Synthesis and structure-activity relationships of naphthalene-substituted derivatives of the allylamine antimycotic terbinafine
| Autor: | P Nussbaumer, A Stütz, H. Vyplel, I Leitner, K. Mraz, G Dorfstätter |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
Antifungal Agents
biology Tertiary amine Bicyclic molecule Substituent Microbial Sensitivity Tests Naphthalenes biology.organism_classification Candida parapsilosis Medicinal chemistry Allylamine Aspergillus fumigatus Structure-Activity Relationship chemistry.chemical_compound chemistry Drug Discovery Molecular Medicine Structure–activity relationship Moiety Terbinafine |
| Zdroj: | Journal of Medicinal Chemistry. 36:2810-2816 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00071a011 |
| Popis: | Derivatives of the allylamine antimycotic terbinafine (1) with varied substitution at the naphthalene ring system have been prepared, and their antifungal activity has been evaluated. In general, the potency is strongly dependent on the bulkiness of the substituent. Only hydrogen or in some cases fluorine are tolerated as substituents at positions 2-4 and 6-8 of the naphthalene moiety, whereas 5-substituents may be larger in size (F, Cl, Br, Me). Derivatives with fluorine at positions 3, 5, and 7 or chlorine at position 5 showed enhanced activity against yeasts relative to 1. This increase in sensitivity could be intensified by simultaneous introduction of two fluoro substituents at positions 5 and 7. Compound 7q demonstrated 8- to 16-fold improved potency against Aspergillus fumigatus, Candida albicans, and Candida parapsilosis. |
| Databáze: | OpenAIRE |
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