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| Dokumentenart: | Artikel | ||||
|---|---|---|---|---|---|
| Titel eines Journals oder einer Zeitschrift: | Bioorganic & medicinal chemistry | ||||
| Verlag: | Elsevier | ||||
| Band: | 16 | ||||
| Nummer des Zeitschriftenheftes oder des Kapitels: | 8 | ||||
| Seitenbereich: | S. 4286-4293 | ||||
| Datum: | 2008 | ||||
| Zusätzliche Informationen (Öffentlich): | CAN 149:94684 1-3 Pharmacology 6754-58-1P (Xanthohumol); 62014-87-3P (Helichrysetin); 115063-39-3P (Desmethylxanthohumol); 123316-63-2P; 265659-35-6P (Xanthogalenol); 852638-41-6P; 1034276-26-0P; 1034276-27-1P; 1034276-28-2P; 1034276-29-3P; 1034276-30-6P; 1034276-31-7P; 1034276-32-8P Role: PAC (Pharmacological activity), SPN (Synthetic preparation), THU (Therapeutic use), BIOL (Biological study), PREP (Preparation), USES (Uses) (prepn and antitumor, antioxidant structure activity of natural and non-natural prenylated chalcones); 90-24-4; 100-83-4 (3-Hydroxybenzaldehyde); 120-14-9 (3,4-Dimethoxybenzaldehyde); 480-66-0; 870-63-3 (Prenyl bromide); 5533-04-0; 6515-06-6; 6515-21-5; 7507-89-3; 13057-17-5 (Methoxymethyl bromide); 13709-05-2; 24677-78-9 (2,3-Dihydroxybenzaldehyde); 76280-61-0; 90632-20-5; 126624-43-9; 160624-22-6; 404597-94-0; 955950-40-0; 1034276-41-9; 1034276-42-0; 1034276-43-1; 1034276-44-2 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn and antitumor, antioxidant structure activity of natural and non-natural prenylated chalcones); 30403-01-1P; 33523-62-5P; 65490-09-7P; 955950-41-1P; 1034276-33-9P; 1034276-34-0P; 1034276-35-1P; 1034276-36-2P; 1034276-37-3P; 1034276-38-4P; 1034276-39-5P; 1034276-40-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn and antitumor, antioxidant structure activity of natural and non-natural prenylated chalcones) | ||||
| Institutionen: | Chemie und Pharmazie > Institut für Pharmazie > Lehrstuhl Pharmazeutische Biologie (Prof. Heilmann) | ||||
| Identifikationsnummer: |
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| Stichwörter / Keywords: | Carcinoma Cervix (cervical carcinoma prepn and antitumor, antioxidant structure activity of natural and non-natural prenylated chalcones) Antioxidants Antitumor agents Human Structure-activity relationship (prepn and antitumor, antioxidant structure activity of natural and non-natural prenylated chalcones) antitumor antioxidant prenylated chalcone prepn structure activity | ||||
| 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: | 17243 |
Zusammenfassung
A general strategy for the synthesis of 3'-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones ...
Zusammenfassung
A general strategy for the synthesis of 3'-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2',3,4',5-tetrahydroxy-6'-methoxy-3'-prenylchalcone (9, IC50 3.2+-0.4 micro M) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5+-0.5 micro M), were more active in comparison to 1 (IC50 9.4+-1.4 micro M). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2+-0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8+-2.1) showed that the prenyl side chain at C-3' has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated deriv. This offers interesting synthetic possibilities for the development of more potent compds. The ORAC activity of the synthesized compds. was also investigated and revealed the highest activity for compds. 12, 4'-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4+-0.6, 3.8+-0.4, and 3.8+-0.5 Trolox equiv., resp.
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