Abstract

New mono aspirinate thiourea-azo derivatives 2a–f were synthesized using aspirin as a natural product-based precursor, with 4-aminophenylazophenol derivatives in excellent 70–90% yields. Overall, 2a–f gave excellent antibacterial activity against Staphylococcus aureus S48/81 and 2-(((3-((2-bromophenyl)diazenyl)-4-hydroxyphenyl)carbamothioyl)carbamoyl)phenyl acetate (2d) exhibited a larger zone of inhibition 10 mm, comparable to the standard ampicillin. The molecular docking analysis of 2d against S. aureus tyrosyl-tRNA synthetase protein displayed a free energy interaction of −7.7 kcal/mol compared to aspirin (−6.4 kcal/mol).

摘要

使用阿司匹林作为天然产物的前体合成了新的单阿斯匹林酸酯硫脲-偶氮衍生物2a-f，并以70-90％的高产率合成了4-氨基苯基偶氮苯酚衍生物。总的来说，2a–f对金黄色葡萄球菌S48 / 81具有出色的抗菌活性，而2-（（（（3-（（2-溴苯基）二氮烯基）-4-羟基苯基）氨基甲硫酰基）氨基甲酰基）苯基乙酸酯（2d）表现出较大的抑制作用10 mm，与标准氨苄西林相当。2d对金黄色葡萄球菌酪氨酰-tRNA合成酶蛋白的分子对接分析显示，与阿斯匹林相比，自由能相互作用为-7.7 kcal / mol（-6.4 kcal / mol）。