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

Ibrahim Waziri, Mustafa A. Isa, Molahlehi Sonopo, D. Bradley G. Williams, Alfred Muller

Research output: Contribution to journalReview articlepeer-review

5 Citations (Scopus)

Abstract

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 μg.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 drug-likeness properties.

Original languageEnglish
Article number128381
JournalBioorganic and Medicinal Chemistry Letters
Volume52
DOIs
Publication statusPublished - 15 Nov 2021

Keywords

  • Antibiotics
  • Antimicrobial resistance
  • Bacteria
  • Cupferron

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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