-dicarbonitrile
• 英文别名: 2-Amino-6-(4-chlorophenyl)sulfanyl-4-thiophen-2-ylpyridine-3,5-dicarbonitrile
• 化学式: C₁₇H₉ClN₄S₂
• 分子量: 368.87
• InChiKey: UBNXMKPGDJTAIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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 air 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-amino-4-(thiophen-2-yl)-6-[(4-chlorophenyl)sulfanyl]pyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  合成和评价针对朊病毒病的吡啶二腈重点文库。

  摘要：

  我们报告了一组 55 种吡啶二甲腈作为潜在的朊病毒疾病治疗剂的制备和筛选。使用微波辐照来改进合成通常只会导致产率的小幅提高，但会产生更清洁的反应，从而促进产物的分离。通过表面等离子共振分析该文库与人朊病毒蛋白 (huPrPC) 的结合以及抑制其在小鼠脑细胞 (SMB) 中形成的部分蛋白酶抗性同种型 PrPSc。共有 26 种化合物被发现与 huPrPC 结合，而 12 种显示出可辨别的 PrPSc 形成抑制作用，发现 5 种在 2.5-9microwo 范围内显示 EC(50) 的化合物相对于未处理的对照将 PrPSc 水平降低至 30% 以下50纳米。

  DOI：

  10.1016/j.ejmech.2007.02.018

文献信息

• K₂CO₃-Mediated, One-Pot, Multicomponent Synthesis of Medicinally Potent Pyridine and Chromeno[2,3-b]pyridine Scaffolds
  作者：Sarita Mishra、Rina Ghosh

  DOI：10.1080/00397911.2011.555284

  日期：2012.8.1

  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.
• Mechanistic studies leading to a new procedure for rapid, microwave assisted generation of pyridine-3,5-dicarbonitrile libraries
  作者：Kai Guo、Mark J. Thompson、Tummala R.K. Reddy、Roger Mutter、Beining Chen

  DOI：10.1016/j.tet.2007.03.139

  日期：2007.6

  Mechanistic investigations into the multi-component synthesis of pyridine-3,5-dicarbonitriles have established a defined reaction pathway, particularly clarifying the role of aerobic oxidation in conversion of the intermediate 1,4-dihydropyridines into the final products. Based on such improved understanding of the reaction mechanism, optimised conditions for the preparation of compound libraries based on this core structure have been developed and represent a significant improvement in yield over existing protocols. Particularly, microwave assisted synthesis was found to provide a procedure suitable for high-throughput synthesis of pyridine-3,5-dicarbonitrile libraries. (c) 2007 Elsevier Ltd. All rights reserved.