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Sulfonamides are important compounds with special applications in pharmaceuticals due to their antibacterial and antiparasitic properties, and they are known as sulfa drugs (SDs). In this study, we focused on the multifunctional therapeutic compound sulfathiazole (ST) and investigated its hybridization of imine bonds with various azo compounds. A series of novel azoimino-sulfathiazoles (AIST) was successfully synthesized using a one-pot three-component reaction (3MCR) methodology. Additionally, we reported the design and synthesis of two ST derivatives bound to an azo group in a 3MCR dish. The structure of the newly synthesized AISD after separation and purification was examined and confirmed by TLC, M.P., FT-IR, 1H NMR, and 13C NMR. Furthermore, their cytotoxicity was evaluated via MTT assay. The antibacterial, antioxidant, and anticancer activities of the AISD compounds were assessed using the MTT assay, focusing on the PC-3 human prostate cancer cell line. The results showed good resistance to E. coli and S. aureus, with inhibition zones of 27 and 31 mm, respectively, compared to standard penicillin G. More importantly, certain AIST compounds exhibited superior antibacterial activity compared to penicillin G. To understand the mode of action of the proteins and potential interactions, docking calculations were performed using the target proteins 1FDW, 3FC2, and 5GWK. 5GWK achieved the highest placement score, followed by 1FDW and 3FC2, which showed strong closeness. A detailed analysis of the ligand–protein interactions revealed the strongest interaction with human topoisomerase II alpha (5GWK) as the target protein. [ABSTRACT FROM AUTHOR]

[Display omitted] • New AZO-TZD derivatives (1–11) were synthesized using CSA as a catalyst. The compounds were studied by molecular docking. • A solvatochromic effects with electron-withdrawing and electron-donating substituent investigated. • Computational analysis of molecular geometry, optoelectronic properties, and ionization potential was conducted. • The role of different solvents, substituents, and the donor and acceptor properties of the synthesized compounds considered. • UV–visible spectrum analysis, shows acceptor–donor-acceptor characteristics resembling an organic field-effect transistor OFETs. Here, new AZO-TZD derivatives (1−11) were synthesized using cellulose sulphuric acid (CSA) as a catalyst to prepare diazonium salts and Knoevenagel condensation to produce final products. The prepared dyes were characterized by various methods including UV–Vis, FT-IR, MS, NMR spectroscopic techniques, X-ray diffraction analysis (XRD) and elemental analysis to perform detailed structure elucidation. Then, in another attempt, solvatochromic absorption was studied using different solvents. Also, the effects of substituent with electron-withdrawing and electron-donating groups at their o -, m -, and p -position were investigated. To access a deeper understanding of molecular properties, computational analysis of molecular geometry, optoelectronic properties, and ionization potential was performed. The purpose of the calculations is to clarify the role of different solvents, substituents and donor and acceptor characteristics of the connected rings in the synthesized compounds. Analysis of the UV–Vis spectrum confirmed that these molecules have acceptor–donor-acceptor characteristics that resemble an organic field effect transistor (OFET). In other efforts to evaluate their use as antibacterial, anticancer and anti-Alzheimer agents and their interaction with four different types of enzymes, such as carotenoid dehydrosqualene synthase (PDB ID: 3ACX, gram-positive), aromatase (PDB Id: 4GL7) and acetylcholinesterase (PDB) Id: 7AIX), through UDP-3-O-Acyl- N -Acetylglucosamine Deacetylase (PDB ID: 5U39, gram-negative) and their anticancer docking calculations were investigated. [ABSTRACT FROM AUTHOR]