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Title: Antifungal Agents. 11.N-Substituted Derivatives of 1-[(Aryl)(4-aryl-1H-pyrrol-3yl)methyl]-1H-imidazole: Synthesis, Anti-Candida Activity, and QSAR Studies
Authors: Di Santo, Roberto
Tafi, Andrea 
Costi, Roberta
Botta, Maurizio 
Artico, Marino
Corelli, Federico 
Forte, Michela
Caporuscio, Fabiana
Angiolella, Letizia
Palamara, Anna Teresa
Issue Date: 2005
Project: None 
1-[(Aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazoles were recently reported by our group as potent anti-Candida agents belonging to the antifungal azole class. In the present paper the synthesis, anti-Candida activities, and QSAR studies on a novel series of N-substituted 1-[(aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazole derivatives are reported. The newly synthesized azoles were tested against 12 strains of Candida albicans together with bifonazole, miconazole, itraconazole, fluconazole, and compounds 1a, 1b, 3a, 3b, and 3c used as reference drugs. In general, tested derivatives showed good antifungal activities, and the most potent compound was 1d (MIC(90) = 0.032 microg/mL), which was from 4- to 250-fold more potent than reference drugs. Catalyst software was applied to develop a quantitative pharmacophore model to be used for the rational design of new antifungal azoles. Some key interactions, as well as excluded volumes, further to the coordination bond of azole antifungals with the demethylase enzyme, are highlighted.
ISSN: 0022-2623
DOI: 10.1021/jm048997u
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