Abstract In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, including UV-visible, IR, mass spectra, and 1H- and 13C-NMR. The in situ formed diazobenzothiazole ions regiospecifically react with acetaminophen derivatives in the Hollemann-guided electrophilic aromatic substitution mechanism. The regio-orientations were established, on the one hand, by a rigorous interpretation of 1H-NMR spectra and, on the other hand, by the characteristic fragmentation patterns observed on the electrospray mass spectra. In the cases of 4a and 4b, multisubstitutions occurred. The antimicrobial activity of compound 4, along with all the starting materials, was investigated on Pseudomonas aeruginosa PA01, Staphylococcus aureus 18, Escherichia coli 64R, and S. aureus ATCC 25923. The results showed that this skeletal framework exhibited marked potency as antibacterial agents. The most active antibacterial agent against both targeted organisms was compound 4a′.

中文翻译：

---

重氮苯并噻唑离子与对乙酰氨基酚偶联反应的新型偶氮化合物的合成、特征断裂模式和抗菌活性

摘要 本研究通过取代苯并噻唑衍生物的重氮化，再与对乙酰氨基酚偶氮偶合，合成了一系列偶氮苯并噻唑染料4。使用分析数据和光谱技术确认所有合成化合物的化学结构，包括紫外可见、红外、质谱和 1H-和 13C-NMR。原位形成的重氮苯并噻唑离子在 Hollemann 引导的亲电芳香取代机制中与对乙酰氨基酚衍生物进行区域特异性反应。一方面，通过对 1H-NMR 光谱的严格解释，另一方面，通过在电喷雾质谱上观察到的特征碎裂模式，建立了区域取向。在 4a 和 4b 的情况下，发生了多重替换。化合物4的抗菌活性，连同所有起始材料，对铜绿假单胞菌 PA01、金黄色葡萄球菌 18、大肠杆菌64R 和金黄色葡萄球菌 ATCC 25923 进行了研究。结果表明，这种骨架框架作为抗菌剂表现出显着的效力。对两种目标生物最有效的抗菌剂是化合物 4a'。