Synthesis, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones

Miguel, Fábio Balbino; Dantas, Juliana A.; Amorim, Stefany; Andrade, Gustavo F. S.; Costa, Luiz Antônio S.; Couri, Mara R.C.

doi:10.1016/j.saa.2015.07.041

Cited by 17 publications

(11 citation statements)

References 40 publications

(42 reference statements)

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“…Chalcones, pyrazolines and pyrazoles were prepared according to the method previously described 36 , 37 . The chemical structures of all compounds are presented in Figs.…”

Section: Methodsmentioning

confidence: 99%

Pyrazoline derivatives as promising novel antischistosomal agents

Morais

Mengarda

Miguel

et al. 2021

Sci Rep

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Praziquantel is the only available drug to treat schistosomiasis, a parasitic disease that currently infects more than 240 million people globally. Due to increasing concerns about resistance and inadequate efficacy there is a need for new therapeutics. In this study, a series of 17 pyrazolines (15–31) and three pyrazoles (32–34) were synthesized and evaluated for their antiparasitic properties against ex vivo adult Schistosoma mansoni worms. Of the 20 compounds tested, six had a 50% effective concentration (EC50) below 30 μM. Our best hit, pyrazoline 22, showed promising activity against adult schistosomes, with an EC50 < 10 µM. Additionally, compound 22 had low cytotoxicity, with selectivity index of 21.6 and 32.2 for monkey and human cell lines, respectively. All active pyrazolines demonstrated a negative effect on schistosome fecundity, with a marked reduction in the number of eggs. Structure–activity relationship analysis showed that the presence of the non-aromatic heterocycle and N-substitution are fundamental to the antischistosomal properties. Pharmacokinetics, drug-likeness and medicinal chemistry friendliness studies were performed, and predicted values demonstrated an excellent drug-likeness profile for pyrazolines as well as an adherence to major pharmaceutical companies’ filters. Collectively, this study demonstrates that pyrazoline derivatives are promising scaffolds in the discovery of novel antischistosomal agents.

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“…Chalcones, pyrazolines and pyrazoles were prepared according to the method previously described 36 , 37 . The chemical structures of all compounds are presented in Figs.…”

Section: Methodsmentioning

confidence: 99%

Pyrazoline derivatives as promising novel antischistosomal agents

Morais

Mengarda

Miguel

et al. 2021

Sci Rep

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“…Researchers have been driven to manufacture many laser dyes to avoid these drawbacks. These synthesized materials are distinguished by their ease of synthesis, as well as their distinctive properties [ 8 , 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Spectral Characteristics and Molecular Structure of (E)-1-(4-Chlorophenyl)-3-(4-(Dimethylamino)Phenyl)Prop-2-en-1-One (DAP)

Aldaghri

2021

Materials

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In this work, a laser dye of (E)-1-(4-chlorophenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one (DAP) was synthesized and examined as a new laser medium. The compound DAP’s photophysical properties were investigated under the influence of solvents, concentrations, and pump power excitations. The absorption spectra showed a single band, and the shape of the spectra remained the same, regardless of the optical density. The fluorescence spectra showed a band around 538 nm; its intensity was inversely proportional to the concentration. DAP exhibits dual amplified spontaneous emission (ASE) bands at 545 and 565 nm under suitable pump power laser excitation and concentration. The results revealed that the ASE band at 565 nm is affected by solvents polarity, concentrations and pump power energies. This band could be attributed to the combination of two excited molecules and the solvent between them (superexciplex). Moreover, the molecular structure, the energy bandgap, and the total energy of DAP was calculated using density functional theory.

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“…Derivatives containing the 2-pyrazoline moiety have been reported to have diverse biological activities such as antimalarial, antimicrobial, antituberculosis, antioxidant, anti-inflammatory, anticancer, anti-microbial, anti-parasitary, antidepressive and anticonvulsant properties (Karad et al, 2016). Many researchers have reported various routes for their synthesis; the most common one is by condensation of α,β-unsaturated carbonyl compound with hydrazine derivatives (Miguel et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Anticonvulsant evaluation of 2-pyrazolines carrying naphthyl moiety: An insight into synthesis and molecular docking study

Nusrat

Siddiqui

Sahu

et al. 2019

Braz. J. Pharm. Sci.

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A series of N-substituted-3-(napthalen-2-yl)-5-substituted phenyl-4,5-dihydropyrazole-1-carbothioamide derivatives (4a-n) were synthesized with the view of structural requirements of pharmacophore for potential anticonvulsant agents. The synthesized compounds were assayed intraperitoneally (i.p.) and subcutaneously (s.c.) in mice against seizures induced by MES and scPTZ methods, respectively. Neurologic deficit was evaluated by rotarod method. Among the tested compounds, 4g, 4i, 4j and 4n emerged as the most active molecule in the MES model at a dose of 30 mg/kg at 0.5h comparable to standardscarbamazepine and phenytoin. In the scPTZ test,4e and 4l were found to be most active compounds at the lowest dose of 30 mg/kg at 0.5h, in the management of the convulsive disorder. Molecular docking studies of the titled compounds were also donewith 3D crystal structure of human cytosolic branched chain amino transferase (hBCATc) enzyme and compound 4e was found to have five hydrogen bond interactions with the most important active site residues.In neurotoxicity studies, except compounds 4b, 4c, 4h and 4k, rest of the compounds showed no sign of toxicity.

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Synthesis, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones

Cited by 17 publications

References 40 publications

Pyrazoline derivatives as promising novel antischistosomal agents

Pyrazoline derivatives as promising novel antischistosomal agents

Spectral Characteristics and Molecular Structure of (E)-1-(4-Chlorophenyl)-3-(4-(Dimethylamino)Phenyl)Prop-2-en-1-One (DAP)

Anticonvulsant evaluation of 2-pyrazolines carrying naphthyl moiety: An insight into synthesis and molecular docking study

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