Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives.
A new series of aromatic ester and carbamate derivatives of 2-(1H-imidazol-1-yl)-1-phenylethanol were synthesized and evaluated for their antifungal activity towards Candida albicans and non-albicans Candida species strains. The aromatic biphenyl ester derivatives 6a-c were more active than the reference compound fluconazole. 6c possesses a MIC mean values of 1.7 ± 1.4 μg mL(-1)vs C. albicans and 1.9 ± 2.0 μg mL(-1)vs non-albicans Candida species strains. The racemic mixtures of 6a, b were purified to afford the pure enantiomers. The (-) isomers were up to 500 times more active than (+) isomers. (-)-6a and (-)-6b were thirty and ninety times more active than fluconazole towards C. krusei strain respectively. The racemates of 6a-c showed low cytotoxicity against human monocytic cell line (U937) with 6a demonstrating a CC(50) greater than 128 μg mL(-1).
Istituto Pasteur-Fondazione Cenci Bolognetti, Dipartimento di Chimica e Tecnologie del Farmaco Sapienza Università di Roma, Roma, Italy.
Daniela
D
De Vita
Luigi
L
Scipione
Silvano
S
Tortorella
Paolo
P
Mellini
Barbara
B
Di Rienzo
Giovanna
G
Simonetti
Felicia Diodata
FD
D'Auria
Simona
S
Panella
Roberto
R
Cirilli
Roberto
R
Di Santo
Anna Teresa
AT
Palamara
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects*; D002176:Candida albicans / Q000187:drug effects; D002177:Candidiasis / Q000188:drug therapy; D002460:Cell Line; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010626:Phenylethyl Alcohol / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D000935:Antifungal Agents; D007093:Imidazoles; D010626:Phenylethyl Alcohol