Synthesis and antimicrobial activity of N-analogous corollosporines.
Corollosporine is an antimicrobial metabolite, which was isolated from the marine fungus Corollospora maritima. Owing to its basic 4-hydroxyphthalic acid anhydride structure, it has become an attractive target for a structure/activity relationship modelling of derived compounds with potential antibiotic activity. In this regard we report on the straightforward synthesis of hetero analogous corollosporines, which were easily prepared by a three-step reaction sequence, taking advantage of a novel multicomponent reaction (AAD-reaction) and a subsequent aromatization/Grignard reaction protocol. Furthermore, the obtained products were tested in several biological assays to evaluate their antimicrobial activity.
Neumann
Helfried
H
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany.
Strübing
Dirk
D
Lalk
Michael
M
Klaus
Stefan
S
Hübner
Sandra
S
Spannenberg
Anke
A
Lindequist
Ulrike
U
Beller
Matthias
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D010796:Phthalic Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D010796:Phthalic Anhydrides; C114766:corollosporine