Synthesis and structural characterization of some novel methoxyamino derivatives with acid-base and redox behavior

Bem, Marioara; Baratoiu, Rodica Daniela; Radutiu, C.; Lete, Cecilia; Mocanu, Sorin; Ioniţă, Gabriela; Lupu, Stelian; Cãproiu, Miron Teodor; Mădălan, Augustin M.; Patrascu, Bianca; Zarafu, Irina; Ioniță, Petre

doi:10.1016/j.molstruc.2018.06.114

Cited by 6 publications

(5 citation statements)

References 17 publications

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“…Following our interest and experience in methoxyaminyl [22] and hydrazyl free radicals [18], we aimed to synthesize two new compounds, derived from dansyl chloride, presuming that they can be easily converted into pro-fluorescent persistent free radicals. Thus, dansyl chloride in reaction with 1,1-diphenylhydrazine or methoxyamine afforded the expected compounds 1 and 2 ( Figure 3).…”

Section: Synthesis Of Dansyl Derivatives 1 and 2 And Structural Charamentioning

confidence: 99%

“…In time, 3 slowly decomposes, as shown by the intensity of the ESR spectrum (about 10% in 30 min); TLC analysis showed formation of a myriad of compounds. By oxidation of 2 in the same conditions, no direct ESR signal could be detected; however, it is presumed that the corresponding unstable free radical 4 was formed (as for many similar compounds, the ESR spectra are showed in the literature [7,17,22]). Employing the ESR spin-trapping technique and using t-butyl-α-phenyl nitrone (PBN) as a spin-trap, it was possible to capture the methoxy free radical as a by-product.…”

Section: Formation Of Free Radicalsmentioning

confidence: 99%

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Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

Patrascu

Mocanu²,

Coman

et al. 2020

IJMS

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Starting from dansyl-chloride, in reaction with 1,1-diphenylhydrazine and methoxyamine, two new fluorescent derivatives 1 and 2 were obtained and characterized by NMR, IR, UV-Vis, HR-MS, and fluorescence spectroscopy. The single-crystal X-ray structure was obtained for compound 2. Both compounds generate free radicals by oxidation, as demonstrated by ESR spectroscopy. Compound 1 generates the corresponding hydrazyl-persistent free radical, evidenced directly by ESR spectroscopy, while compound 2 generates in the first instance the methoxyaminyl short-lived free radical, which decomposes rapidly with the formation of the methoxy radical, evidenced by the ESR spin-trapping technique. By oxidation of compounds 1 and 2, their fluorescence is quenched.

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Section: Synthesis Of Dansyl Derivatives 1 and 2 And Structural Charamentioning

confidence: 99%

Section: Formation Of Free Radicalsmentioning

confidence: 99%

Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

Patrascu

Mocanu²,

Coman

et al. 2020

IJMS

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“…As a continuation of our previous work [3], we have used the previously synthesised eight derivatives of 3,5-dinitro-4-methoxyamino-benzoic acid (Figure 2), containing moieties with well-known biological effects (like phenazone (antipyrine) and benzocaine), for further biological characterization. Experimental and calculated hydrophobicity together with the total antioxidant capacity were measured before [3].…”

Section: Figurementioning

confidence: 99%

“…Alcoxy-aminyl persistent free radicals are a class of compounds discovered in the 60' and intensively studied due to their peculiar properties [1][2][3][4][5][6] such as their stability towards oxygen, lack of dimerization, as well as unusual physical and chemical properties (e.g.,their intense colour that changes with pH) [7]. The most well-known derivatives are of N-alkoxyand N-picrylaminyls type and were studied mainly by means of electron spin resonance (ESR) and electronic absorption spectra [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Bioevaluation of the Antimicrobial and Anti-Proliferative Potential of Some Derivatives of 3,5-Dinitro-4-Methoxyamino-Benzoic Acid

Zarafu¹

2020

FARMACIA

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The purpose of this study was to evaluate the anti-proliferative and antimicrobial activity of some derivatives of 3,5-dinitro-4-methoxyamino-benzoic acid previously obtained by coupling reactions of the above mentioned acid with benzylamine, nbutylamine, 4-amino-antipyrine, benzocaine, 3,4-dimethyl-5-amino-isoxazole, 3,4-dimethoxyphenyl-2-ethylamine and the corresponding methyl ester. The anti-tumoural activity was investigated on HCT8 cells, while the antimicrobial one was tested on bacterial and fungal cells, in planktonic and adherent growth state. The obtained compounds exhibited good antimicrobial activity, both against free-living, planktonic, as well as biofilm embedded Gram-positive bacterial and fungal cells, as well as anti-proliferative activity on the HCT8 cells. While PZ2, PZ6 and PZ7 compounds have shown a remarkable effect against planktonic microbial cells, PZ4 and PZ7 proved to be the most active anti-biofilm compounds. Considering their anti-tumoural potential, PZ1 and PZ7 proved to be the most cytotoxic against the HCT8 cells, inducing the HCT8 cells apoptosis and arrest in the G2/M phase of the cellular cycle. RezumatScopul acestui studiu a fost evaluarea activității antimicrobiene și anti-proliferative a unor derivați ai acidului 3,5-dinitro-4metoxiamino-benzoic obținuți anterior prin reacții de cuplare ale acidului mai sus menționat cu benzilamina, n-butilamina, 4 amino-antipirina, benzocaina, 3,4-dimetil-5-amino-isoxazolul, 3,4-dimetoxifenil-2-etilamina și esterul metilic corespunzător. Activitatea antitumorală a fost investigată pe celule HCT8, iar cea antimicrobiană față de celule bacteriene și fungice, în fază de creștere planctonică și aderată. Compușii obținuți au manifestat o bună activitate antimicrobiană, atât față de celulele bacteriene Gram-pozitive și fungice, aflate în suspensie, planctonice, precum și față de celulele încorporate în biofilm și de asemenea, au prezentat activitate anti-proliferativă față de celulele HCT8. În timp ce compușii PZ2, PZ6 și PZ7 au manifestat un efect deosebit față de celulele microbiene planctonice, PZ4 și PZ7 s-au dovedit a fi citotoxici față de celulele HCT8, inducând apoptoza acestora și blocarea în faza G2/M a ciclului celular.

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“…where Abs i is the initial absorbance of the mixture and the Abs 30 min is the absorbance measured after 30 min ( Remes et al., 2012 ; Paun et al., 2013 ; Bem et al., 2018 ).…”

Section: Methodsmentioning

confidence: 99%

Repurposing anti-inflammatory drugs for fighting planktonic and biofilm growth. New carbazole derivatives based on the NSAID carprofen: synthesis, in silico and in vitro bioevaluation

Dumitrascu,

Caira,

Avram

et al. 2023

Front. Cell. Infect. Microbiol.

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IntroductionOne of the promising leads for the rapid discovery of alternative antimicrobial agents is to repurpose other drugs, such as nonsteroidal anti-inflammatory agents (NSAIDs) for fighting bacterial infections and antimicrobial resistance.MethodsA series of new carbazole derivatives based on the readily available anti-inflammatory drug carprofen has been obtained by nitration, halogenation and N-alkylation of carprofen and its esters. The structures of these carbazole compounds were assigned by NMR and IR spectroscopy. Regioselective electrophilic substitution by nitration and halogenation at the carbazole ring was assigned from H NMR spectra. The single crystal X-ray structures of two representative derivatives obtained by dibromination of carprofen, were also determined. The total antioxidant capacity (TAC) was measured using the DPPH method. The antimicrobial activity assay was performed using quantitative methods, allowing establishment of the minimal inhibitory/bactericidal/biofilm eradication concentrations (MIC/MBC/MBEC) on Gram-positive (Staphylococcus aureus, Enterococcus faecalis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) strains. Computational assays have been performed to assess the drug- and lead-likeness, pharmacokinetics (ADME-Tox) and pharmacogenomics profiles.Results and discussionThe crystal X-ray structures of 3,8-dibromocarprofen and its methyl ester have revealed significant differences in their supramolecular assemblies. The most active antioxidant compound was 1i, bearing one chlorine and two bromine atoms, as well as the CO2Me group. Among the tested derivatives, 1h bearing one chlorine and two bromine atoms has exhibited the widest antibacterial spectrum and the most intensive inhibitory activity, especially against the Gram-positive strains, in planktonic and biofilm growth state. The compounds 1a (bearing one chlorine, one NO2 and one CO2Me group) and 1i (bearing one chlorine, two bromine atoms and a CO2Me group) exhibited the best antibiofilm activity in the case of the P. aeruginosa strain. Moreover, these compounds comply with the drug-likeness rules, have good oral bioavailability and are not carcinogenic or mutagenic. The results demonstrate that these new carbazole derivatives have a molecular profile which deserves to be explored further for the development of novel antibacterial and antibiofilm agents.

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Synthesis and structural characterization of some novel methoxyamino derivatives with acid-base and redox behavior

Cited by 6 publications

References 17 publications

Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors

Bioevaluation of the Antimicrobial and Anti-Proliferative Potential of Some Derivatives of 3,5-Dinitro-4-Methoxyamino-Benzoic Acid

Repurposing anti-inflammatory drugs for fighting planktonic and biofilm growth. New carbazole derivatives based on the NSAID carprofen: synthesis, in silico and in vitro bioevaluation

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