A new approach towards ikimine A analogues.
An analogon of the alkylpyridine alkaloid ikimine A (1) was prepared in six steps starting from undec-10-ynoic acid. A key step in this synthesis was a Sonogashira coupling of the alkyne and 3-iodopyridine, followed by hydrogenation of the alkyne, reduction of the ester to the primary alcohol and oxidation to the corresponding aldehyde. This aldehyde was converted to the ikimine A analogon with O-methyl hydroxylamine hydrochloride. This product and the intermediate alkylpyridines were tested in the agar diffusion assay for antibacterial and antifungal activities.
Krauss
Jürgen
J
Department Pharmazie-Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 Munich, Germany. juergen.krauss@cup.uni.muenchen.de
Wetzel
Isolde
I
Bracher
Franz
F
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001230:Aspergillus / Q000187:drug effects; D041221:Candida glabrata / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008517:Phytotherapy; D011161:Porifera; D011549:Pseudomonas / Q000187:drug effects; D011725:Pyridines / Q000138:chemical synthesis*; D041181:Staphylococcus hominis / Q000187:drug effects; D025062:Yarrowia / Q000187:drug effects
D000470:Alkaloids; D000890:Anti-Infective Agents; D011725:Pyridines; C490049:ikimine A