Synthetic derivatives of the alpha- and beta-amyrin triterpenes and their antinociceptive properties.
Fifteen different derivatives of an alpha- and beta-amyrin mixture were synthesized by acylation with appropriate anhydride or acid chlorides and oxidation in the presence of tert-butyl chromate or PCC. The molecular structures of the obtained compounds were confirmed by means of IR and (1)H NMR spectra. The compounds were screened for antinociceptive activity using the acetic acid pain model. The 3-O-acyl derivatives alpha- and beta-amyrin propionate 4, alpha- and beta-amyrin hexanoate 6, and alpha- and beta-amyrin octanoate 7 were found to be the most active compounds of the series. In addition, we also have found that alpha- and beta-amyrin octanoate 7 was able to reduce acetic acid-induced abdominal constriction when administered by oral route. Furthermore, this compound reduced the nociceptive response induced by intraplantar injection of formalin.
Soldi
Cristian
C
Departamento de Química, Centro de Ciências Físicas e Matemáticas, Universidade Federal de Santa Catarina, Campus Trindade, Florianópolis 88040-900, Santa Catarina, Brazil.
Pizzolatti
Moacir Geraldo
MG
Luiz
Ana Paula
AP
Marcon
Rodrigo
R
Meotti
Flavia Carla
FC
Mioto
Letícia Adelia
LA
Santos
Adair R S
AR
D000700:Analgesics / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D004195:Disease Models, Animal; D051379:Mice; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010146:Pain / Q000188:drug therapy*; D013329:Structure-Activity Relationship; D014315:Triterpenes
D000700:Analgesics; D014315:Triterpenes; D009828:Oleanolic Acid; C036380:beta-amyrin