Polarographic and electrochemical studies of some aromatic and heterocyclic nitro compounds, part II: Polarographic and voltammetric reduction of some nitramines, pyrazolium, and imidazolium nitro derivatives

Dumanović, D.; Jovanović, Jovan; Sužnjević, Desanka Ž.; Erceg, M.; Zuman, P.

doi:10.1002/elan.1140040809

Cited by 12 publications

(8 citation statements)

References 11 publications

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“…Under anaerobic conditions or low oxygen pressure, the reduction process is similar to that observed for nitrobenzene 4 . The reduction mechanism for several aromatic and heterocyclic nitrocompounds was presented by Zuman and co-workers [5][6][7][8][9][10][11][12][13] . A total of two electrons and two protons is involved in the formation of the nitroso (R-NO) intermediate, two more electrons and protons result in the hydroxylamine (R-NHOH) [5][6][7][8][9][10][11][12][13][14] In voltammetric studies of nitroimidazole derivatives [15][16][17] , two reduction waves were observed in aqueous acid medium.…”

Section: Introductionmentioning

confidence: 99%

Voltammetric Behaviour of Metronidazole at Mercury Electrodes

La-Scalea¹,

Serrano²,

Gutz³

1999

J. Braz. Chem. Soc.

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Metronidazol é o fármaco mais importante do grupo de 5-nitroimidazoles, possuindo toxicidade contra microrganismos anaeróbicos, sendo a molécula de DNA o principal alvo de sua ação biológica. O mecanismo de ação do metronidazol depende do processo de redução do grupo nitro e, em meio ácido, a redução é pH-dependente envolvendo quatro elétrons na completa redução ao derivado hidroxilamínico. Em meio aprótico a redução do metronidazole acontece em duas etapas: a primeira envolvendo um elétron para formar o radical nitro e a segunda etapa envolve mais três elétrons até a formação da hidroxilamina. Neste artigo o mecanismo de redução do metronidazol foi estudado utilizando as técnicas voltamétricas: polarografia d.c. e pulso diferencial, voltametria cíclica usando o eletrodo gota de mercúrio como eletrodo de trabalho. Metronidazole is the most important drug of the group of 5-nitroimidazoles and possesses toxicity to anaerobic microorganisms DNA being the main target for their biological action. The mechanism of biological action of metronidazole is dependent upon the nitro group reduction process. The reduction of metronidazole is pH dependent in acid medium and four electrons are involved in the complete reduction to the hydroxylamine derivative. In aprotic medium the reduction of the metronidazole occurs in two steps, the first involving one electron to form the nitro radical and the second step involving three more electrons until the formation of the hydroxylamine derivative. In this paper the mechanism of reduction of metronidazole was studied by using the voltammetric techniques: d.c. polarography, differential pulse polarography and cyclic voltammetry using the mercury drop as the working electrode.

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Section: Introductionmentioning

confidence: 99%

Voltammetric Behaviour of Metronidazole at Mercury Electrodes

La-Scalea¹,

Serrano²,

Gutz³

1999

J. Braz. Chem. Soc.

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“…9,10 Theories which deal more quantitatively with electron transfer, adiabatic or non-adiabatic, are described elsewhere. [9][10][11] It is important to stress that in organic electrochemical reactions and in biochemical processes, a strong coupling between electron and proton transfer 2,6,10,11 occurs, and these couplings make the reduction mechanism much more complex.…”

Section: Theoretical Backgroundmentioning

confidence: 99%

“…The first synthesized nitro compound was nitrobenzene, which was synthesized by the Mitscherlich reaction 1 in 1884, and it was also the first organic compound studied by the polarographic technique. [1][2][3] After the year 1925, many organic, especially nitro compounds, have been studied electrochemically [2][3][4][5][6] and for many of them the mechanisms of their reduction were explained. Since many nitrodiazoles are pharmaceutically active compounds, the understanding of the reduction process of these compounds is crucial for basic medicinal chemistry, as well as for the pharmaceutical industry.…”

Section: Introductionmentioning

confidence: 99%

“…From the very beginning, these compounds have found many applications. They have been used as chemotherapeutics (antibacterial, antitrichomonal and antihistomonal (antiriprotozoal) agents 6 ) and as radiosensitizers in medical practice. The capability of nitrodiazoles to bind to DNA and block their replication 4,7,8 could have many applications in antiviral therapy.…”

Section: Introductionmentioning

confidence: 99%

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Molecular-orbital and structural descriptors in theoretical investigation of electroreduction of nitrodiazoles

Kolarić

Juranić

Dumanović

2005

JSCS

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It is shown how a simple theoretical approach can be used for the investigation of electro-organic reactions.Mononitroimidazoles and mononitropyrazoles were studied by the semiempirical MNDO-PM3 molecular orbital method. The electrochemical reduction potentials of diazoles have been correlated with the energy of the lowest unoccupied molecular orbital (LUMO). It was found that an admirable correlation could be obtained by the introduction of simple structural descriptors as a correction to the energy of the LUMO. The interaction of a molecule with its surrounding depends on electrostatic potential and on steric hindrance. Most of these steric effects are taken into account using two parameters having a very limited set of integer values. The first (?) is the position of a ring substituent regarding ring nitrogens, which accounts for the different orientations of dipole moments and for the different shape of the electrostatic potential. The second (structural) parameter (?) is the type of the ring, which accounts mostly for different modes of electrode approach, and for different charge polarization patterns in two diazole rings. The extended correlation with ELUMO, ? and ?, is very good, having a regression coefficient r = 0.991. The intrinsic importance of ? and ? is exemplified by their high statistical weight.

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“…Ova pojava je verovatno posledica promene sporog stupnja u procesu redukcije, kao što je već ranije zapaženo od strane više istraživača[107][108][109][110][111][112][113][114][115][116][117][118][119][120]. Koeficijent pravca E 1/2 -pH krive za drugi talas je 71 mV/pH (slika 25A, kriva…”

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Contribution to the Characterisation and Determination of some Neonicotinoids

Gužvanj¹

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Polarographic and electrochemical studies of some aromatic and heterocyclic nitro compounds, part II: Polarographic and voltammetric reduction of some nitramines, pyrazolium, and imidazolium nitro derivatives

Cited by 12 publications

References 11 publications

Voltammetric Behaviour of Metronidazole at Mercury Electrodes

Voltammetric Behaviour of Metronidazole at Mercury Electrodes

Molecular-orbital and structural descriptors in theoretical investigation of electroreduction of nitrodiazoles

Contribution to the Characterisation and Determination of some Neonicotinoids

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