ChemInform Abstract: SYNTHESIS OF 4‐OXO‐3,4,5,6‐TETRAHYDROAZEPINO(4,5‐B)INDOLES

Кост, А. Н.; Gorbunov, V. I.; Gorbunova, S. M.

doi:10.1002/chin.197650287

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“…1,3-Dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-(1-methylethyl)-2H-imidaz ol-2-one (17). A mixture of compound 16 36 (95 g, 0.23 mol), N -(2,2-dimethoxyethyl)- 2-propaneamine (49 g, 0.23 mol), DMAP (17.6 g, 0.144 mol), and triethylamine (66 mL) in dioxane (880 mL) was refluxed for 4 h. The mixture was cooled to room temperature, and H 2 O (880 mL) was added and stirred for 15 min. The precipitate was filtered, washed with H 2 O (2 × 50 mL), and dried under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and in Vitro and in Vivo Structure−Activity Relationships of Novel Antifungal Triazoles for Dermatology

et al. 2005

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In search for new compounds with potential for clinical use as antifungal agents in dermatology, a series of 12 azole compounds were synthesized stereospecifically and investigated specifically for their activity against dermatophyte fungal infections in animal models. This panel of azoles was studied in vitro and compared with itraconazole and terbinafine for their antifungal activity using a panel of 24 Candida spp. and 182 dermatophyte isolates. Three azoles (1c, 2c, and 4c) showed in vitro antifungal potency equivalent to itraconazole, but superior to terbinafine, against a panel of 24 Candida spp. with comparable or lower activity than that of itraconazole and terbinafine against 182 dermatophyte isolates and only rare activity against other pathogenic fungi. However, in vivo 1c and 4c, both given orally, demonstrated antifungal activity at least three times greater than itraconazole and were superior compared to terbinafine in M. canis infected guinea pigs. In a mouse model infected by T. mentagrophytes, again 4c, but not 1c, showed 5-fold superior activity over itraconazole and terbinafine. Compound 2c was effective in both models but less effective than itraconazole in these models. On the basis of these promising results, 4c is currently being clinically investigated for its potential as a novel antifungal agent against dermatophytosis.

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Section: Methodsmentioning

confidence: 99%