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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Chemistry: a European journal | ||||
| Verlag: | Wiley-VCH | ||||
| Band: | 14 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 35 | ||||
| Seitenbereich: | S. 10978-10987 | ||||
| Datum: | 2008 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 150:237281 26-9 Biomolecules and Their Synthetic Analogs 13965-03-2 (Bis(triphenylphosphine)dichloropalladium) Role: CAT (Catalyst use), USES (Uses) (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity); 1115909-04-0P Role: PAC (Pharmacological activity), RCT (Reactant), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation), RACT (Reactant or reagent) (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity); 149301-78-0P; 1115909-10-8P Role: PAC (Pharmacological activity), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity); 107-19-7 (Propargyl alcohol); 502-42-1 (Cycloheptanone); 506-32-1; 536-74-3; 590-13-6 ((Z)-1-Bromo-1-propene); 590-15-8 ((E)-1-Bromo-1-propene); 928-94-9 ((Z)-2-Hexen-1-ol); 1066-54-2; 6089-04-9 (1-(Tetrahydropyranyloxy)-2-propyne) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity); 3761-94-2P; 20739-58-6P (2-Octyn-1-ol); 26001-58-1P; 26806-12-2P; 36602-98-9P; 53384-66-0P; 56922-75-9P; 60099-86-7P; 66432-72-2P; 75359-52-3P; 80639-28-7P; 82168-14-7P; 108965-88-4P; 122712-60-1P; 343950-99-2P; 1115908-75-2P; 1115908-92-3P; 1115908-96-7P; 1115908-98-9P; 1115909-00-6P; 1115909-02-8P; 1115909-06-2P; 1115909-08-4P; 1115909-15-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity); 57221-86-0P; 116752-10-4P; 118853-86-4P; 118853-87-5P; 214041-70-0P; 1115909-12-0P; 1115909-17-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Structure-activity relationship (cannabinoid prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity) Cross-coupling reaction Cross-coupling reaction catalysts Echinacea pallida Human (prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity) Cannabinoid receptors Role: BSU (Biological study, unclassified), BIOL (Biological study) (type CB1 prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity) Cannabinoid receptors Role: BSU (Biological study, unclassified), BIOL (Biological study) (type CB2 prepn. of ketoalkenes from echinacea pallida and non-natural analogs by Pd-catalyzed cross-coupling and cannabinoid receptor activity) ketoalkene echinacea pallida synthesis analog cannabinoid receptor agonist cross coupling palladium ketoalkene synthesis | ||||
| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 570 Biowissenschaften, Biologie 500 Naturwissenschaften und Mathematik > 540 Chemie | ||||
| Status: | Veröffentlicht | ||||
| Begutachtet: | Ja, diese Version wurde begutachtet | ||||
| An der Universität Regensburg entstanden: | Ja | ||||
| Dokumenten-ID: | 17238 |
Zusammenfassung
Despite its popularity and widespread use, the efficacy of Echinacea products remains unclear and controversial. Among the various compds. isolated from Echinacea, ketoalkenes and ketoalkenynes exclusively found in the pale purple coneflower (E. pallida) are major components of the exts. In contrast to E. purpurea alkamides, these compds. have not been synthesized and studied for ...
Zusammenfassung
Despite its popularity and widespread use, the efficacy of Echinacea products remains unclear and controversial. Among the various compds. isolated from Echinacea, ketoalkenes and ketoalkenynes exclusively found in the pale purple coneflower (E. pallida) are major components of the exts. In contrast to E. purpurea alkamides, these compds. 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 obsd. 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 analogs showed micro-molar potency at both cannabinoid receptors.
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