Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents

Bandgar, B. P.; Gawande, Shrikant S.; Bodade, Ragini G.; Gawande, Nalini M.; Khobragade, Chandrahasya N.

doi:10.1016/j.bmc.2009.10.035

Cited by 236 publications

(121 citation statements)

References 19 publications

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“…7 For instance, the inclusion of two hydroxyl groups (dihydroxychalcones) enhanced both the antitumor and lipidic antiperoxidation activities. 8 Other activities have already been reported [9][10][11] and Figure 2 shows some examples of biologically active chalcones.…”

Section: Introductionmentioning

confidence: 75%

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Silva¹,

Andrade²,

Napolitano³

et al. 2013

J. Braz. Chem. Soc.

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O presente trabalho descreve as atividades antibacterianas e antifúngicas de diversas chalconas obtidas diretamente através da condensação aldólica tipo Claisen-Schmidt das quais se determinou a concentração inibitória mínima frente a diferentes microrganismos (bactérias Gram-positivas e Gram-negativas e fungos). Estruturas no estado sólido cristalino de sete chalconas foram determinadas por análise de difração de raios X (XRD). Estudos quimiométricos foram realizados com intuito de identificar uma potencial relação entre estrutura e atividade.The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structureactivity relationship.

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Section: Introductionmentioning

confidence: 75%

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Silva¹,

Andrade²,

Napolitano³

et al. 2013

J. Braz. Chem. Soc.

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“…in THP-1 cells was measured according to the method described by Bandgar et al [27] During assay, THP-1 cells were cultured with penicillin and streptomycin (100 U/mL) and inoculated with 10% …”

Section: Cytotoxicity Assaymentioning

confidence: 99%

Antioxidant, anti‐inflammatory, and enzyme inhibitory activity of natural plant flavonoids and their synthesized derivatives

Nile

Keum

Nile

et al. 2017

J Biochem & Molecular Tox

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The synthesized flavonoid derivatives were examined for their antioxidant, anti-inflammatory, xanthine oxidase (XO), urease inhibitory activity, and cytotoxicity. Except few, all the flavonoids under this study showed significant antioxidant activity (45.6%-85.5%, 32.6%-70.6%, and 24.9%-65.5% inhibition by DPPH, ferric reducing/antioxidant power, and oxygen radical absorption capacity assays) with promising TNF-inhibitory activity (42%-73% at 10 M) and IL-6 inhibitory activity (54%-81% at 10 M) compared with that of control dexamethasone. The flavonoidsO 7 -hexyl chrysin, showed an inhibition with IC 50 values (4.5-8.1 g/mL), more than allopurinol (8.5 g/mL) at 5 M against XO and showing more than 50% inhibition at a final concentration (5 mM) with an IC 50 value of ranging from 4.8 to 7.2 ( g/mL) in comparison with the positive control thiourea (5.8 g/mL) for urease inhibition. Thus, the flavonoid derivatives may be considered as potential antioxidant and antigout agents.

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“…Their 1 H-NMR spectra showed the -CH=CH-protons as a multiplet in the 7.52-7.63 ppm range for compound 3, and two doublet peaks at 7.54, 7.60 and 7.48, 7.60 ppm with coupling constants of 15.3 Hz for compounds 2 and 4, respectively. The 13 C-NMR spectrum of prototypical compound 2 showed the two carbonyl carbons at 187.8 and 192.7 ppm.…”

Section: Preparation Of the Chalcones 2-4mentioning

confidence: 99%

“…Many pyrazole derivatives are reported to have a broad spectrum of biological activities, such as anti-inflammatory [13], antifungal [14], antiviral [15], cytotoxic [12], A3 adenosine receptor antagonists [16], antioxidant [13], antihypertensive [17], tranquilizing, muscle relaxant, psychoanaleptic, hypnotic, ulcerogenic, antidepressant, antibacterial and analgesic effects [18]. Pharmacologically-interesting heterocyclic systems like pyrazolines have been widely studied owing to their pharmacological activities, which include anti-tumor [19,20], anti-inflammatory [21][22][23][24][25][26][27][28][29][30][31][32], anti-parasitary [33], anticonvulsant [34], antimicrobial [35][36][37][38][39], antinociceptives [40], antimalarial [41], nitric oxide synthase inhibitory, associated with diseases such as Alzheimer, Huntington, and inflammatory arthritis [42], antidepressant [43,44], anticancer [45][46][47], antibacterial [48], antitubercular, analgesic [49], antiviral [46], antioxidant [50], antiamoebic …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives

Hassan

2013

Molecules

126

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A series of 2-pyrazolines 5-9 have been synthesized from α,β-unsaturated ketones 2-4. New 2-pyrazoline derivatives 13-15 bearing benzenesulfonamide moieties were then synthesized by condensing the appropriate chalcones 2-4 with 4-hydrazinyl benzenesulfonamide hydrochloride. Ethyl [1,2,4] Condensation of 6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbaldehyde (1') with compound 24 or 25 afforded the corresponding Schiff's bases 36 and 37, respectively. Reaction of the Schiff's base 37 with benzoyl hydrazine or acetic anhydride afforded benzohydrazide derivative 39 and the cyclized compound 40, respectively. Furthermore, the pyrazole derivatives 42-44 were synthesized by cyclization of hydrazine derivative 25 with the prepared chalcones 2-4. All the newly synthesized compounds have been characterized on the basis of IR and 1 H-NMR spectral data as well as physical data.Antimicrobial activity against the organisms E. coli ATCC8739 and P. aeruginosa ATCC 9027 as examples of Gram-negative bacteria, S. aureus ATCC 6583P as an example of Gram-positive bacteria and C. albicans ATCC 2091 as an example of a yeast-like fungus have been studied using the Nutrient Agar (NA) and Sabouraud Dextrose Agar (SDA) diffusion methods. The best performance was found for the compounds 16, 17, 19 and 20.

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Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents

Cited by 236 publications

References 19 publications

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

Antioxidant, anti‐inflammatory, and enzyme inhibitory activity of natural plant flavonoids and their synthesized derivatives

Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives

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