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Amides Derived from Vanillic Acid: Coupling Reactions, Antimicrobial Evaluation, and Molecular Docking
Joint Authors
Pessôa, Hilzeth L. F.
Santos Oliveira, Ana Júlia de Morais
de Castro, Ricardo Dias
Wadood, Abdul
de Sousa, Damião Pergentino
Source
Issue
Vol. 2019, Issue 2019 (31 Dec. 2019), pp.1-11, 11 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2019-04-15
Country of Publication
Egypt
No. of Pages
11
Main Subjects
Abstract EN
A series of amides derived from vanillic acid were obtained by coupling reactions using PyBOP ((Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) and DCC (Dicyclohexylcarbodiimide) coupling reagents.
These were submitted to biological evaluation for species of Candida, Staphylococcus, and Pseudomonas.
The microdilution method in broth was used for the antimicrobial testing to determine the Minimum Inhibitory Concentration (MIC) and to verify the likely mechanism of action for antifungal activity.
The ten amides were obtained with yields ranging from 28.81 to 86.44%, and three compounds were novel.
In the antibacterial evaluation, the amides (in their greatest concentrations) were bioactive against Staphylococcus aureus strain ATCC 25925.
Meanwhile, all of the tested amides presented antifungal activity against at least one strain.
The amide with best antifungal profile was compound 7, which featured an MIC of 0.46 μmol/mL, and a mechanism of action involving the plasma membrane and fungal cell wall.
The presence of a methyl group in the para position of the aromatic ring is suggested which enhances the activity of the compound against fungi.
Docking studies of the ten compounds using the protein 14α-demethylase as a biological target were also performed.
The biological results presented good correlation with molecular docking studies demonstrating that a possible site of antifungal action for bioactive amides is the enzyme 14α-demethylase.
American Psychological Association (APA)
Santos Oliveira, Ana Júlia de Morais& de Castro, Ricardo Dias& Pessôa, Hilzeth L. F.& Wadood, Abdul& de Sousa, Damião Pergentino. 2019. Amides Derived from Vanillic Acid: Coupling Reactions, Antimicrobial Evaluation, and Molecular Docking. BioMed Research International،Vol. 2019, no. 2019, pp.1-11.
https://search.emarefa.net/detail/BIM-1128388
Modern Language Association (MLA)
Santos Oliveira, Ana Júlia de Morais…[et al.]. Amides Derived from Vanillic Acid: Coupling Reactions, Antimicrobial Evaluation, and Molecular Docking. BioMed Research International No. 2019 (2019), pp.1-11.
https://search.emarefa.net/detail/BIM-1128388
American Medical Association (AMA)
Santos Oliveira, Ana Júlia de Morais& de Castro, Ricardo Dias& Pessôa, Hilzeth L. F.& Wadood, Abdul& de Sousa, Damião Pergentino. Amides Derived from Vanillic Acid: Coupling Reactions, Antimicrobial Evaluation, and Molecular Docking. BioMed Research International. 2019. Vol. 2019, no. 2019, pp.1-11.
https://search.emarefa.net/detail/BIM-1128388
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1128388