Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives

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 mo...

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Bibliographic Details
Published in:Chemical biology & drug design 2015-09, Vol.86 (3), p.344-350
Main Authors: Rezende Jr, 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.
Format: Article
Language:English
Subjects:
Alkylation
Amides - chemical synthesis
Amides - pharmacology
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
antibacterial
diamines
Diamines - chemical synthesis
Diamines - pharmacology
Gram-Negative Bacteria - drug effects
Gram-Positive Bacteria - drug effects
lipophilicity
Microbial Sensitivity Tests
quinic acid
Quinic Acid - analogs & derivatives
Quinic Acid - chemical synthesis
Quinic Acid - chemistry
Quinic Acid - pharmacology
Structure-Activity Relationship
Surface-Active Agents - pharmacology
tuberculosis
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Summary: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. Synthesis of amphiphilic amides of quinic acid derivatives. Evaluation of antibacterial properties against Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa and Mycobacterium tuberculosis. Structure activity relationship of the synthesized compounds.
ISSN:1747-0277
1747-0285
DOI:10.1111/cbdd.12498