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Citation
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HERO ID
7416314
Reference Type
Journal Article
Title
Synthesis and antifungal activity of a new series of 2-(1H-imidazol-1-yl)-1-phenylethanol derivatives
Author(s)
De Vita, D; Scipione, L; Tortorella, S; Mellini, P; Di Rienzo, B; Simonetti, G; D'Auria, FD; Panella, S; Cirilli, R; Di Santo, R; Palamara, AT; ,
Year
2012
Is Peer Reviewed?
Yes
Journal
European Journal of Medicinal Chemistry
ISSN:
0223-5234
EISSN:
1768-3254
Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
Location
PARIS
Volume
49
Page Numbers
334-342
Language
English
PMID
22321993
DOI
10.1016/j.ejmech.2012.01.034
Web of Science Id
WOS:000302033300033
URL
https://linkinghub.elsevier.com/retrieve/pii/S0223523412000499
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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).
Keywords
Antifungal imidazoles; Candida albicans species; Enantiomers separation; Human monocytic cell line; Non-albicans Candida species; 1 (4 chlorophenyl) 2 (1h imidazol 1 yl)ethyl (2,6 dichloropyridin 4 yl)carbamate; 1 (4 chlorophenyl) 2 (1h imidazol 1 yl)ethyl 3 (trifluoromethyl)benzoate; 1 (4 chlorophenyl) 2 (1h imidazol 1 yl)ethyl [(4 propan 2 yl)phenyl]carbamate; 1 (4 chlorophenyl) 2 (1h imidazol 1 yl)ethyl biphenyl 4 carboxylate; 1 (4 chlorophenyl) 2 (1h imidazol 1 yl)ethyl phenoxyacetate; 1 (4 fluorophenyl) 2 (1h imidazol 1 yl) 1 phenylethyl [4 (propan 2 yl)phenyl]carbamate; 1 (4 fluorophenyl) 2 (1h imidazol 1 yl)ethyl 3 (trifluoromethyl)benzoate; 1 (4 fluorophenyl) 2 (1h imidazol 1 yl)ethyl biphenyl 4 carboxylate; 1 (4 fluorophenyl) 2 (1h imidazol 1 yl)ethyl phenoxyacetate; 1 (4 trifluorophenyl) 2 (1h imidazol 1 yl)ethyl 3 (trifluoromethyl)benzoate; 2 (1h imidazol 1 yl) 1 phenylethanol derivative; 2 (1h imidazol 1 yl) 1 phenylethyl 3 (trifluoromethyl)benzoate; 2 (1h imidazol 1 yl) 1 phenylethyl 4 (trifluoromethyl)benzoate; 2 (1h imidazol 1 yl) 1 phenylethyl [4 (propan 2 yl)phenyl]carbamate; 2 (1h imidazol 1 yl) 1 phenylethyl biphenyl 4 carboxylate; 2 (1h imidazol 1 yl)ethanol; antifungal agent; carbamic acid derivative; ester derivative; fluconazole; imidazole derivative; unclassified drug; antifungal activity; article; Candida; Candida albicans; Candida krusei; controlled study; cytotoxicity; drug screening; drug synthesis; enantiomer; fungal strain; human; human cell; minimum inhibitory concentration; monocyte; nonhuman; racemic mixture; Antifungal Agents; Candida; Candida albicans; Candidiasis; Cell Line; Humans; Imidazoles; Microbial Sensitivity Tests; Phenylethyl Alcohol
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