Structure–activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds

Antimicrobial activities of azafluorenones, 1-azaanthraquinones, and 2-azaanthraquinones were tested. Antimicrobial activities of two azafluorenones, four 1-azaanthraquinones, five 2-azaanthraquinones, and one 2-azaquinone were tested. Several azaanthraquinones possessed broad, potent activity, whil...

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Published inBioorganic & medicinal chemistry letters Vol. 15; no. 4; pp. 1079 - 1082
Main Authors Koyama, Junko, Morita, Izumi, Kobayashi, Norihiro, Osakai, Toshiyuki, Usuki, Yoshinosuke, Taniguchi, Makoto
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 15.02.2005
Elsevier
Subjects
Anthraquinones - chemical synthesis
Anthraquinones - pharmacology
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal Agents - chemical synthesis
Antifungal Agents - pharmacology
Aza Compounds - chemical synthesis
Aza Compounds - pharmacology
Biological and medical sciences
Electrochemistry
Fluorenes - chemical synthesis
Fluorenes - pharmacology
General aspects
Hydrogen-Ion Concentration
Medical sciences
Microbial Sensitivity Tests
Oxidation-Reduction
Pharmacology. Drug treatments
Structure-Activity Relationship
Electrochemical properties
Structure activity relation
Nitrogen heterocycle
Quinone
Aromatic compound
Reduction potential
Property structure relationship
Tricyclic compound
Chemical synthesis
In vitro
Antimicrobial agent
Lipophilicity
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Summary:Antimicrobial activities of azafluorenones, 1-azaanthraquinones, and 2-azaanthraquinones were tested. Antimicrobial activities of two azafluorenones, four 1-azaanthraquinones, five 2-azaanthraquinones, and one 2-azaquinone were tested. Several azaanthraquinones possessed broad, potent activity, while the azafluorenones demonstrated weak activity. The following structure–activity relationship was postulated: (1) activity decreased in the order 2-azaanthraquinones > 1-azaanthraquinones > azafluorenones; and (2) a hydroxyl group at the peri-carbonyl group enhanced activity. In addition, correlations among reduction potential, hydrophobic parameter, and antimicrobial activity were discussed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2004.12.059