Synthesis, Electronic, and Antibacterial Properties of 3,7-Di(hetero)aryl-substituted Phenothiazinyl N-Propyl Trimethylammonium Salts

Molecules. 2024 May 3;29(9):2126. doi: 10.3390/molecules29092126.

Abstract

In this study, a library of 3,7-di(hetero)aryl-substituted 10-(3-trimethylammoniumpropyl)10H-phenothiazine salts is prepared. These title compounds and their precursors are reversible redox systems with tunable potentials. The Hammett correlation gives a very good correlation of the first oxidation potentials with σp parameters. Furthermore, the title compounds and their precursors are blue to green-blue emissive. Screening of the salts reveals for some derivatives a distinct inhibition of several pathogenic bacterial strains (Mycobacterium tuberculosis, Staphylococcus aureus, Escherichia coli, Aconetobacter baumannii, and Klebsiella pneumoniae) in the lower micromolar range.

Keywords: Suzuki coupling; antibacterials; biological properties; cyclic voltammetry; fluorescence; heterocycles.

MeSH terms

  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / pharmacology
  • Bacteria / drug effects
  • Escherichia coli / drug effects
  • Microbial Sensitivity Tests*
  • Molecular Structure
  • Oxidation-Reduction
  • Phenothiazines* / chemical synthesis
  • Phenothiazines* / chemistry
  • Phenothiazines* / pharmacology
  • Quaternary Ammonium Compounds / chemical synthesis
  • Quaternary Ammonium Compounds / chemistry
  • Quaternary Ammonium Compounds / pharmacology
  • Salts / chemistry
  • Salts / pharmacology
  • Staphylococcus aureus / drug effects
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Phenothiazines
  • Salts
  • Quaternary Ammonium Compounds