Next Article in Journal
Functional Analysis of the Fusarielin Biosynthetic Gene Cluster
Previous Article in Journal
Plasma Processing with Fluorine Chemistry for Modification of Surfaces Wettability
Article Menu
Issue 12 (December) cover image

Export Article

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

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

1
Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, 58051-900 João Pessoa-PB, Brazil
2
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)
View Full-Text   |   Download PDF [1715 KB, uploaded 13 December 2016]   |  

Abstract

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
Figures

Figure 1

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).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top