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Molecules 2016, 21(12), 1716; doi:10.3390/molecules21121716

Synthesis, Antifungal Evaluation and In Silico Study of N-(4-Halobenzyl)amides

Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, 58051-900 João Pessoa-PB, Brazil
Departamento de Química, Universidade Federal da Paraíba, 58051-900 João Pessoa-PB, Brazil
Author to whom correspondence should be addressed.
Academic Editor: Diego Muñoz-Torrero
Received: 28 October 2016 / Revised: 8 December 2016 / Accepted: 9 December 2016 / Published: 13 December 2016
(This article belongs to the Section Medicinal Chemistry)
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A collection of 32 structurally related N-(4-halobenzyl)amides were synthesized from cinnamic and benzoic acids through coupling reactions with 4-halobenzylamines, using (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as a coupling agent. The compounds were identified by spectroscopic methods such as infrared, 1H- and 13C- Nuclear Magnetic Resonance (NMR) and high-resolution mass spectrometry. The compounds were then submitted to antimicrobial tests by the minimum inhibitory concentration method (MIC) and nystatin was used as a control in the antifungal assays. The purpose of the tests was to evaluate the influence of structural changes in the cinnamic and benzoic acid substructures on the inhibitory activity against strains of Candida albicans, Candida tropicalis, and Candida krusei. A quantitative structure-activity relationship (QSAR) study with KNIME v. 3.1.0 and Volsurf v. 1.0.7 softwares were realized, showing that descriptors DRDRDR, DRDRAC, L4LgS, IW4 and DD2 influence the antifungal activity of the haloamides. In general, 10 benzamides revealed fungal sensitivity, especially a vanillic amide which enjoyed the lowest MIC. The results demonstrate that a hydroxyl group in the para position, and a methoxyl at the meta position enhance antifungal activity for the amide skeletal structure. In addition, the double bond as a spacer group appears to be important for the activity of amide structures. View Full-Text
Keywords: halogenated amides; antimicrobial activity; Candida; vanillic acid derivatives halogenated amides; antimicrobial activity; Candida; vanillic acid derivatives

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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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MDPI and ACS Style

Montes, R.C.; Perez, A.L.A.L.; Medeiros, C.I.S.; Araújo, M.O.; Lima, E.O.; Scotti, M.T.; Sousa, D.P. Synthesis, Antifungal Evaluation and In Silico Study of N-(4-Halobenzyl)amides. Molecules 2016, 21, 1716.

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