Abstract The present work established the synthesis of novel azo incorporated heterocyclic bioactive compounds (4a-4d) via diazo-coupling reaction between the 2-amino benzothiazole and various synthetic phenolic antioxidant molecules like BHA, phloroglucinal, 2,4-di‑tert-butylphenol and 2,6-di‑tert-butylphenol. The structure of newly synthesized azo compounds was confirmed by various spectroscopic techniques such as UV–Vis, FT-IR, 1H NMR, 13C NMR and LC-(ESI)MS while a single crystal X-ray structural analysis of the azo compound (4a) was carried out. Biological efficiency of novel azo compounds was evaluated by antioxidant activities like DPPH radical scavenging activity and reducing power activity which exhibits the azo compounds 4a and 4b possess potent antioxidant ability. The significant antibacterial activity also exposed by all newly synthesized azo compounds against human pathogenic organisms and often the remarkable activity also observed by 4a and 4b in all bacterial strain. In silico molecular docking study demonstrates the azo fused compounds owing several crucial interactions with EGFR protein. Moreover in vitro anticancer and toxicity of selected azo compounds were assessed by MTT cytotoxicity assay against lung cancer cell line (A549) and normal skin cell line (L929).

中文翻译：

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与苯并噻唑稠合的新型生物活性偶氮化合物的合成和表征及其多功能生物应用

摘要 目前的工作通过 2-氨基苯并噻唑与各种合成酚类抗氧化剂分子（如 BHA、间苯三酚、2,4-二叔丁基苯酚）之间的重氮偶联反应建立了新型偶氮杂环生物活性化合物（4a-4d）的合成。和 2,6-二叔丁基苯酚。新合成的偶氮化合物的结构通过各种光谱技术证实，如紫外-可见光、红外光谱、1H NMR、13C NMR和LC-(ESI)MS，而偶氮化合物(4a)的单晶X射线结构分析) 进行。新型偶氮化合物的生物效率通过抗氧化活性如DPPH自由基清除活性和还原力活性来评估，显示出偶氮化合物4a和4b具有强大的抗氧化能力。所有新合成的偶氮化合物对人类病原生物也具有显着的抗菌活性，4a 和 4b 在所有菌株中也经常观察到显着的活性。计算机分子对接研究表明，偶氮稠合化合物与 EGFR 蛋白有几个关键的相互作用。此外，通过对肺癌细胞系 (A549) 和正常皮肤细胞系 (L929) 的 MTT 细胞毒性测定，评估了所选偶氮化合物的体外抗癌和毒性。