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.
de Maris e Miranda
Leandro S
LS
Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Rio de Janeiro, RJ, Brazil.
Marinho
Bruno Guimarães
BG
Costa
Jeronimo S
JS
Leitão
Suzana G
SG
Santos
Tereza Cristina dos
TC
Monache
Franco Delle
FD
Fernandes
Patricia Dias
PD
Vasconcellos
Mário Luiz A A
ML
Pereira
Vera L Patrocinio
VL
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