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  • Title: Synthesis and biological evaluation of a new series of N-acyldiamines as potential antibacterial and antifungal agents.
    Author: Ferreira BDS, de Almeida AM, Nascimento TC, de Castro PP, Silva VL, Diniz CG, Le Hyaric M.
    Journal: Bioorg Med Chem Lett; 2014 Oct 01; 24(19):4626-4629. PubMed ID: 25219900.
    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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