Design, synthesis, and antibacterial activity of<i>N</i>-(trifluoromethyl)phenyl substituted pyrazole derivatives

Saleh, Ibrahim A.; Kc, Hansa Raj; Roy, Subrata; Abugazleh, Mohd Kotaiba; Ali, Hashim M.; Gilmore, David F.; Alam, Mohammad A.

doi:10.1039/d1md00230a

Cited by 22 publications

(12 citation statements)

References 22 publications

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“…The Hantzsch ester in refluxing toluene without any catalyst was the best reducing agent for this reaction. In our previous studies, we found that lipophilic substituents on the aniline moiety showed potent activity against bacterial strains. − Therefore, we focused on the lipophilic substituents on the aniline moiety in this report (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

Development and Antibacterial Properties of 4-[4-(Anilinomethyl)-3-phenylpyrazol-1-yl]benzoic Acid Derivatives as Fatty Acid Biosynthesis Inhibitors

Roy,

KC,

Roberts

et al. 2023

J. Med. Chem.

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A number of novel pyrazole derivatives have been synthesized, and several of these compounds are potent antibacterial agents with minimum inhibitory concentrations as low as 0.5 μg/mL. Human cell lines were tolerant to these lead compounds, and they showed negligible hemolytic effects at high concentrations. These bactericidal compounds are very effective against bacterial growth in both planktonic and biofilm contexts. Various techniques were applied to show the inhibition of biofilm growth and eradication of preformed biofilms by lead compounds. Potent compounds are more effective against persisters than positive controls. In vivo studies revealed that lead compounds are effective in rescuing C. elegans from bacterial infections. Several methods were applied to determine the mode of action including membrane permeability assay and SEM micrograph studies. Furthermore, CRISPRi studies led to the determination of these compounds as fatty acid biosynthesis (FAB) inhibitors.

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Section: Results and Discussionmentioning

confidence: 99%

Development and Antibacterial Properties of 4-[4-(Anilinomethyl)-3-phenylpyrazol-1-yl]benzoic Acid Derivatives as Fatty Acid Biosynthesis Inhibitors

Roy,

KC,

Roberts

et al. 2023

J. Med. Chem.

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“…Our studies showed that the positive control used in MIC tests, vancomycin, was not effective in eradicating the tested biofilms. These studies are very significant, as S. aureus biofilms are very challenging to treat with the existing antibiotics [ 32 ]. Similarly, E. faecalis readily forms biofilms, which are recalcitrant to existing treatments [ 33 ].…”

Section: Resultsmentioning

confidence: 99%

“…Biofilm inhibition and eradication assays were performed as described previously [ 32 ]. In brief for biofilm inhibition assay, overnight bacterial culture was suspended to 0.5 McFarland standard in sterile PBS, which was then diluted 1:1000 in cation adjusted Muller Hilton Broth (CAMHB) supplemented with 1% glucose.…”

Section: Methodsmentioning

confidence: 99%

Development of 4-[4-(Anilinomethyl)-3-phenyl-pyrazol-1-yl] Benzoic Acid Derivatives as Potent Anti-Staphylococci and Anti-Enterococci Agents

Gilmore

Alam

2022

Antibiotics

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From a library of compounds, 11 hit antibacterial agents have been identified as potent anti-Gram-positive bacterial agents. These pyrazole derivatives are active against two groups of pathogens, staphylococci and enterococci, with minimum inhibitory concentration (MIC) values as low as 0.78 μg/mL. These potent compounds showed bactericidal action, and some were effective at inhibiting and eradicating Staphylococcus aureus and Enterococcus faecalis biofilms. Real-time biofilm inhibition by the potent compounds was studied, by using Bioscreen C. These lead compounds were also very potent against S. aureus persisters as compared to controls, gentamycin and vancomycin. In multiple passage studies, bacteria developed little resistance to these compounds (no more than 2 × MIC). The plausible mode of action of the lead compounds is the permeabilization of the cell membrane determined by flow cytometry and protein leakage assays. With the detailed antimicrobial studies, both in planktonic and biofilm contexts, some of these potent compounds have the potential for further antimicrobial drug development.

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“…Overall, this study contributes to the growing list of studies that have sought to combat antimicrobial resistance with new small compounds. [45][46][47][48][49][50][51][52][53]…”

Section: Discussionmentioning

confidence: 99%

Synthesis and antibacterial activity of 2-benzylidene-3-oxobutanamide derivatives against resistant pathogens

Sood¹,

Kesavan²

2023

RSC Med. Chem.

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Design, synthesis, and antibacterial activity ofN-(trifluoromethyl)phenyl substituted pyrazole derivatives

Abstract: Design and synthesis of N-(trifluoromethyl)phenyl substituted pyrazole derivatives and their potency as antimicrobial agents are described.

Cited by 22 publications

References 22 publications

Development and Antibacterial Properties of 4-[4-(Anilinomethyl)-3-phenylpyrazol-1-yl]benzoic Acid Derivatives as Fatty Acid Biosynthesis Inhibitors

Development and Antibacterial Properties of 4-[4-(Anilinomethyl)-3-phenylpyrazol-1-yl]benzoic Acid Derivatives as Fatty Acid Biosynthesis Inhibitors

Development of 4-[4-(Anilinomethyl)-3-phenyl-pyrazol-1-yl] Benzoic Acid Derivatives as Potent Anti-Staphylococci and Anti-Enterococci Agents

Synthesis and antibacterial activity of 2-benzylidene-3-oxobutanamide derivatives against resistant pathogens

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