Structure-activity relations of azafluorenone and azaanthraquinone as antimicrobial compounds.
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.
Koyama
Junko
J
Faculty of Pharmaceutical Sciences, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan. j-koyama@kobrpharma-u.ac.jp
Morita
Izumi
I
Kobayashi
Norihiro
N
Osakai
Toshiyuki
T
Usuki
Yoshinosuke
Y
Taniguchi
Makoto
M
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001372:Aza Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D004563:Electrochemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001372:Aza Compounds; D005449:Fluorenes