title: Synthesis of dammarane-type triterpenoids with anti-inflammatory activity in vivo.
abstract: 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.
authors.affiliation: Novartis Institute for Biomedical Research, A-1230 Vienna, Austria. dieter.scholz@pharma.novartis.com
authors.forename: Dieter
authors.initials: D
authors.lastname: Scholz
authors.forename: Karl
authors.initials: K
authors.lastname: Baumann
authors.forename: Max
authors.initials: M
authors.lastname: Grassberger
authors.forename: Barbara
authors.initials: B
authors.lastname: Wolff-Winiski
authors.forename: Grety
authors.initials: G
authors.lastname: Rihs
authors.forename: Hansrudolf
authors.initials: H
authors.lastname: Walter
authors.forename: Josef G
authors.initials: JG
authors.lastname: Meingassner
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D017449:Dermatitis, Allergic Contact / Q000188:drug therapy / Q000473:pathology; D004195:Disease Models, Animal; D004305:Dose-Response Relationship, Drug; D004355:Drug Stability; D007166:Immunosuppressive Agents / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D013552:Swine; D014315:Triterpenes / Q000138:chemical synthesis / Q000494:pharmacology*; D000097669:Dammaranes
chemical_list: D000893:Anti-Inflammatory Agents; D007166:Immunosuppressive Agents; D014315:Triterpenes; D000097669:Dammaranes