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Molecules 2018, 23(9), 2129; https://doi.org/10.3390/molecules23092129

One-Electron Reduction Potentials: Calibration of Theoretical Protocols for Morita–Baylis–Hillman Nitroaromatic Compounds in Aprotic Media

Chemistry Department, Federal University of Paraiba, João Pessoa 58051-900, Brazil
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Received: 30 July 2018 / Revised: 9 August 2018 / Accepted: 11 August 2018 / Published: 24 August 2018
(This article belongs to the Special Issue Theoretical Investigations of Reaction Mechanisms)
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Abstract

Nitroaromatic compounds—adducts of Morita–Baylis–Hillman (MBHA) reaction—have been applied in the treatment of malaria, leishmaniasis, and Chagas disease. The biological activity of these compounds is directly related to chemical reactivity in the environment, chemical structure of the compound, and reduction of the nitro group. Because of the last aspect, electrochemical methods are used to simulate the pharmacological activity of nitroaromatic compounds. In particular, previous studies have shown a correlation between the one-electron reduction potentials in aprotic medium (estimated by cyclic voltammetry) and antileishmanial activities (measured by the IC50) for a series of twelve MBHA. In the present work, two different computational protocols were calibrated to simulate the reduction potentials for this series of molecules with the aim of supporting the molecular modeling of new pharmacological compounds from the prediction of their reduction potentials. The results showed that it was possible to predict the experimental reduction potential for the calibration set with mean absolute errors of less than 25 mV (about 0.6 kcal·mol−1). View Full-Text
Keywords: Morita–Baylis–Hilman Adducts; biological activity; reduction potentials; medicinal chemistry Morita–Baylis–Hilman Adducts; biological activity; reduction potentials; medicinal chemistry
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Francisco da Silva, A.; João da Silva Filho, A.; Vasconcellos, M.L.A.A.; Luís de Santana, O. One-Electron Reduction Potentials: Calibration of Theoretical Protocols for Morita–Baylis–Hillman Nitroaromatic Compounds in Aprotic Media. Molecules 2018, 23, 2129.

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