The present study describes the syntheses of a series of novel symmetrical bisthiadiazolines 4(a-j) built around the ten types of aliphatic/aromatic linkers. These bisheterocycles have been systematically synthesized by using the ring closure reactions of bisthiosemicarbazones 3(a-j) by refluxing under the acetic anhydride (Ac₂O) medium. The latter have been efficiently achieved through the condensation reactions of appropriate dinaphthaldehydes 2(a-j) with thiosemicarbazide in the presence of dry MeOH/HCl conditions. The treatment of 2-hydroxy-1-naphthaldehyde 1 with suitable dihalogenated reagents under the anhydrous K₂CO₃/Bu₄N⁺I⁻/dry acetone medium furnished new intermediates 2(a-j). IR, ¹H NMR, ¹³C NMR, ESI-MS & elemental analyses spectral data were in full agreement to their proposed structures. The aliphatic chains linked bisthiadiazolines 4(a-f) displayed significant antioxidant potencies while aromatic spacers based products 4(g-j) were found to exhibit better antimicrobial properties. The molecular docking simulations have also been carried out to visualize the possible interaction of most active antimicrobial compound 4g at the active sites of Staphylococcus aureus tyrosyl-tRNA synthetase protein (PdB: 1JIL).

本研究描述了围绕十种脂族/芳族连接基构建的一系列新型对称双噻二唑啉4（aj）的合成。这些双环杂环化合物是通过在乙酸酐（Ac ₂ O）介质下回流，使用双硫代半咔唑3（aj）进行闭环反应而系统合成的。在干燥的MeOH / HCl条件下，通过适当的二萘二醛2（aj）与硫代氨基脲的缩合反应可以有效地实现后者。在无水K ₂ CO ₃ / Bu ₄ N下用合适的二卤代试剂处理2-羟基-1-萘甲醛1⁺我^- /无水丙酮介质提供新的中间体2（AJ） 。红外，¹ H NMR，¹³ C NMR，ESI-MS和元素分析光谱数据与所建议的结构完全吻合。脂族链连接的双噻二唑啉4（af）显示出显着的抗氧化能力，而芳香族间隔基产品4（gj）被发现具有更好的抗菌性能。还进行了分子对接模拟，以可视化最活泼的抗菌化合物4g在金黄色葡萄球菌酪氨酰tRNA合成酶蛋白（PdB：1JIL）的活性位点的可能相互作用。