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Molecules 2018, 23(3), 599; https://doi.org/10.3390/molecules23030599

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines

1
Departamento de Química Orgánica-Laboratorio de Síntesis de Fármacos Heterocíclicos, Escuela Nacional de Ciencias Biológicas-IPN, Prolongación de Carpio y Plan de Ayala S/N, Colonia Santo Tomás, C.P. 11340 Ciudad de México, Mexico
2
Departamento de Microbiología-Laboratorio de Biología Molecular de Bacterias y Levaduras, Escuela Nacional de Ciencias Biológicas-IPN, Prolongación de Carpio y Plan de Ayala S/N, Colonia Santo Tomás, C.P. 11340 Ciudad de México, Mexico
3
Instituto de Química-UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán, C.P. 04510 Ciudad de México, Mexico
4
Departamento de Bioquímica-Laboratorio de Biotecnología y Bioinformática Genómica, Escuela Nacional de Ciencias Biológicas-IPN, Prolongación de Carpio y Plan de Ayala S/N, Colonia Santo Tomás, C.P. 11340 Ciudad de México, Mexico
*
Authors to whom correspondence should be addressed.
Received: 7 February 2018 / Revised: 2 March 2018 / Accepted: 5 March 2018 / Published: 7 March 2018
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of 3-benzoyl imidazo[1,2-a]pyrimidines, obtained from N-heteroarylformamidines in good yields, was tested in silico and in vitro for binding and inhibition of seven Candida species (Candida albicans (ATCC 10231), Candida dubliniensis (CD36), Candida glabrata (CBS138), Candida guilliermondii (ATCC 6260), Candida kefyr, Candida krusei (ATCC 6358) and Candida tropicalis (MYA-3404)). To predict binding mode and energy, each compound was docked in the active site of the lanosterol 14α-demethylase enzyme (CYP51), essential for fungal growth of Candida species. Antimycotic activity was evaluated as the 50% minimum inhibitory concentration (MIC50) for the test compounds and two reference drugs, ketoconazole and fluconazole. All test compounds had a better binding energy (range: −6.11 to −9.43 kcal/mol) than that found for the reference drugs (range: 48.93 to −6.16 kcal/mol). In general, the test compounds showed greater inhibitory activity of yeast growth than the reference drugs. Compounds 4j and 4f were the most active, indicating an important role in biological activity for the benzene ring with electron-withdrawing substituents. These compounds show the best MIC50 against C. guilliermondii and C. glabrata, respectively. The current findings suggest that the 3-benzoyl imidazo[1,2-a]pyrimidine derivatives, herein synthesized by an accessible methodology, are potential antifungal drugs. View Full-Text
Keywords: 3-benzoyl imidazo[1,2-a]pyrimidines; molecular docking; antimycotic activity; Lanosterol 14α-demethylase; Candida spp. 3-benzoyl imidazo[1,2-a]pyrimidines; molecular docking; antimycotic activity; Lanosterol 14α-demethylase; Candida spp.
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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. (CC BY 4.0).

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Gómez-García, O.; Andrade-Pavón, D.; Campos-Aldrete, E.; Ballinas-Indilí, R.; Méndez-Tenorio, A.; Villa-Tanaca, L.; Álvarez-Toledano, C. Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines. Molecules 2018, 23, 599.

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