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

Autor: Anna Teresa Palamara, Daniela De Vita, Barbara Di Rienzo, Luigi Scipione, Simona Panella, Roberto Cirilli, Giovanna Simonetti, Roberto Di Santo, Paolo Mellini, Silvano Tortorella, D'Auria Fd
Přispěvatelé: Department of Medicinal Chemistry and Technologies, Institut Pasteur, Fondation Cenci Bolognetti - Istituto Pasteur Italia, Fondazione Cenci Bolognetti, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome], Department of Public Health and Infectious Diseases, Dipartimento del Farmaco, Istituto Superiore di Sanita [Rome]
Rok vydání: 2012
Předmět:
Carbamate
Antifungal Agents
Stereochemistry
medicine.medical_treatment
Microbial Sensitivity Tests
01 natural sciences
Cell Line
03 medical and health sciences
chemistry.chemical_compound
MESH: Candida
Candida albicans
Drug Discovery
medicine
Humans
Cytotoxicity
Candida
030304 developmental biology
Pharmacology
Biphenyl
MESH: Microbial Sensitivity Tests
0303 health sciences
MESH: Humans
non-albicans candida species
human monocytic cell line
enantiomers separation
antifungal imidazoles
candida albicans species
Strain (chemistry)
biology
010405 organic chemistry
MESH: Candida albicans
Organic Chemistry
Candidiasis
Imidazoles
General Medicine
Phenylethyl Alcohol
[SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences
MESH: Antifungal Agents
biology.organism_classification
MESH: Candidiasis
Corpus albicans
MESH: Cell Line
3. Good health
0104 chemical sciences
chemistry
MESH: Phenylethyl Alcohol
Enantiomer
MESH: Imidazoles
Fluconazole
medicine.drug
Zdroj: European Journal of Medicinal Chemistry
European Journal of Medicinal Chemistry, Elsevier, 2012, 49, pp.334-42. ⟨10.1016/j.ejmech.2012.01.034⟩
ISSN: 0223-5234
1768-3254
DOI: 10.1016/j.ejmech.2012.01.034
Popis: International audience; 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).
Databáze: OpenAIRE
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