Library synthesis and antibacterial investigation of cationic anthraquinone analogs.
We report the parallel synthesis of a series of novel 4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d][1,2,3]triazol-3-ium chloride salts, which are analogs to cationic anthraquinones. Three synthetic protocols were examined leading to a convenient and facile library synthesis of the cationic anthraquinone analogs that contain double alkyl chains of various lengths (C(2)-C(12)) at N-1 and N-3 positions. The antibacterial activities of these compounds were evaluated against Gram-positive bacterium Staphylococcus aureus and Gram-negative bacterium Escherichia coli. The antibacterial activities of these compounds were expected to be associated with the structural features of naphthoquinone, cation and lypophilic alkyl chain and, interestingly, they showed much higher levels of antibacterial activities against G+ than G- bacteria. In addition, when the total number of carbon atoms of the alkyl groups at both N-1 and N-3 positions lies between 9 and 18, the bactericidal activity against S. aureus increased with increasing alkyl chain length at both N-atoms with MIC ≤ 1 μg/mL.
Department of Chemistry and Biochemistry, Utah State University, Logan, 84322-0300, United States.
Marina Y
MY
Fosso
Ka Yee
KY
Chan
Rylee
R
Gregory
Cheng-Wei Tom
CW
Chang
D000478:Alkylation; D000880:Anthraquinones / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002412:Cations; D003500:Cyclization; D004926:Escherichia coli / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects*
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D002412:Cations; D054852:Small Molecule Libraries