title: Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity.
abstract: The Sonogashira reaction can be applied for the preparation of acetylenic derivatives of betulonic acid where the triterpenoid moiety can serve as either the halo- or the acetylenic component. This reaction opened access to the first derivatives of betulonic acid containing either the arylethynyl (C[triple bond]C-Ar(Het) or the ethynyl (C[triple bond]CH) moieties. From the fundamental perspective, this work illustrates the possibility of selective Pd-catalyzed cross-coupling at terminal acetylenes in the presence of a terminal alkene. Hepatoprotective and anti-inflammatory properties of selected acetylenic derivatives of betulonic acid were investigated using the CCl4-induced hepatitis and carrageenan-induced edema models, respectively.
authors.affiliation: Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya str., 630090 Novosibirsk, Russian Federation. vasilev@kinetics.nsc.ru
authors.forename: Sergey F
authors.initials: SF
authors.lastname: Vasilevsky
authors.forename: Anastasiya I
authors.initials: AI
authors.lastname: Govdi
authors.forename: El'vira E
authors.initials: EE
authors.lastname: Shults
authors.forename: Makhmut M
authors.initials: MM
authors.lastname: Shakirov
authors.forename: Irina V
authors.initials: IV
authors.lastname: Sorokina
authors.forename: Tatyana G
authors.initials: TG
authors.lastname: Tolstikova
authors.forename: Dmitry S
authors.initials: DS
authors.lastname: Baev
authors.forename: Genrikh A
authors.initials: GA
authors.lastname: Tolstikov
authors.forename: Igor V
authors.initials: IV
authors.lastname: Alabugin
mesh_terms: D000114:Acetylene / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use*; D056486:Chemical and Drug Induced Liver Injury / Q000188:drug therapy*; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D004798:Enzymes / Q000097:blood; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy; D008297:Male; D051379:Mice; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use; D000094062:Betulinic Acid
chemical_list: D000114:Acetylene; D000893:Anti-Inflammatory Agents; D004798:Enzymes; D009828:Oleanolic Acid; C118308:betulonic acid; D000094062:Betulinic Acid