Pyrazole-hydrazone derivatives as anti-inflammatory agents: Design, synthesis, biological evaluation, COX-1,2/5-LOX inhibition and docking study

Abdelgawad, Mohamed A.; Labib, Madlen B.; Abdel‐Latif, Mahmoud

doi:10.1016/j.bioorg.2017.08.014

Cited by 64 publications

(36 citation statements)

References 32 publications

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“…Recently, novel, pyrazole-hydrazone derivatives as anti-inflammatory agents were synthesized and evaluated for their in vitro COX-1, COX-2 and 5-LOX enzymes inhibitition potential. Especially, Compound 328 (IC 50 = 0.58 lM) showed better COX-2 inhibitory activity than celecoxib (IC 50 = 0.87 lM) [ 230 ]. In search of novel anti-inflammatory motifs, several new pyrazole compounds were synthesized by Singh et al and evaluated for cyclooxygenase inhibition against recombinant human COX-2 enzyme.…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. The presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antipsychotic CDPPB, the anti-obesity drug rimonabant, difenamizole, an analgesic, betazole, a H2-receptor agonist and the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Owing to this diversity in the biological field, this nucleus has attracted the attention of many researchers to study its skeleton chemically and biologically. This review highlights the different synthesis methods and the pharmacological properties of pyrazole derivatives. Studies on the synthesis and biological activity of pyrazole derivatives developed by many scientists around the globe are reported.

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Section: Pharmacological Activitiesmentioning

confidence: 99%

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

et al. 2018

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“…According to recent papers on N ‐aryl pyrazolines, the introduction of the aryl group at the N ‐1 position of the dihydropyrazole ring leads to biological activity improvement. [ 33,45–48 ] However, chlorophenyl derivatives may enhance potency and binding efficiency compared to their unsubstituted phenyl derivatives. [ 2,49,50 ] In addition, these derivatives show an improvement in metabolic stability and pharmacokinetic profile, as recently demonstrated by Eggert et al, [ 49 ] who identified that the 3,4‐dichloro derivative (IC 50 = 0.08 μM) is more active than the corresponding 4‐chloro (IC 50 = 0.8 μM) and unsubstituted phenyl derivatives (IC 50 > 20 μM) against SMYD2 for the treatment of cancer.…”

Section: Resultsmentioning

confidence: 99%

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Cuartas

Robledo

Vélez

et al. 2020

Archiv der Pharmazie

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A new series of N-substituted pyrazoline derivatives 6a-g, 7a-g, 8a-g, and 9a-g was synthetized by reaction of hydrazine derivatives and chalcone-thiazole hybrids bearing nitrogen mustard 5a-g. The chalcones 5a-g were obtained by Claisen-Schmidt condensation of thiazole-2-nitrogen mustard 3 and selected acetophenones 4a-g. These new compounds 6/7/8/9a-g were screened for their antifungal activity against Cryptococcus neoformans, with IC 50 values of 3.9-7.8 µg/ml for the N-3, 5-dichlorophenyl pyrazolines 9e-g. Interestingly, those compounds show low cytotoxic effects toward erythrocytes (RBC). In addition, N-acetyl (6a,b) and N-formyl pyrazolines (7a, 7b, 7c, and 7g) showed inhibitory activity against methicillinsusceptible Staphylococcus aureus, methicillin-resistant S. aureus, and vancomycinintermediate S. aureus, with the most important minimum inhibitory concentration values ranging from 31.25 to 125 µg/ml. Regarding the antiprotozoal activity, thiazolyl-pyrazolines 9g, 8f, and 7c display high activity against Plasmodium falciparum, Leishmania (V) panamensis, and Trypanosoma cruzi, with EC 50 values of 11.80, 6.46, and 4.98 μM, respectively, and with 7c being approximately 2.6-fold more potent than benznidazole with a selectivity index of 1.61 on U-937 human cells, showing promising potential as a novel antitrypanosomal agent. K E Y W O R D S antibacterial activity, antifungal activity, antiprotozoal activity, chalcone, pyrazoline

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“…The gram positive Staphylococcus aureus (MTCC 1430) and gram negative bacteria Escherichia coli (MTCC 1573), were pre-cultured in agar medium in Petri dish after mixing the bacteria in distilled water. Poured it in agar medium and centrifuged it 48-72 hr at 35 o C [42,43]. Cup-plate method.…”

Section: Preparation Of Inoculumsmentioning

confidence: 99%

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

2020

Biointerface Res Appl Chem

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Synthesis of new hydrazone derivatives, starting from 2-(3, 4-Dichloro-benzoyl)-benzoic acid to 2-(3, 4-dichloro-benzoyl) - benzoic acid ethyl ester than converted into 2- (3, 4-Dichloro-benzoyl)-benzoic acid hydrazide with a substituted aldehyde. The structure of newly synthesized compounds was confirmed by analytical and spectral analysis IR, 1HNMR and MASS. For docking study, we took structures of ligand compounds (i.e. AK-series Compounds) and target protein structures into ‘pdb’ file format. Three compounds as possible anti-convulsant AK-1, AK-2 &Ak-4 were considered for compounds Ak-1 was not found suitable for anti-convulsant activity; while AK-2 & AK-4 have the capacity to show anti-convulsant activity with lesser affinity than controls. As an overall conclusion, except Ak-1, other compounds can be further used for anti- convulsant activity. Anti-convulsant activities were performed on rats by using maximal Electroshock Seizure test and minimal Neurotoxicity. Compound 2- (3, 4 – Dichloro-benzoyl)-benzoic acid (4- chloro-benzylidene) (AK-2) shows good anti-convulsant activity. The in-vitro antibacterial strains Escherichia coli MTCC 1573), and staphylococcus aureus (MTCC 1430), were used. Compound 2-(3, 4-Dichloro-benzoyl)-benzoic acid (2-notro-benzylidene-hydrazide (AK-1) gives the highest activity against Escherichia coli (MTCC 1573) and Staphylococcus aureus (MTCC-1430).

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Pyrazole-hydrazone derivatives as anti-inflammatory agents: Design, synthesis, biological evaluation, COX-1,2/5-LOX inhibition and docking study

Cited by 64 publications

References 32 publications

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

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