A new and facile synthesis of rutaecarpine alkaloids
Journal
Heterocycles
Journal Volume
78
Journal Issue
4
Pages
1047-1056
Date Issued
2009
Author(s)
CHE-MING TENG
Abstract
Relevant rutaecarpine analogues (1a-d) have been synthesized efficiently from the ring opened β-carboline derivatives (3a-d) as key intermediates.A unique one-pot reductive-cyclization as key reaction furnished the synthesis of rutaecarpine alkaloids in excellent yields.The key intermediates (3a-d) were prepared from tryptamine following acylation, Bischler-Napieralski cyclization, benzoylation, and oxidative cleavage of the exocyclic double bond.This new synthetic approach provides a facile access to rutaecarpine analogues with potent inhibitory effect on platelet aggregation.3][4][5] For instance, they are used in Chinese herbal medicine under the name Wu-Chu-Yu for remedy such as headache, dysentery, cholera, worm infections and postpartum. 6taecarpine and its analogues were also found to possess anti-stomachic, anti-emetic, anti-nociceptive, anti-inflammatory, anti-pyretic, analgesic, astringent, anti-hypertensive, uterotonic, cycloxygenase (COX-2) inhibitory and agonist TCDD-receptor activities. 7Furthermore, rutaecarpine can also suppress platelet plug formation in mesenteric venules and increase intracellular Ca 2+ in endothelial cells . 8Recently,
SDGs
Type
journal article