Researches on antibacterial and antifungal agents. IX--Pyrrole analogues of bifonazole with potent antifungal activities
Massa, S.; Stefancich, G.; Corelli, F.; Silvestri, R.; Panico, S.; Artico, M.; Simonetti, N.
Il Farmaco; Edizione Scientifica 43(9): 693-704
1988
ISSN/ISBN: 0430-0920 PMID: 3229495 Document Number: 310507
The synthesis and antifungal activities of pyrrole analogues of bifonazole are reported. Reduction of 4-nitrobenzophenone to the corresponding alcohol, reaction with phosphorus tribromide of the latter compound and condensation of the bromonitroderivative with imidazole led to 1-[alpha-(4-nitrophenyl)-4'-benzyl]-1H-imidazole. Hydrogenation of the nitro group to amino and reaction with 2,5-dimethoxytetrahydrofuran according to the Clauson-Kaas procedure afforded the pyrrole analogue of bifonazole. This compound and the related chloroderivative were also prepared by a similar pathway starting from 4-(1H-pyrrol-1-yl)benzophenone and its 4'-chloroderivative. Microbiological screening against Candida albicans and Candida spp showed 1-(alpha-[4-(1H-pyrrol-1-yl)phenyl]benzyl)-1H-imidazole to be the most active compound among the tested derivatives.