Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity.
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.
Vasilevsky
Sergey F
SF
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
Govdi
Anastasiya I
AI
Shults
El'vira E
EE
Shakirov
Makhmut M
MM
Sorokina
Irina V
IV
Tolstikova
Tatyana G
TG
Baev
Dmitry S
DS
Tolstikov
Genrikh A
GA
Alabugin
Igor V
IV
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
D000114:Acetylene; D000893:Anti-Inflammatory Agents; D004798:Enzymes; D009828:Oleanolic Acid; C118308:betulonic acid; D000094062:Betulinic Acid