Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives

Bacterial resistance to antimicrobial agents is increasing at an alarming rate globally and requires new lead compounds for antibiotics. In this study, N-phenyl-N-nitroso hydroxylamine (cupferron) and its derivatives have been synthesised using readily available starting materials. The compounds were obtained in high yield and purity. They show activity towards a range of Gram-positive and Gram-negative pathogenic bacteria, with minimum inhibitory concentration (MIC) values as low as 2 mu g.mL-1 against the tested organisms, especially for Gram-positive species. Toxicity studies on the lead compound 3b indicate insignificant effects on healthy cell lines. Molecular docking studies on the lead compound identify possible binding modes of the compound, and the results obtained correlate with those of in vitro and MIC studies. The lead compound shows excellent druglikeness properties.

Automated summary

The study synthesized N-phenyl-N-nitroso hydroxylamine and its derivatives, which showed activity against a range of bacteria, particularly Gram-positive species. Toxicity studies on the lead compound indicated insignificant effects on healthy cell lines. Molecular docking studies helped identify possible binding modes of the compound and confirmed results obtained from in vitro and MIC studies.