title: 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.
authors.affiliation: Departamento de Química, ICE, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Bianca da S
authors.initials: BDS
authors.lastname: Ferreira
authors.affiliation: Departamento de Química, ICE, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Angelina M
authors.initials: AM
authors.lastname: de Almeida
authors.affiliation: Departamento de Parasitologia, Microbiologia e Imunologia, ICB, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Thiago C
authors.initials: TC
authors.lastname: Nascimento
authors.affiliation: Departamento de Parasitologia, Microbiologia e Imunologia, ICB, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Pedro P
authors.initials: PP
authors.lastname: de Castro
authors.affiliation: Departamento de Parasitologia, Microbiologia e Imunologia, ICB, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Vania L
authors.initials: VL
authors.lastname: Silva
authors.affiliation: Departamento de Parasitologia, Microbiologia e Imunologia, ICB, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Claúdio G
authors.initials: CG
authors.lastname: Diniz
authors.affiliation: Departamento de Química, ICE, Universidade Federal de Juiz de Fora, 36036-330 Juiz de Fora, MG, Brazil.
authors.forename: Mireille
authors.initials: M
authors.lastname: Le Hyaric
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects*; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003959:Diamines
keywords: Antibacterial; Antifungal; Lipophilicity; MRSA; N-Acyldiamines