Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones

Citation
T. Kitazaki et al., Optically active antifungal azoles. VIII. Synthesis and antifungal activity of 1-[(1R,2R)-2-(2,4-difluoro- and 2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-substituted phenyl)-2(1H,3H)-imidazolones and 2-imidazolidinones, CHEM PHARM, 47(3), 1999, pp. 351-359
Citations number
8
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
47
Issue
3
Year of publication
1999
Pages
351 - 359
Database
ISI
SICI code
0009-2363(199903)47:3<351:OAAAVS>2.0.ZU;2-I
Abstract
New optically active antifungal azoles, 1-[(1R,2R)-2-(2,4-difluoro- and 2-f luorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-(4-subst ituted phenyl)-2(1H,3H)-imidazolones (1, 2) and 2 -imidazolidin ones (3, 4) , were prepared in a stereocontrolled manner from (1S)-1-[(2R)-2-(2,4-diflu oro- and 2-fluorophenyl)-2-oxiranyl]ethanols (15, 16). Compounds 1-4 showed potent antifungal activity against Candida albicans in vitro and in vivo, as well as a broad antifungal spectrum for various fungi in vitro. Furtherm ore, the imidazolidinones, 3b-e and 4d, e, were found to exert extremely st rong growth-inhibitory activity against Aspergillus fumigatus.