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1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, New Imidazoles with Potent Activity againstCandida albicansand Dermatophytes. Synthesis, Structure−Activity Relationship, and Molecular Modeling Studies

Giuseppe La Regina, Felicia Diodata D’Auria, Andrea Tafi, Francesco Piscitelli, Stefania Olla, Fabiana Caporuscio, Lucia Nencioni, Roberto Cirilli, Francesco La Torre, Nadja Rodrigues De Melo, Steven Kelly Orcid Logo, David C. Lamb, Marino Artico, Maurizio Botta, Anna Teresa Palamara, Romano Silvestri

Journal of Medicinal Chemistry, Volume: 51, Issue: 13, Pages: 3841 - 3855

Swansea University Author: Steven Kelly Orcid Logo

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DOI (Published version): 10.1021/jm800009r

Abstract

New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketocona...

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Published in: Journal of Medicinal Chemistry
ISSN: 0022-2623 1520-4804
Published: American Chemical Society (ACS) 2008
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URI: https://cronfa.swan.ac.uk/Record/cronfa10336
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Abstract: New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 mu g/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC <= 5 mu g/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents.
Keywords: AZOLE ANTIFUNGAL AGENTS; ANTICANDIDA ACTIVITY; BINDING; DERIVATIVES; FLUOXETINE; RESISTANCE; ANALOGS; DRUGS; CYP51
College: Swansea University Medical School
Issue: 13
Start Page: 3841
End Page: 3855