(2-Arylhydrazonomethyl)-substituted xanthones as antimycotics: synthesis and fungistatic activity against Candida species.
A series of arylhydrazones derived from various 6,8-diacetoxy- or 6,8-dihydroxy-9-oxo-9H-xanthene carboxaldehydes were synthesized and evaluated for their in vitro antifungal properties against two human pathogenic yeasts (Candida albicans and C. krusei) according to a diffusion method. The activity was strongly dependent from the position of the (1-arylhydrazinyl-2-ylidene)methyl chain in the xanthone molecular skeleton. Compounds having the nitrogen side chain in the 4-position, with a further halogen substitution on the terminal phenyl ring showed fungistatic effects. Within this series, the 4-fluorophenylhydrazinyl derivative 13g exhibited the highest activity, particularly against C. krusei, with a greater efficacy than that of econazole, used as reference.
Moreau
Stéphane
S
Groupe d'Etude des Substances Naturelles d'Intérêt Thérapeutique (GESNIT, EA 491), Université Victor-Segalen Bordeaux 2, 146 rue Léo-Saignat, F-33076 Bordeaux cedex, France.
Varache-Lembège
Martine
M
Larrouture
Stéphane
S
Fall
Djibril
D
Neveu
Arlette
A
Deffieux
Gérard
G
Vercauteren
Joseph
J
Nuhrich
Alain
A
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D044004:Xanthones
D000935:Antifungal Agents; D014966:Xanthenes; D044004:Xanthones; C009689:xanthone