Egger, Michael and Maity, Prantik and Hübner, Melanie and Seifert, Roland and König, Burkhard (2009) Synthesis and pharmacological properties of new tetracyclic forskolin analogues. European Journal of Organic Chemistry 2009 (21), pp. 3613-3618.
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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.
|Institutions:|| Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König|
Chemistry and Pharmacy > Institute of Pharmacy > Pharmacology and Toxicology (Prof. Schlossmann formerly Prof. Seifert)
|Projects:||GRK 760, Graduiertenkolleg Medizinische Chemie|
|Keywords:||Medicinal chemistry; Biological activity; Fused-ring systems; Carbenes; Rearrangement|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Created at the University of Regensburg:||Yes|
|Deposited On:||26 Aug 2009 09:40|
|Last Modified:||25 Oct 2010 10:12|
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