4-4-(Anilinomethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-ylbenzoic acid derivatives as potent anti-gram-positive bacterial agents

Hansa, Raj Kc.; Khan, Mahbub Kabir; Frangie, Melissa M; Gilmore, David F.; Shelton, Robert S.; Savenka, Alena V.; Basnakian, Alexei G.; Shuttleworth, S.L.; Smeltzer, Mark S.; Alam, Mohammad A.

doi:10.1016/j.ejmech.2021.113402

Cited by 21 publications

(25 citation statements)

References 34 publications

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“…Based on the activities, we found a good Structure Activity Relationship (SAR) of the product with respect to the substituents in the aniline moiety. The presence of a protic substituent, carboxylic acid, eliminated the activity of the compounds ( 12 and 13 ), which is in accordance with our previous findings [ 29 , 31 , 32 ]. The presence of lipophilic substituents (clog P = 7–8) on the phenyl ring of the aniline moiety increased the activity.…”

Section: Resultssupporting

confidence: 92%

“…The designed compounds were synthesized by the reaction of 3′,5′-bis(trifluoromethyl)acetophenone ( I ) with 4-hydrazinobenzoic acid ( II ) to form the hydrazone intermediate, which on reaction with the Vilsmeier-Haack reagent formed the pyrazole aldehyde ( III ) [ 21 , 29 , 30 , 31 ]. This aldehyde intermediate ( III ) was synthesized on a 10 g scale, and the pure product was obtained simply by filtration and washing with water.…”

Section: Resultsmentioning

confidence: 99%

“…As previously reported, the MIC values of the substances were calculated using the standard microdilution technique suggested by the Clinical and Laboratory Standards Institute (CLSI) [ 36 ]. Compounds were dissolved in dimethyl sulfoxide (DMSO) to achieve a starting concentration of 32 µg/mL as described by us previously [ 29 , 31 ]. Compounds were further diluted two-fold across the 96-well honeycomb plate columns in cation adjusted Mueller Hinton broth (CAMHB), and bacterial culture was added.…”

Section: Methodsmentioning

confidence: 99%

“…The human embryonic kidney cell line (HEK-293) was used to assess the cytotoxicity of the antibiotics as described by us previously [ 29 , 31 ]. HEK-293 cells were cultured in Dulbecco’s modified eagle’s medium (DMEM) containing 10% Fetal Bovine Serum (FBS) and incubated at 37 °C in the presence of 5% carbon dioxide.…”

Section: Methodsmentioning

confidence: 99%

“…A number of widely used drugs, such as dutasteride [ 26 ], hydroxyflutamide [ 27 ], and cinacalcet [ 28 ], contain the trifluoromethyl substituted phenyl moiety ( Figure 1 ). We have found the trifluoromethyl substituted phenyl groups as potent growth inhibitors of different bacterial strains, including MRSA [ 22 , 29 ]. Based on the significance of the trifluoromethyl group in drug discovery, herein, we report the synthesis and antimicrobial activities of 3,5-bis(trifluoromethyl)phenyl substituted pyrazole derivatives as potent antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 3,5-Bis(trifluoromethyl)phenyl-Substituted Pyrazole Derivatives as Potent Growth Inhibitors of Drug-Resistant Bacteria

Alkhaibari

Roy

et al. 2021

Molecules

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Enterococci and methicillin-resistant S. aureus (MRSA) are among the menacing bacterial pathogens. Novel antibiotics are urgently needed to tackle these antibiotic-resistant bacterial infections. This article reports the design, synthesis, and antimicrobial studies of 30 novel pyrazole derivatives. Most of the synthesized compounds are potent growth inhibitors of planktonic Gram-positive bacteria with minimum inhibitory concertation (MIC) values as low as 0.25 µg/mL. Further studies led to the discovery of several lead compounds, which are bactericidal and potent against MRSA persisters. Compounds 11, 28, and 29 are potent against S. aureus biofilms with minimum biofilm eradication concentration (MBEC) values as low as 1 µg/mL.

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Section: Resultssupporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of 3,5-Bis(trifluoromethyl)phenyl-Substituted Pyrazole Derivatives as Potent Growth Inhibitors of Drug-Resistant Bacteria

Alkhaibari

Roy

et al. 2021

Molecules

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Design, Synthesis, Docking Study of Pyrazolohydrazinopyrimidin‐4‐one Derivatives and Their Application as Antimicrobials

Bakr

Alolyyan

Elkanzi

et al. 2023

Chemistry & Biodiversity

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New series of pyrazoles 4a-c and pyrazolopyrimidines 5a -f had been constructed. The newly synthesized compounds were assessed for their antimicrobial activity towards E. coli and P. aeruginosa (gram -ve bacteria), B. subtilis and S. aureus (gram + ve bacteria) and A. flavus and C. albicans (representative of fungi). The pyrazolylpyrimidine-2,4-dione derivative 5b is the most active candidate against B. subtilis (MIC = 60 μg/mL) and P. aeruginosa (MIC = 45 μg/mL). Regarding antifungal potential, compound 5f was the most effective against A. flavus (MIC = 33 μg/mL). Similarly, compound 5c displayed strong antifungal activity towards C. Albicans (MIC = 36 μg/mL) in reference to amphotericin B (MIC = 60 μg/mL). Finally, the novel compounds had been docked inside dihydropteroate synthase (DHPS) to suggest the binding mode of these compounds.

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Pyrazole‐Clubbed Piperazinyl Urea Derivatives: Synthesis, Characterization and Antimicrobial Studies toward Generating an Antibiotic/Antifungal Resistance Sensor

et al. 2023

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An efficient and practically feasible synthesis of a series of novelpyrazole-clubbed piperazinyl urea derivatives and screening results of their antimicrobial activity along with currentvoltage studies of selected compounds were reported. The reaction of (1,3-diaryl-1H-pyrazol-4-yl)(piperazin-1yl)methanone hydrochlorides with various cycloalkyl/aryl isocyanates under basic condition afforded the formation of target compounds in good to excellent yield. The intermediate compounds 8a,b were synthesized in several steps by the method reported in the literature. The novel synthesized compounds were characterized by various spectroscopic techniques such as IR, 1 H NMR, 13 C NMR and mass spectra. All the novel urea derivatives have been screened for their antimicrobial activity and some of the derivatives exhibit significant activity against bacterial and fungal isolates. Further current-voltage (IV) studies were also performed on selected compounds to see the feasibility for generating futuristic antibiotic/antifungal resistance sensor.

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4-4-(Anilinomethyl)-3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-ylbenzoic acid derivatives as potent anti-gram-positive bacterial agents

Cited by 21 publications

References 34 publications

Synthesis of 3,5-Bis(trifluoromethyl)phenyl-Substituted Pyrazole Derivatives as Potent Growth Inhibitors of Drug-Resistant Bacteria

Synthesis of 3,5-Bis(trifluoromethyl)phenyl-Substituted Pyrazole Derivatives as Potent Growth Inhibitors of Drug-Resistant Bacteria

Design, Synthesis, Docking Study of Pyrazolohydrazinopyrimidin‐4‐one Derivatives and Their Application as Antimicrobials

Pyrazole‐Clubbed Piperazinyl Urea Derivatives: Synthesis, Characterization and Antimicrobial Studies toward Generating an Antibiotic/Antifungal Resistance Sensor

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