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SAR Studies of the Leupyrrins: Design and Total Synthesis of Highly Potent Simplified Leupylogs |
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| Authors: | Dr. Paul R. Wosniok Christopher Knopf Dr. Sandra Dreisigacker J. Manuel Orozco-Rodriguez Bettina Hinkelmann Prof. Dr. Peter P. Mueller Prof. Dr. Mark Brönstrup Prof. Dr. Dirk Menche |
| Affiliation: | 1. Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Current address: Eurofins Umwelt West GmbH Wesseling, Vorgebirgsstrasse 20, 50389 Wesseling, Germany;2. Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Current address: Eurofins Umwelt West GmbH Wesseling, Eurofins Genomics Europe Synthesis GmbH, Anzinger Str. 7a, 85560 Ebersberg, Germany;3. Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany Current address: HWI pharma services GmbH, Rheinzaberner Straße 8, 76761 Ruelzheim, Germany;4. Helmholtz Centre for Infection Research, Inhoffenstraße 7, 38124 Braunschweig, Germany;5. Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany |
| Abstract: | Leupyrrins are highly potent antifungal agents. A structure–activity-relationship study of natural and synthetic derivatives is reported which reveals important insights into the biological relevance of several structural subunits leading to the discovery of highly potent but drastically simplified leupylogs that incorporate a stable and readily available aromatic side chain. For their synthesis a concise strategy is described that enables a short and versatile access. |
| Keywords: | antifungal agents Leupylogs natural products SAR studies total synthesis |