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Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives
Author(s) -
Rezende Celso O.,
Oliveira Larissa A.,
Oliveira Bruno A.,
Almeida Camila G.,
Ferreira Bianca S.,
Le Hyaric Mireille,
Carvalho Guilherme S. L.,
Lourenço Maria Cristina S.,
Batista Michel,
Marchini Fabricio K.,
Silva Vânia L.,
Diniz Claudio G.,
Almeida Mauro V.
Publication year - 2015
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12498
Subject(s) - antibacterial activity , chemistry , quinic acid , staphylococcus epidermidis , mycobacterium tuberculosis , alkylation , bacteria , staphylococcus aureus , antibacterial agent , moiety , organic chemistry , stereochemistry , biochemistry , antibiotics , biology , tuberculosis , catalysis , medicine , genetics , pathology
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 .