Computational study of substituent effects on the physicochemical properties and chemical reactivity of selected antiparasitic 5-nitrofurans
Por:
Barrientos-Salcedo C., Espinoza B., Soriano-Correa C.
Publicada:
5 dic 2018
Resumen:
American Trypanosomiasis is a disease caused by the protozoan parasite
Trypanosoma cruzi agent. Nifurtimox and benznidazole are effective drugs
in the acute phase; however, are toxic and have adverse effects.
Nonetheless, the nitroheterocycles are good models to design other
compounds with less side effects. Theoretical and experimental studies
have been performed about the structure and mode action of these drugs
and at present, no effective treatment of this disease has been
established yet, and the parasitic infections increase each year. The
aim of this work, was to analyze the substituent effects on the
physicochemical properties and chemical reactivity of selected
antiparasitic 5-nitrofurans, using quantum-chemical descriptors:
acidity, proton affinities, SESE, potential ionization, hardness,
electrophilicity, aromaticity, dipole moment and Fukui functions at the
OFT-M06-2X level in aqueous solution. The acidity of the azomethine
group increases with the presence of the electron-withdrawing groups.
The electron-donating groups favor the basicity and the energy of
stabilization in the active molecule (NFX). The atomic charges, the
quantum chemical descriptors and Fukui function (f(k)(+)) showed that
the main reactivity takes place on the Ar-NO2. These results reinforce
the importance of the nitro group in the redox processes of the
5-nitrofurans that are involved in the trypanocidal effect. (C) 2018
Elsevier B.V. All rights reserved.
Filiaciones:
Barrientos-Salcedo C.:
Univ Veracruzana, Fac Bioanal, Lab Quim Med & Quimiogenom, Campus Veracruz Boca del Rio, Boca Del Rio 91700, Veracruz, Mexico
Laboratorio de Química Médica y Quimiogenómica, Facultad de Bioanálisis Campus Veracruz - Boca del Río, Universidad Veracruzana, Veracruz, 91700, Mexico
Espinoza B.:
UNAM, Inst Invest Biomed, Dept Inmunol, Nueva Sede, Ciudad De Mexico 04510, Mexico
Departamento de Inmunología, Instituto de Investigaciones Biomédicas, UNAM, Nueva Sede. Circuitos Campos Deportivos, CU, Ciudad de México, 04510, Mexico
Soriano-Correa C.:
Univ Nacl Autonoma Mexico, Fac Estudios Super Zaragoza, Quim Computac, CP 09230, Ciudad De Mexico 09230, Mexico
Química Computacional, Facultad de Estudios Superiores -Zaragoza, Universidad Nacional Autónoma de México (UNAM), Iztapalapa, Ciudad de México, 09230, Mexico
|