Synthesis and biological evaluation of a new series of N-acyldiamines as potential antibacterial and antifungal agents
Abstract
In continuation of our efforts to find new antimicrobial compounds, series of fatty N-acyldiamines were prepared from fatty methyl esters and 1,2-ethylenediamine, 1,3-propanediamine or 1,4-butanediamine. The synthesized compounds were screened for their antibacterial activity against Gram-positive bacteria (Staphylococcus aureus, Staphylococcus epidermidis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and for their antifungal activity against four species of Candida (C. albicans, C. tropicalis, C. glabrata and C. parapsilosis). Compounds 5a (N-(2-aminoethyl)dodecanamide), 5b (N-(2-aminoethyl)tetracanamide) and 6d (N-(3-aminopropyl)oleamide) were the most active against Gram-positive bacteria, with MIC values ranging from 1 to 16μg/mL and were evaluated for their activity against 21 clinical isolates of methicillin-resistant S. aureus. All the compounds exhibited good to moderate antifungal activity. Compared to chloramphenicol, compound 6b displayed a similar activity (MIC50=16μg/mL). A positive correlation could be established between lipophilicity and biological activity.
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A series of fatty N-acyldiamines demonstrated moderate to good antifungal activity against C. albicans, C. tropicalis, C. glabrata, and C. parapsilosis.
“A series of fatty N-acyldiamines, prepared from fatty methyl esters and 1,2-ethylenediamine, 1,3-propanediamine, or 1,4-butanediamine, have also demonstrated moderate to good antifungal activity against C. albicans, C. tropicalis, C. glabrata, and C. parapsilosis [266].”
From Candida glabrata Biofilms: How Far Have We Come? (2017) · cites this paper as [266]
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- Authors
- Ferreira, B. D. S., de Almeida, A. M., Nascimento, T. C., de Castro, P. P., Silva, V. L., Diniz, C. G., & Le Hyaric, M.
- Affiliations
- Universidade Federal de Juiz de Fora (BR)
- Venue
- Bioorganic & Medicinal Chemistry Letters
- Publisher
- Elsevier BV
- Published
- 2014-10
- Volume
- 24
- Issue
- 19
- Pages
- 4626-4629
- ISSN
- 0960-894X (ISSN-L)
- OpenAlex
- W2089801154
- Cited by
- 14
- References
- 13
- Citations by year
- 2025: 2 · 2024: 2 · 2021: 2 · 2020: 2 · 2019: 1 · 2018: 2 · 2017: 2 · 2016: 1
- FWCI
- 0.44
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Bioorganic & Medicinal Chemistry Letters (publishedVersion)
- PubMed (publishedVersion)
- Funders
- CAPES
- CNPq
- FAPEMIG
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Biological Evaluation
- Physical Sciences › Chemistry › Organic Chemistry › Antimicrobial agents and applications
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Characterization of Heterocyclic Compounds
- Keywords
- antibacterial agents, antifungal agents, ethane-1,2-diamine, 1,3-propanediamine, 1,4-butanediamine, Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Candida albicans, Candida tropicalis, Candida glabrata, Candida parapsilosis, Escherichia coli, Pseudomonas aeruginosa, minimum inhibitory concentration, lipophilicity, structure-activity relationship
- MeSH terms
- Anti-Bacterial Agents, Antifungal Agents, Candida, Diamines, Dose-Response Relationship, Drug, Gram-Negative Bacteria, Gram-Positive Bacteria, Microbial Sensitivity Tests, Structure-Activity Relationship, Molecular Structure
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