Egger, Michael and Pellett, Patrina and Nickl, Kathrin and Geiger, Sarah and Graetz, Stephanie and Seifert, Roland and Heilmann, Joerg and Koenig, Burkhard (2008) Synthesis and Cannabinoid Receptor Activity of Ketoalkenes from Echinacea pallida and Nonnatural Analogues. CHEMISTRY-A EUROPEAN JOURNAL, 14 (35). pp. 10978-10984. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
Despite its popularity and widespread use, the efficacy of Echinacea products remains unclear and controversial. Among the various compounds isolated from Echinacea, ketoalkenes and ketoalkenynes exclusively found in the pale purple coneflower (E. pallida) are major components of the extracts. In contrast to E. purpurea alkamides, these compounds have not been synthesized and studied for immunostimulatory effects. We present a practical and useful synthetic approach to the ketoalkenes using palladium-catalyzed cross-coupling reactions and the pharmaceutical results at the human cannabinoid receptors. The synthetic route developed provides overall good yields for the ketoalkenes and is applicable to other natural products with similar 1.4-diene motifs. No significant activity was observed at either receptor, indicating that the ketoalkenes from E. pallida are not responsible for immunomodulatory effects mediated via the cannabinergic system. However, newly synthesized non-natural analogues showed micro-molar potency at both cannabinoid receptors.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | STEREOSELECTIVE-SYNTHESIS; ALKYLAMIDES; ALKAMIDES; CB2; cannabinoid receptors; cross-coupling; Echinacea pallida; palladium; total synthesis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical Biology (Prof. Heilmann) Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 11 Nov 2020 11:59 |
| Last Modified: | 11 Nov 2020 11:59 |
| URI: | https://pred.uni-regensburg.de/id/eprint/31587 |
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