title: An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester): analogues, biological activities, and comparison with oleanolic acid derivatives.
abstract: An efficient synthesis of methyl 2-cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-methyl ester) from commercially available ursolic acid, which features an oxidative ozonolysis-mediated C-ring enone formation, and provides the first access to ursolic acid-derived cyano enone analogues with C-ring activation. These new ursolic acid analogues show potent biological activities, with potency of approximately five-fold less than the corresponding oleanolic acid derivatives.
authors.affiliation: Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA. ggribble@dartmouth.edu.
authors.forename: Liangfeng
authors.initials: L
authors.lastname: Fu
authors.forename: Qi-Xian
authors.initials: QX
authors.lastname: Lin
authors.forename: Karen T
authors.initials: KT
authors.lastname: Liby
authors.forename: Michael B
authors.initials: MB
authors.lastname: Sporn
authors.forename: Gordon W
authors.initials: GW
authors.lastname: Gribble
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D004952:Esters; D020128:Inhibitory Concentration 50; D007371:Interferon-gamma / Q000494:pharmacology; D008264:Macrophages / Q000166:cytology / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D009828:Oleanolic Acid / Q000737:chemistry* / Q000494:pharmacology; D053978:Pentacyclic Triterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology; D000097245:Ursolic Acid
chemical_list: D000890:Anti-Infective Agents; D004952:Esters; D007371:Interferon-gamma; D009569:Nitric Oxide; D009828:Oleanolic Acid; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000097245:Ursolic Acid