Synthesis of heterocyclic Diazenyl derivatives and their metal complexes: Exploring antioxidant, antimicrobial potential and in silico targeting of diabetes related enzymes

Abstract

The increasing resistance to conventional drugs has demanded effective drugs. In the current study, a series of diazenyl derivatives, 3-amino-2-chloropyridine (SC8-SC14), were synthesized by the diazotization method, and their metal (Cu⁺², Fe⁺², Ni⁺²) complexes were synthesized by complexation reaction under reflux with pH control. The stability and characteristics of the synthesized complexes were confirmed through comprehensive analytical techniques, including FTIR, NMR, Mass, UV–Vis, TGA, XRD, molar conductivity, Job's method, elemental analysis, and EPR spectroscopies. The antioxidant (DPPH and NO), antimicrobial, and molecular docking potential of the synthesized compounds were evaluated. Furthermore, the derivative (SC8) possessed potent antioxidant activity (IC₅₀ = 4.59 μg/mL) comparable with ascorbic acid (IC₅₀ = 2.16 μg/mL). Gram-positive (Staphylococcus Pyogenes and Bacillus) and gram-negative (E. coli and Pseudomonas) microorganisms were used to measure antibacterial activities, MIC, and MBC measurements. Whereas Amikacin was used as a standard drug. Molecular docking with proteins Oligo-1,6-glucosidase (3AJ7) and Mannosyl-oligosaccharide glucosidase (4J5T) was performed. The SC8 shows excellent binding energies of −8.5 and − 8.6 kcal/mol for Mannosyl-oligosaccharide glucosidase (4J5T) and Oligo-1,6-glucosidase (3AJ7), respectively. These findings show that these compounds have therapeutic potential for use in the field of medicinal chemistry.