Background Antibiotic resistance has risen as a result of a variety of conditions, prompting researchers to look for new compounds that can combat multidrug-resistant organisms. Over the last two decades, chalcones have been proved to be attractive moieties in drug discovery. Various substituted acetophenones, propiophenones and 4-(Diphenylamino) benzaldehyde were combined, using the Aldol condensation reaction to obtain eight novel triphenylamine chalcones. The compound’s antimicrobial properties were investigated (in vitro). With the non-mutant X-ray Human cytochrome P450 21A2 Hydroxyprogesterone retrieved from Protein Data Bank (PDB: 5VBU), molecular docking experiments were also carried out to analyse the most favourable conformation and find the orientation that maximizes interaction and minimize energy. Results Eight novel triphenylamine chalcones were successfully synthesized and recrystallized using ethanol, the percentage yield of the compounds were between 30 and 92%. The activity against different pathogens revealed that, all synthesized compounds showed marked antimicrobial activity against the tested microorganisms. (E)-3-(4-(diphenylamino)phenyl)-1-(3′-nitrophenyl)prop-2-en-1-one (1b) showed the highest zone of inhibition against Aspergillus niger, measuring 30 mm. The minimum inhibitory concentration (MIC) results revealed that (E)-1-(4′-bromophenyl)-3-(4-(diphenylamino)phenyl)prop-2-en-1-one (1a), (E)-3-(4-(diphenylamino)phenyl)-1-(3′-nitrophenyl)prop-2-en-1-one (1b), (E)-1-(4′-chlorophenyl)-3-(4-diphenylamino)phenyl)prop-2-en-1-one (1c), (E)-3-(4-diphenylamino)phenyl)-1-(4′-fluorophenyl)prop-2-en-1-one (1d) and (E)-4-(3-(diphenylamino)phenyl)-1-(4-fluorophenyl)-2-methylbut-3-en-1-one (2d) had the lowest MIC and inhibit Aspergillus niger growth at 12.5 µg/ml. All the synthesized compounds showed minimum bactericidal concentration and minimum fungicidal concentration (MBC/MFC) effect against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Candida albicans and Aspergillus niger at 50 µg/ml. The docking studies of the synthesized chalcones with the binding site of the Human cytochrome P450 21A2 Hydroxyprogesterone (PDB: 5VBU) reveal that the binding affinity of the synthesized chalcones was in the range of − 11.2 to − 9.4 kcal/mol and showed highest binding score compared to that of the standard drugs (Fluconazole and Ciproflaxacin), with docking scores of − 7.9 and − 7.3 kcal/mol, respectively. Conclusions The investigation reveals that compound 1b showed the highest ZOI of 30 mm, least MIC and MBC/MFC of 12.5 and 50 µg/ml against Aspergillus niger, respectively. Therefore, displayed better antifungal potential as compared to the rest of the compounds. The outcome of the docking analysis revealed that (E)-4-(3-(diphenylamino)phenyl)-1-(4′-hydroxyphenyl)-2-methylbut-3-en-1-one (2a) showed a better binding affinity of -11.2 kcal/mol, which is higher than the remaining compounds and the control drugs (fluconazole and ciproflaxacin).
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.
Our search for new antibiotics led to the syntheses and biological evaluation of new classes of dicarboxylic acid analogues. The syntheses involve nucleophilic addition of different substituted benzylamine, aniline, alkylamine, and 4-hydroxyl-L-proline with carbamoylbenzoic acid. The results of the antimicrobial activity as indicated by the zone of inhibition (ZOI) showed that Z 10 is the most active against Pseudomonas aeruginosa (32 mm) and least active against Candida stellatoidea (27 mm) and Vancomycin Resistant Enterococci (VRE) (27 mm), while Z 7 shows the least zone of inhibition (22 mm) against Methicillin Resistant Staphylococcus aureus (MRSA). The minimum inhibition concentration (MIC) determination reveals that Z 10 inhibits the growth of tested microbes at a low concentration of 6.25 μg/mL, while Z 9 and Z 12 inhibits the growth of most microbes at a concentration of 12.5 μg/mL, recording the least MIC. The Minimum Bactericidal/Fungicidal Concentration (MBC/MFC) results revealed that Z 10 has the highest bactericidal/fungicidal effect on the test microbes, at a concentration of 12.5 μg/mL, with the exception of Candida stellatoidea and Vancomycin Resistant Enterococci (VRE) with MBC/MFC of 25 μg/mL. The result of this investigation reveals the potential of the target compounds (Z 1–3,5,7–12) in the search for new antimicrobial agents.
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