Synthesis and biological evaluation of new niphathesine analogues.
Niphathesine C and related pyridine alkaloids are well known natural products with interesting antimicrobial activities, characterized by a pyridine ring and a lipophilic side chain with a terminal nitrogen-containing functional group. This paper describes the synthesis of analogues of these alkylpyridine alkaloids with variation of the heterocyclic ring and the terminal functional group. Key steps of the syntheses are a Sonogashira reaction of appropriate aryl iodides with undec-10-ynol or undec-10-ynoic acid derivatives. The resulting compounds were tested in an agar diffusion assay against several bacteria and fungi.
Krauss
Jürgen
J
Department Pharmazie, Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, München, Germany. hjkra@cup.uni-muenchen.de
Wetzel
Christine
C
Thiel
Julia
J
Neudert
Christine
C
Bracher
Franz
F
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D000473:Alkanes / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects / Q000254:growth & development; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology
D000470:Alkaloids; D000473:Alkanes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D011725:Pyridines; C492790:niphatesine C