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Synthesis and Structure–Activity Relationships of Novel Benzylamine‐Type Antifungals as Butenafine‐Related Antimycotics
Author(s) -
Krauss Jürgen,
Stadler Martina,
Bracher Franz
Publication year - 2017
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201600342
Subject(s) - chemistry , benzylamine , dermatophyte , candida glabrata , clotrimazole , stereochemistry , organic chemistry , antifungal , microbiology and biotechnology , biology
Benzylamine‐type antimycotics like naftifine, butenafine, or terbinafine are a well‐known class of antimycotics since the 1980s. The following paper describes the synthesis and biological evaluation of a series of novel benzylamine‐type antimycotics characterized by an isooctyl side chain and various substituents at the benzylamine moiety. The compounds were prepared from benzaldehyde derivatives and 2‐amino‐6‐methylheptane by reductive amination with sodium triacetoxyborohydride and subsequent precipitation with hydrogen chloride. The antimycotic activity of the resulting compounds was evaluated in an agar diffusion assay against the yeasts C. glabrata and Yarrowia lipolytica , the mold Aspergillus niger and the dermatophyte H. burtonii . The compounds were also tested in a microdilution assay against the yeast Candida glabrata and the dermatophyte H. burtonii to determine the minimal inhibitory concentrations (MIC). Compounds with an aromatic ether side chain or a short alkyl ether side chain showed significant antimycotic activity against C. glabrata , comparable to terbinafine or clotrimazole.