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A series of mono-substituted thiourea ( 2a–i ) and  bis -substituted thiourea-azo ( 3a–f)  derived from paracetamol derivatives were prepared from isothiocyanates with one and two equivalents of halogenated azo dyes, respectively. The incorporation of azo-derived paracetamol  via  thiourea moiety in  2a–i  depicted excellent microbial activity on  Staphylococcus aureus , and 2-(((3-((2-bromophenyl)diazenyl)-4-hydroxyphenyl)carbamothioyl)carbamoyl)phenyl acetate,  2a  showed equivalent inhibition properties to the standard ampicillin (10 mm). The structure–activity relationship studies of  2a  were supported  via  molecular docking interaction against  S. aureus  tyrosyl-tRNA synthetase protein which displayed a free energy interaction of −7.7 kcal/mol compared to aspirin (−6.4 kcal/mol).

phosphorus, sulfur, and silicon and the related elements

Synthesis and structure–activity relationship studies of mono- and  bis -thiourea derivatives featuring halogenated azo dyes with antimicrobial properties