Schuylkill Campus, Pennsylvania State University, 200 University Drive, Schuylkill Haven, PA 17972, USA.
Department of Chemistry, Pennsylvania State University, 104 Chemistry Building, Room 08, University Park, State College, PA 16802, USA.
Molecules. 2021 Oct 9;26(20):6099. doi: 10.3390/molecules26206099.
A series of fourteen 2-aryl-3-phenyl-2,3-dihydro-4-pyrido[3,2-][1,3]thiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of -phenyl--aryl imines with thionicotinic acid, two difficult substrates. The reactions were operationally simple, did not require specialized equipment or anhydrous solvents, could be performed as either two or three component reactions, and gave moderate-good yields as high as 63%. This provides ready access to -phenyl compounds in this family, which have been generally difficult to prepare. As part of the study, the first crystal structure of neutral thionicotinic acid is also reported, and showed the molecule to be in the form of the thione tautomer. Additionally, the synthesized compounds were tested against the causative agent of Human African Sleeping Sickness. Screening at 50 µM concentration showed that five of the compounds strongly inhibited growth and killed parasites.
我们在室温下通过 T3P 介导的 -苯基亚苯基亚胺与硫代烟酰胺的环化反应，简便地合成了一系列 14 个 2-芳基-3-苯基-2,3-二氢-4-吡啶并[3,2-][1,3]噻嗪-4-酮，这两种都是难合成的底物。该反应操作简单，不需要特殊设备或无水溶剂，可以作为两或三组分反应进行，最高产率可达 63%。这为合成该家族的 -苯基化合物提供了便利，因为这些化合物通常很难制备。作为研究的一部分，还报道了中性硫代烟酰胺的第一个晶体结构，结果表明该分子是以硫酮互变异构体的形式存在。此外，合成的化合物还针对引起人类昏睡病的病原体进行了筛选。在 50µM 浓度下进行筛选，结果表明有 5 种化合物强烈抑制了寄生虫的生长并杀死了寄生虫。
