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Synthesis of dammarane-type triterpenoids with anti-inflammatory activity in vivo.

Scholz, Dieter, Baumann, Karl, Grassberger, Max, Wolff-Winiski, Barbara, Rihs, Grety, Walter, Hansrudolf and Meingassner, Josef (2004) Synthesis of dammarane-type triterpenoids with anti-inflammatory activity in vivo. Bioorganic & Medicinal Chemistry Letters, 14 (11). pp. 2983-2986. ISSN 0960-894X


The 17-alpha-substituted triterpene 1 [(17alpha)-23-(E)-dammara-20,23-diene-3beta,25-diol] showed promising activity in animal models of immunosuppression and inflammation. Using a mouse model for inflammatory skin diseases (oxazolone-induced allergic contact dermatitis, ACD) as the directing in vivo test system, Structure-activity-relationship studies with the aim to understand the necessary structural requirements for the biological activity of 1 were conducted. Furthermore, we anticipated to identify biologically active compounds with the 17beta configuration, which are thermodynamically more stable and much easier to synthesize. This was achieved by identifying the 17-beta substituted dammarane 5B and its analogues.

Item Type: Article
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Additional Information: author can archive post-print (ie final draft post-refereeing); Publisher's version/PDF cannot be used
Keywords: Anti-inflammatory; Immunosuppressive; Allergic contact dermatitis; Triterpene; Triterpenoids; Dammar resin; Dammarane; Wittig
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Date Deposited: 14 Dec 2009 14:01
Last Modified: 31 Jan 2013 01:20


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