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Int. J. Mol. Sci. 2012, 13(6), 7594-7606; doi:10.3390/ijms13067594

Density Functional Theory (DFT) Study of Edaravone Derivatives as Antioxidants

1,2,3,* , 1
Received: 18 May 2012 / Revised: 9 June 2012 / Accepted: 11 June 2012 / Published: 20 June 2012
(This article belongs to the Special Issue Advances in Molecular Electronic Structure Calculations)
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Quantum chemical calculations at the B3LYP/6–31G* level of theory were employed for the structure-activity relationship and prediction of the antioxidant activity of edaravone and structurally related derivatives using energy (E), ionization potential (IP), bond dissociation energy (BDE), and stabilization energies (∆Eiso). Spin density calculations were also performed for the proposed antioxidant activity mechanism. The electron abstraction is related to electron-donating groups (EDG) at position 3, decreasing the IP when compared to substitution at position 4. The hydrogen abstraction is related to electron-withdrawing groups (EDG) at position 4, decreasing the BDECH when compared to other substitutions, resulting in a better antioxidant activity. The unpaired electron formed by the hydrogen abstraction from the C–H group of the pyrazole ring is localized at 2, 4, and 6 positions. The highest scavenging activity prediction is related to the lowest contribution at the carbon atom. The likely mechanism is related to hydrogen transfer. It was found that antioxidant activity depends on the presence of EDG at the C2 and C4 positions and there is a correlation between IP and BDE. Our results identified three different classes of new derivatives more potent than edaravone.
Keywords: edaravone derivatives; ionization potential; bond dissociation energies; antioxidant; DFT edaravone derivatives; ionization potential; bond dissociation energies; antioxidant; DFT
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Borges, R.S.; Queiroz, A.N.; Mendes, A.P.S.; Araújo, S.C.; França, L.C.S.; Franco, E.C.S.; Leal, W.G.; da Silva, A.B.F. Density Functional Theory (DFT) Study of Edaravone Derivatives as Antioxidants. Int. J. Mol. Sci. 2012, 13, 7594-7606.

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