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. © 2012 Elsevier Masson SAS. All rights reserved.
Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives / DE VITA, Daniela; Scipione, Luigi; Tortorella, Silvano; Mellini, Paolo; DI RIENZO, Barbara; Simonetti, Giovanna; D'Auria, Felicia Diodata; Panella, Simona; Roberto, Cirilli; DI SANTO, Roberto; Palamara, ANNA TERESA. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - STAMPA. - 49:(2012), pp. 334-342. [10.1016/j.ejmech.2012.01.034]
Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives
DE VITA, DANIELA;SCIPIONE, Luigi;TORTORELLA, Silvano;MELLINI, PAOLO;DI RIENZO, Barbara;SIMONETTI, Giovanna;D'AURIA, Felicia Diodata;PANELLA, SIMONA;DI SANTO, Roberto;PALAMARA, ANNA TERESA
2012
Abstract
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. © 2012 Elsevier Masson SAS. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.