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Synthesis and Biological Evaluation of Novel N ‐Alkyl Tetra‐ and Decahydroisoquinolines: Novel Antifungals that Target Ergosterol Biosynthesis
Author(s) -
Krauss Jürgen,
Müller Christoph,
Kießling Julia,
Richter Sabine,
Staudacher Verena,
Bracher Franz
Publication year - 2014
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.201300338
Subject(s) - chemistry , alkyl , clotrimazole , biosynthesis , ergosterol , alkylation , tetra , tetrahydroisoquinoline , potency , antifungal , stereochemistry , enzyme , biochemistry , in vitro , organic chemistry , medicinal chemistry , biology , microbiology and biotechnology , catalysis
A series of N ‐alkyl trans ‐decahydroisoquinoline, 1,2,3,4‐tetrahydroisoquinoline, and 6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline derivatives were synthesized starting from the respective secondary amines by N ‐alkylation with alkyl bromides. The compounds with C 11 ‐alkyl chains showed antifungal potency comparable to clotrimazole, and inhibit enzymes of the ergosterol biosynthesis (Δ14‐reductase and Δ8,7‐isomerase), depending on the heterocyclic scaffold and the investigated species.