Egger, Michael and Maity, Prantik and Huebner, Melanie and Seifert, Roland and Koenig, Burkhard (2009) Synthesis and Pharmacological Properties of New Tetracyclic Forskolin Analogues. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (21). pp. 3613-3618. ISSN 1434-193X, 1099-0690
Full text not available from this repository. (Request a copy)Abstract
New tetracyclic analogues of forskolin have been prepared by derivatization of the natural product. Treatment of a forskolin-derived cyclic thionocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine resulted in the formation of a seven-membered cyclic carbonate derivative by an unprecedented rearrangement of an intermediate dialkoxycarbene or 1,3-dipole, whereas radical deoxygenation was followed by intramolecular cyclization with the double bond to form a third analogue. Two of the new analogues were investigated for their ability to activate adenylyl cyclases 1, 2 and 5 The introduction of another ring into the forskolin skeleton did not lead to a loss of binding affinity to the enzyme. Although the new compounds are much more spacious than forskolin, they still seem to fit into the binding pocket and were found to be partial agonists. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ADENYLYL-CYCLASE ISOFORMS; INHIBITION; DERIVATIVES; DIMETHOXYCARBENE; ACTIVATION; 1,2-DIOLS; Medicinal chemistry; Biological activity; Fused-ring systems; Carbenes; Rearrangement |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Sep 2020 04:43 |
| Last Modified: | 14 Sep 2020 04:43 |
| URI: | https://pred.uni-regensburg.de/id/eprint/28739 |
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