In this work, the synthesis of 16 novel compounds generated through condensation reactions employing o-phenylenediamine, o-aminophenol and o-aminothiol is carried out. The synthesized products comprised derivatives of benzimidazole-2-thione, benzoxazole-2-thione and benzothiazole-2-thione, obtained in yields ranging from 70% to 90%. Structural elucidation was performed using nuclear magnetic resonance spectroscopy, Fourier-transform infrared spectroscopy and high-resolution mass spectrometry. In addition, the study investigated the ADMET properties and dynamic molecular behaviour of the synthesized compounds. Significantly, this work introduces a novel synthetic strategy for generating derivatives of 2-mercapto-benzimidazole, 2-mercaptobenzoxazole and 2-mercaptobenzothiazole, providing valuable understanding of their chemical structures and underlying formation pathways. Furthermore, the inhibitor activity of these molecules against HIV and HSV viruses was assessed using a docking method as an alternative to traditional laboratory experiments, enhancing the efficiency of antiviral screening.