Library synthesis and antibacterial investigation of cationic anthraquinone analogs.

Abstract:

: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.

journal_name

ACS Comb Sci

authors

Fosso MY,Chan KY,Gregory R,Chang CW

doi

10.1021/co2002075

subject

Has Abstract

pub_date

2012-03-12 00:00:00

pages

231-5

issue

3

eissn

2156-8952

issn

2156-8944

journal_volume

14

pub_type

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