title: Synthesis and Antifungal Evaluation of Novel N-Alkyl Tetra- and Perhydroquinoline Derivatives.
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 compounds were determined by the microdilution method. In contrast to the tetrahydroquinolines, 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.
authors.affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Krauß
authors.affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Michal
authors.initials: M
authors.lastname: Hornacek
authors.affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: MÜller
authors.affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Verena
authors.initials: V
authors.lastname: Staudacher
authors.affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Martina
authors.initials: M
authors.lastname: Stadler
authors.affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Franz
authors.initials: F
authors.lastname: Bracher
keywords: Antifungal activity; Enzyme inhibitor; Ergosterol biosynthesis; Quinoline; Δ8,7-Isomerase
references.citation: Steroids. 2013 May;78(5):483-93
references.pmid: 23454215
references.citation: Sci Pharm. 2013 Sep 02;81(3):641-50
references.pmid: 24106663
references.citation: J Immunol Methods. 1983 Dec 16;65(1-2):55-63
references.pmid: 6606682
references.citation: Clin Exp Dermatol. 1992 Sep;17 Suppl 1:8-12
references.pmid: 1458670
references.citation: Arch Pharm (Weinheim). 2014 Apr;347(4):283-90
references.pmid: 24464607
references.citation: J Vet Pharmacol Ther. 2003 Feb;26(1):5-29
references.pmid: 12603774