Structural determination Vitex cymosa Bertero active principle: Diastereoselective synthesis of (+/-)-trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one and its antinociceptive activity.
The diastereoselective synthesis of (+/-)-trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one, as a mixture trans:cis (3:1), was accomplished using a protocol that combine the Prins cyclization and RuO(4) oxidation. The synthesis this lactone allowed the elucidation of the correct structure of the substance isolated from the barks of Vitex cymosa. The delta-lactones mixture showed significant antinociceptive properties in preliminary tests using the tail flick model assay.
Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Rio de Janeiro, RJ, Brazil.
Leandro S
LS
de Maris e Miranda
Bruno Guimarães
BG
Marinho
Jeronimo S
JS
Costa
Suzana G
SG
Leitão
Tereza Cristina dos
TC
Santos
Franco Delle
FD
Monache
Patricia Dias
PD
Fernandes
Mário Luiz A A
ML
Vasconcellos
Vera L Patrocinio
VL
Pereira
D000700:Analgesics / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use*; D000818:Animals; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use*; D015394:Molecular Structure; D010146:Pain / Q000188:drug therapy*; D013237:Stereoisomerism; D020950:Vitex / Q000737:chemistry*
D000700:Analgesics; D007783:Lactones