title: Synthesis and antimicrobial activity of novel amphiphilic aromatic amino alcohols.
abstract: We report in this work the preparation and in vitro antimicrobial evaluation of novel amphiphilic aromatic amino alcohols synthesized by reductive amination of 4-alkyloxybenzaldehyde with 2-amino-2-hydroxymethyl-propane-1,3-diol. The antibacterial activity was determined against four standard strains (Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeruginosa) and 21 clinical isolates of methicillin-resistant Staphylococcus aureus. The antifungal activity was evaluated against four yeast (Candida albicans, Candida tropicalis, Candida glabrata and Candida parapsilosis). The results obtained showed a strong positive correlation between the lipophilicity and the antibiotic activity of the tested compounds. The best activities were obtained against the Gram-positive bacteria (MIC=2-16μgml(-1)) for the five compounds bearing longer alkyl chains (4c-g; 8-14 carbons), which were also the most active against Candida (MIC=2-64μgml(-1)). Compound 4e exhibited the highest levels of inhibitory activity (MIC=2-16μgml(-1)) against clinical isolates of MRSA. A concentration of twice the MIC resulted in bactericidal activity of 4d against 19 of the 21 clinical isolates.
authors.affiliation: Departamento de Qumica, 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.forename: Thiago
authors.initials: T
authors.lastname: Nascimento
authors.forename: Bianca S
authors.initials: BS
authors.lastname: Ferreira
authors.forename: Pedro P
authors.initials: PP
authors.lastname: de Castro
authors.forename: Vânia L
authors.initials: VL
authors.lastname: Silva
authors.forename: Claúdio G
authors.initials: CG
authors.lastname: Diniz
authors.forename: Mireille
authors.initials: M
authors.lastname: Le Hyaric
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D005658:Fungi / Q000187:drug effects*; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000605:Amino Alcohols; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D013501:Surface-Active Agents