Microwave Assisted Synthesis and Spectroscopic Characterization of Some Novel Schiff Bases of Carprofen Hydrazide

Bordei, Alexandra Teodora

doi:10.31925/farmacia.2019.6.4

Cited by 8 publications

(9 citation statements)

References 17 publications

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“…Recently, we reported in our previous papers the synthesis and structural, biological and bioinformatics characterization of new derivatives based on carprofen scaffolds [20][21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives

et al. 2022

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The efficient regioselective bromination and iodination of the nonsteroidal anti-inflammatory drug (NSAID) carprofen were achieved by using bromine and iodine monochloride in glacial acetic acid. The novel halogenated carprofen derivatives were functionalized at the carboxylic group by esterification. The regioselectivity of the halogenation reaction was evidenced by NMR spectroscopy and confirmed by X-ray analysis. The compounds were screened for their in vitro antibacterial activity against planktonic cells and also for their anti-biofilm effect, using Gram-positive bacteria (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and Gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853). The cytotoxic activity of the novel compounds was tested against HeLa cells. The pharmacokinetic and pharmacodynamic profiles of carprofen derivatives, as well as their toxicity, were established by in silico analyses.

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Section: Introductionmentioning

confidence: 99%

In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives

et al. 2022

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“…The syntheses of compounds 3 and 4 have been presented previously [10]. 6) (Mr 287,737; 0.001 mol) and various aromatic aldehydes (0.001 mol) was introduced into a microwave tube using 3 mL absolute methanol as the reaction medium, then a few drops of glacial acetic acid were added as a catalyst.…”

Section: Chemistrymentioning

confidence: 99%

“…The properties of these compounds result in potential applications in medicine. Compared to ordinary Schiff bases, hydrazonic N-acyl compounds are more stable and have a stronger biological activity because oxygen and nitrogen atoms could be involved in the formation of hydrogen bonds in biochemical systems [ 10 ]. Through structural modulations of the carprofen molecule, we obtained its derivatives, N-acyl hydrazones, which contain the azomethine (C=N) functional group of Schiff bases, aiming to study their potential in Alzheimer’s disease.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioinformatic Characterization of New Schiff Bases with Possible Applicability in Brain Disorders

et al. 2021

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(1) Background: The research aims to find new treatments for neurodegenerative diseases, in particular, Alzheimer’s disease. (2) Methods: This article presents a bioinformatics and pathology study of new Schiff bases, (EZ)-N′-benzylidene-(2RS)-2-(6-chloro-9H-carbazol-2-yl)propanehydrazide derivatives, and aims to evaluate the drug-like, pharmacokinetic, pharmacodynamic and pharmacogenomic properties, as well as to predict the binding to therapeutic targets by applying bioinformatics, cheminformatics and computational pharmacological methods. (3) Results: We obtained these Schiff bases by condensing (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanehydrazide with aromatic aldehydes, using the advantages of microwave irradiation. The newly synthesized compounds were characterized spectrally, using FT-IR and NMR spectroscopy, which confirmed their structure. Using bioinformatics tools, we noticed that all new compounds are drug-likeness features and may be proposed as potentially neuropsychiatric drugs (4) Conclusions: Using bioinformatics tools, we determined that the new compound 1e had a high potential to be used as a good candidate in neurodegenerative disorders treatment.

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“…N-acyl hydrazones are more stable than ordinary Schiff bases and are obtained by condensing a hydrazide with a carbonyl compound. They may also have a more pronounced biological activity than ordinary Schiff bases, because they may form hydrogen bonds with biochemical systems through oxygen and nitrogen atoms [3]. New 6-phenyl substituted derivatives of N'-(E)-(methylidene)-2-methylpyridine-3-carbohydrazide were synthesized and tested for antibacterial activity on Staphylococcus aureus, Enterococcus faecalis, Escherichia.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Study of Derivatives of (Ez)-N’- Benzylidene-(2rs)-2-(6-Chloro-9h-Carbazol-2-Yl) Propanohydrazide

TELEHOIU¹

2022

FARMACIA

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This study aims to complete the molecular characterization of some compounds with the original structure, derivatives of (EZ) -N'-benzylidene-(2RS) -2-(6-chloro-9H-carbazol-2-yl) propanohydrazide, by HR-MS and thermal analysis. The results of the antimicrobial action tests are also presented. The tests were performed on two Gram-negative bacterial strains (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853), two Gram-positive bacterial strains (Staphylococcus aureus ATCC 25923 and Enterococcus faecalis ATCC 29212) and one fungal strain (Candida albicans ATCC 10231) and including qualitative and quantitative tests, being also determined the anti-biofilm activity. Compounds 1a, 1d and 1b exhibited good in vitro antimicrobial activity, with a MIC (minimum inhibitory concentration) value of 0.31 mg/mL against Gram-positive bacterial and fungal strain. The results also indicated that the compounds are more potent against microbial biofilms. RezumatAcest studiu își propune să completeze caracterizarea moleculară a unor compuși cu structură originală, derivați ai (EZ)-N'benziliden-(2RS)-2-(6-cloro-9H-carbazol-2-il) propanohidrazidei prin analiză spectrală HR-MS și analiză termică. Sunt prezentate și rezultatele testării acțiunii antimicrobiane. Testele au fost efectuate pe două tulpini de bacterii Gram negative (Escherichia coli ATCC 25922 și Pseudomonas aeruginosa ATCC 27853), două tulpini de bacterii Gram pozitive (Staphylococcus aureus ATCC 25923 și Enterococcus faecalis ATCC 29212) și o tulpină fungică (Candida albicans ATCC 10231), utilizând metode de testare calitative și cantitative, fiind determinată inclusiv activitatea anti-biofilm. Compușii 1a, 1d și 1b au prezentat o activitate antimicrobiană bună in vitro, cu o valoare CMI (concentrație minimă inhibitorie) de 0,31 mg/mL împotriva bacteriilor Gram pozitive și a tulpinii fungice. Rezultatele au indicat, de asemenea, că acești compuși sunt mai activi împotriva biofilmelor microbiene.

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Microwave Assisted Synthesis and Spectroscopic Characterization of Some Novel Schiff Bases of Carprofen Hydrazide

Cited by 8 publications

References 17 publications

In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives

In Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives

Synthesis and Bioinformatic Characterization of New Schiff Bases with Possible Applicability in Brain Disorders

Recent Advances in the Study of Derivatives of (Ez)-N’- Benzylidene-(2rs)-2-(6-Chloro-9h-Carbazol-2-Yl) Propanohydrazide

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