Synthesis and antifungal activities of (2R,3R)-2-aryl-1-azolyl-3-(substituted amino)-2-butanol derivatives as topical antifungal agents.

2-Aryl-1-azolyl-3-(substituted amino)-2-butanol derivatives I were prepared by ring-opening reaction of epoxides II with excess amine, and their antifungal activities were evaluated as topical agents. Azolyl-cyclic amine derivatives with a methylene group showed extremely strong activity with a broad spectrum in vitro. In general, anti-Trichophyton mentagrophytes activities of most of the topical antifungal agents are substantially reduced by addition of keratin (a major constituent of the keratinized tissue). However, the triazole derivative (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidino)-1-(1H-1,2 ,4- triazol-1-yl)-2-butanol ((-)-40, KP-103) showed very little deactivation by addition of keratin. This biological characteristic of triazole derivative (-)-40 resulted in excellent therapeutic efficacy on dermatophytosis superior to that of the corresponding imidazole derivative ((-)-41).
AuthorsH Ogura, H Kobayashi, K Nagai, T Nishida, T Naito, Y Tatsumi, M Yokoo, T Arika
JournalChemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 47 Issue 10 Pg. 1417-25 (Oct 1999) ISSN: 0009-2363 [Print] JAPAN
PMID10553638 (Publication Type: Journal Article)
Chemical References
  • Anti-Infective Agents, Local
  • Antifungal Agents
  • Butanols
  • Triazoles
  • Animals
  • Anti-Infective Agents, Local (chemical synthesis, therapeutic use)
  • Antifungal Agents (chemical synthesis, therapeutic use)
  • Butanols (chemical synthesis, pharmacology, therapeutic use)
  • Combinatorial Chemistry Techniques
  • Guinea Pigs
  • Hair
  • Male
  • Microbial Sensitivity Tests
  • Models, Chemical
  • Tinea (drug therapy)
  • Triazoles (chemical synthesis, pharmacology, therapeutic use)

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