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Sci. Pharm. 2015, 83(1), 1-14; doi:10.3797/scipharm.1409-13

Synthesis and Antifungal Evaluation of Novel N-Alkyl Tetra- and Perhydroquinoline Derivatives

Department of Pharmacy – Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5–13, 81377 Munich, Germany
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Received: 21 September 2014 / Accepted: 22 November 2014 / Published: 22 November 2014
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Abstract

A series of novel N-alkyl tetra- and perhydroquinoline derivatives and their hydrochlorides were prepared from tetrahydro- or trans-perhydroquinoline by direct alkylation with alkyl halides and subsequent precipitation with HCl gas. The antimicrobial activity of the resulting amines was evaluated in an agar diffusion assay. The minimal inhibitory concentrations (MIC) of the active com-pounds were determined by the microdilution method. In contrast to the tetra-hydroquinolines, the perhydro analogues showed significant antifungal activity. In an assay for the detection of target enzymes in ergosterol biosynthesis, N-undecylperhydroquinoline was identified as an inhibitor of Δ8,7-isomerase.
Keywords: Quinoline; Antifungal activity; Ergosterol biosynthesis; Δ8,7-Isomerase; Enzyme inhibitor Quinoline; Antifungal activity; Ergosterol biosynthesis; Δ8,7-Isomerase; Enzyme inhibitor
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

KRAUß, J.; HORNACEK, M.; MÜLLER, C.; STAUDACHER, V.; STADLER, M.; BRACHER, F. Synthesis and Antifungal Evaluation of Novel N-Alkyl Tetra- and Perhydroquinoline Derivatives. Sci. Pharm. 2015, 83, 1-14.

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