Synthesis, Study Antimicrobial, and Antioxidant Agents of New Tetrazole Derivatives Containing 2-Amino-5-(4-nitrophenyl)-1,3,4-thiadiazol

Abstract

Objective: The synthesis, antibacterial, and antioxidant assessment of novel tetrazole derivatives with the 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole moiety are the main objectives of this work. Methods: A multi-step procedure was used to synthesis the desired compounds, beginning with the creation of the thiadiazole core and ending with the functionalization of tetrazole rings. Results and Discussion: 2-Amino-5-(p-nitro phenyl)-1,3,4thiadiazole (I) was prepared by reacting p-nitro benzoic acid with thiosemicarbazide in the presence of POCl₃. Compound (I) then underwent a reaction with 2-chloroacetohydrazide to produce 2-(5-(4-nitrophenyl)-1,3,4thiadiazol-2-yl)acetohydrazide (II). Several new Schiff bases (IIIa–IIId) were synthesized by reacting compound (I) with different aromatic aldehydes. In contrast, tetrazole derivatives (IVa–IVd) were produced by reacting Schiff bases derivatives (IIIa–IIId) with sodium azide. NMR and infrared spectroscopy were among the spectroscopic methods used to confirm the structures of the produced compounds. Using standard disc diffusion and broth dilution techniques, the antibacterial activity of these derivatives was evaluated against a panel of Gram-positive and Gram-negative bacteria. Additionally, radical scavenging assays was used to assess the antioxidant potential. The results showed that a number of the produced tetrazole derivatives have notable antioxidant and antibacterial properties. Conclusions: These results imply that 2-amino-5-(4-nitrophenyl)-1,3,4-thiadiazole scaffold-containing tetrazole derivatives may be good candidates for the synthesis of novel medicinal medicines with combined antioxidant and antibacterial capabilities.