Synthesis and Antibacterial Activity of Alkylated Diamines and Amphiphilic Amides of Quinic Acid Derivatives. (20th January 2015)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Chemical biology & drug design. Volume 86:Number 3(2015:Sep.)
• Page Start: 344
• Page End: 350
• Publication Date: 2015-01-20
• Subjects: Drugs -- Design -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; 615.19005
• DOI: 10.1111/cbdd.12498
• Languages: English
• ISSNs: 1747-0277

Abstract

<abstract abstract-type="main" id="cbdd12498-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p>Different series of <italic>N</italic>‐alkylated diamines and their derivatives condensed to quinic acid were synthesized and tested for antibacterial properties against <italic>Staphylococcus aureus</italic>, <italic> Staphylococcus epidermidis</italic>, <italic> Pseudomonas aeruginosa, </italic> and <italic>Mycobacterium tuberculosis</italic>. 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 <bold>2a‐h</bold> displayed an activity similar to that of ethambutol against <italic>Mycobacterium tuberculosis</italic>.</p> </abstract>