title: Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives.
abstract: Different series of N-alkylated diamines and their derivatives condensed to quinic acid were synthesized and tested for antibacterial properties against Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, and Mycobacterium tuberculosis. The lipophilic chain and carbohydrate moiety modulate the antibacterial activity and the compounds showed a structure-activity relationship. Overall, 11 compounds displayed better activity than chloramphenicol against Gram-positive and Gram-negative bacteria. Monoalkylated amines 2a-h displayed an activity similar to that of ethambutol against Mycobacterium tuberculosis.
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Celso O
authors.initials: CO
authors.lastname: Rezende
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Larissa A
authors.initials: LA
authors.lastname: Oliveira
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Bruno A
authors.initials: BA
authors.lastname: Oliveira
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Camila G
authors.initials: CG
authors.lastname: Almeida
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Bianca S
authors.initials: BS
authors.lastname: Ferreira
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Mireille
authors.initials: M
authors.lastname: Le Hyaric
authors.affiliation: Instituto Nacional de Infectologia Evandro Chagas-Fiocruz, 21040-360, Rio de Janeiro, RJ, Brazil.
authors.forename: Guilherme S L
authors.initials: GS
authors.lastname: Carvalho
authors.affiliation: Instituto Nacional de Infectologia Evandro Chagas-Fiocruz, 21040-360, Rio de Janeiro, RJ, Brazil.
authors.forename: Maria Cristina S
authors.initials: MC
authors.lastname: Lourenço
authors.affiliation: Instituto Carlos Chagas-Fiocruz, 81350-010, Curitiba, PR, Brazil.
authors.forename: Michel
authors.initials: M
authors.lastname: Batista
authors.affiliation: Instituto Carlos Chagas-Fiocruz, 81350-010, Curitiba, PR, Brazil.
authors.forename: Fabricio K
authors.initials: FK
authors.lastname: Marchini
authors.affiliation: Departamento de Parasitologia, Microbiologia e Imunologia, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Vânia L
authors.initials: VL
authors.lastname: Silva
authors.affiliation: Departamento de Parasitologia, Microbiologia e Imunologia, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Claudio G
authors.initials: CG
authors.lastname: Diniz
authors.affiliation: Departamento de Química, Universidade Federal de Juiz de Fora, 36036-330, Juiz de Fora, MG, Brazil.
authors.forename: Mauro V
authors.initials: MV
authors.lastname: Almeida
mesh_terms: D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D003959:Diamines / Q000138:chemical synthesis* / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000494:pharmacology
chemical_list: D000577:Amides; D000900:Anti-Bacterial Agents; D003959:Diamines; D013501:Surface-Active Agents; D011801:Quinic Acid
keywords: antibacterial; diamines; lipophilicity; quinic acid; tuberculosis