Synthesis and evaluation of N-alkyl-9-aminoacridines with antibacterial activity.

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Bioorganic & medicinal chemistry letters, ISSN: 1464-3405, Vol: 24, Issue: 14, Page: 3014-7

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Benoit, Adam R; Schiaffo, Charles; Salomon, Christine E; Goodell, John R; Hiasa, Hiroshi; Ferguson, David M
Elsevier BV
Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Chemistry
article description
A series of 9-alkylaminoacridines were synthesized and evaluated for activity against two strains of methicillin-resistant and one strain of methicillin-sensitive Staphylococcus aureus. Results are presented that show a clear structure activity relationship between the N-alkyl chain length and antibacterial activity with peak MIC99 values of 2-3 μM for alkyl chains ranging from 10 to 14 carbons in length. Although prior work has linked the function of acridine-based compounds to intercalation and topoisomerase inhibition, the present results show that 9-alkylaminoacridines likely function as amphiphilic membrane-active disruptors potentially in a similar manner as quaternary ammonium antimicrobials.