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新型N-烷基四氢和十氢异喹啉的合成与生物学评价：靶向麦角甾醇生物合成的新型抗真菌剂。

Synthesis and biological evaluation of novel N-alkyl tetra- and decahydroisoquinolines: novel antifungals that target ergosterol biosynthesis.

作者信息

Krauss Jürgen, Müller Christoph, Kießling Julia, Richter Sabine, Staudacher Verena, Bracher Franz

机构信息

Department of Pharmacy, Center for Drug Research, Ludwig-Maximilians-University Munich, Munich, Germany.

出版信息

Arch Pharm (Weinheim). 2014 Apr;347(4):283-90. doi: 10.1002/ardp.201300338. Epub 2014 Jan 27.

DOI:10.1002/ardp.201300338
PMID:24464607
Abstract

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 C11-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.

摘要

以相应的仲胺为起始原料，通过与烷基溴进行N-烷基化反应，合成了一系列N-烷基反式十氢异喹啉、1,2,3,4-四氢异喹啉和6,7-二甲氧基-1,2,3,4-四氢异喹啉衍生物。具有C11-烷基链的化合物表现出与克霉唑相当的抗真菌效力，并根据杂环骨架和所研究的物种抑制麦角甾醇生物合成的酶（Δ14-还原酶和Δ8,7-异构酶）。

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