The preparation and antifungal properties of cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl-methyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine (I) are described. Ketoconazole has, at low oral doses, a high in vivi activity against vaginal candidosis in rats and against cutaneous candidosis in guinea pigs.
Synthesis of 1-[2-(arylalkyl)-2-phenylethyl]-1H-imidazoles was accomplished starting from the corresponding phenylacetonitriles. Via successive alkylation, conversion to the corresponding ester, and sodium borohydride-lithium iodide reduction, beta-phenylalcanols were obtained. These alcohols were mesylated and then refluxed with imidazole in dimethylformamide to yield the title compounds, which were active in vitro against dermatophytes, yeasts, other fungi, and gram-positive bacteria. Some were also active in vivo against Candida albicans.
min. ED+300% values are recorded in Table 1. ED+300% is defined as the dose at which the average sleeping time of the animals in a test group is increased by 300% in comparison to that of a control group.2. These nitro compounds themselves are synthesized as outlined in Scheme I. The reaction of p-nitrophenol with Scheme I
Phenylacetonitrile (I) werden mit NaH und Aralkylhalogeniden zu (II) substituiert und dann über freie Säuren (III), deren Ester (IV) und die reduktiv erhaltenen Hydroxymethyl‐Verbindungen (V) und ihre Mesylate (VI) mit Imidazol (VII) zu den Imidazolyl‐Verbindungen (VIII) kondensiert.
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