Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)- 1-phenylethanol derivatives

Daniela De Vita, Luigi Scipione, Silvano Tortorella, Paolo Mellini, Barbara Di Rienzo, Giovanna Simonetti, Felicia Diodata D'Auria, Simona Panella, Roberto Cirilli, Roberto Di Santo, Anna Teresa Palamara

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)334-342
Number of pages9
JournalEuropean Journal of Medicinal Chemistry
Volume49
DOIs
Publication statusPublished - Mar 2012

Keywords

  • Antifungal imidazoles
  • Candida albicans species
  • Enantiomers separation
  • Human monocytic cell line
  • Non-albicans Candida species

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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  • Cite this

    De Vita, D., Scipione, L., Tortorella, S., Mellini, P., Di Rienzo, B., Simonetti, G., D'Auria, F. D., Panella, S., Cirilli, R., Di Santo, R., & Palamara, A. T. (2012). Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)- 1-phenylethanol derivatives. European Journal of Medicinal Chemistry, 49, 334-342. https://doi.org/10.1016/j.ejmech.2012.01.034