Synthesis, characterization and antibiotic evaluation of some novel (E)-3-(4-diphenylamino)phenyl)-1-(4′-fluorophenyl)prop-2-en-1-one chalcones and their analogues

Abstract

Abstract Background The increase in resistance of pathogenic organisms to the available chemotherapeutic agents are critical challenges in drug design and development, motivating researchers to look for novel compounds that can combat multidrug-resistant organisms. Recently, chalcones have been proved to be attractive moieties in drug discovery. Results Eight novel triphenylamine chalcones with different substitution patterns were successfully synthesized via the conventional Claisen–Schmidt condensation reaction in an alkaline medium at room temperature, and recrystallized using ethanol, the percentage yield of the compounds were between 30 and 92%. The structures of the synthesized chalcones were successfully characterized and confirmed using FT-IR, NMR spectroscopic and GC–MS spectrometric techniques. Conclusions The results of the biological studies showed that all the synthesized chalcones possess remarkable activities against the tested microbes, by showing a significant zone of inhibitions relative to that of the standard drugs used. The investigation revealed that 1b showed highest ZOI (30 mm), lowest MIC (12.5 µg/ml) and MBC/MFC (50 µg/ml) on Aspergillus niger. Therefore, displayed better antifungal potential as compared to the rest of the compounds, and can be a potential antifungal drug candidate.

Keywords

• Acetophenone
• Antibiotics
• Condensation
• Recrystallization
• Propiophenone