Antimycobacterial and antifungal isosters of salicylamides.
A set of 40 derivatives of 3-hydroxypicolinic acid and 2-sulfanylbenzoic acid, isosteric to salicylanilides was synthesized. The compounds were evaluated for in vitro activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium, Candida albicans, Candida tropicalis, Candida krusei, Candida glabrata, Trichosporon beigelii, Aspergillus fumigatus, Absidia corymbifera, Trichophyton mentagrophytes and Microsporum gypseum. Structure-activity relationships of antimycobacterial activity and antifungal activity against T. mentagrophytes and M. gypseum were analyzed by the Free-Wilson method. An increase in antimycobacterial activity was observed only for the sulfanylbenzoic acid derivatives, especially those with the benzyl moiety. The antifungal activity was not significant.
Waisser
Karel
K
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic. waisser@faf.cuni.cz
Pesina
Milan
M
Holý
Pavel
P
Pour
Milan
M
Bures
Otakar
O
Kunes
Jisí
J
Klimesová
Vsra
V
Buchta
Vladimír
V
Kubanová
Petra
P
Kaustová
Jarmila
J
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019817:Benzoic Acid / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D010848:Picolinic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012458:Salicylanilides / Q000737:chemistry*; D012459:Salicylates; D013329:Structure-Activity Relationship; D013425:Sulfanilic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013438:Sulfhydryl Compounds
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D001565:Benzoates; D010848:Picolinic Acids; D012458:Salicylanilides; D012459:Salicylates; D013425:Sulfanilic Acids; D013438:Sulfhydryl Compounds; C049246:3-hydroxypicolinic acid; D019817:Benzoic Acid; C441201:thiosalicylic acid