Bak Andrzej, Kozik Violetta, Swietlicka Aleksandra, Baran Wojciech, Smolinski Adam, Zięba Andrzej
Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland.
Department of General and Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200 Sosnowiec, Poland.
Pharmaceuticals (Basel). 2023 Jul 9;16(7):984. doi: 10.3390/ph16070984.
The multistep synthesis of novel -terephthalthioamides based on methyl esters of amino acids (AAs) was proposed using conventional heating and microwave-assisted approaches. In fact, the comparative case study on the thionation of new symmetrical diamides with Lawesson's reagent (LR) was performed. The microwave-accelerated small-scale methodology was successfully employed on the whole pathway from substrates (Gly, Ala, Val, Tyr, Ser) to products (symmetrical dithioamides of terephthalic acid), resulting in significantly reduced reaction time, energy requirements, and slightly increased reaction yields when compared to conventional heating. Moreover, the intermolecular similarity of novel terephthalic acid derivatives was estimated in the multidimensional space (mDS) of the structure/property-related in silico descriptors using principal component analysis (PCA) and hierarchical clustering analysis (HCA). The distance-oriented structure/property distribution was also correlated with the experimental lipophilic data.
提出了基于氨基酸（AAs）甲酯的新型对苯二甲硫酰胺的多步合成方法，采用传统加热和微波辅助方法。事实上，进行了用劳森试剂（LR）对新型对称二酰胺进行硫代反应的对比案例研究。从底物（甘氨酸、丙氨酸、缬氨酸、酪氨酸、丝氨酸）到产物（对苯二甲酸的对称二硫酰胺）的整个过程中，成功采用了微波加速小规模方法，与传统加热相比，反应时间显著缩短，能量需求降低，反应产率略有提高。此外，使用主成分分析（PCA）和层次聚类分析（HCA）在与结构/性质相关的计算机描述符的多维空间（mDS）中估计了新型对苯二甲酸衍生物的分子间相似性。面向距离的结构/性质分布也与实验亲脂性数据相关。
