Synthesis of 1,2,3-Triazolyl-Substituted Derivatives of the Alkaloids Sinomenine and Tetrahydrothebaine on Ring A and Their Analgesic Activity

摘要

The isoquinoline alkaloids 4-O-methylsinomenine and C-annelated tetrahydrothebaine were modified by addition of 1,2,3-triazolyl substituents in the C-1 position of the morphinane skeleton via a Cu-catalyzed reaction of 1-ethynyl-substituted alkaloid derivatives with various azides. Analgesic activity in a chemical irritation model was found for 1-triazolyl-substituted derivatives of 6,7,8,14-tetrahydrothebaine.