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

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

Journal

Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388

Output data

Year: 2022, Volume: 58, Number: 5, Pages: 895-902 Pages count : 8 DOI: 10.1007/s10600-022-03824-5

Tags

alkaloids triazoles azide–alkyne cycloaddition reaction analgesic activity

Authors

Finke A.O. ¹ , Pavlova A.V. ¹ , Morozova E.A. ¹ , Tolstikova T.G. ¹ , Shults E.E. ¹

Affiliations

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences

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.

Finke A.O. , Pavlova A.V. , Morozova E.A. , Tolstikova T.G. , Shults E.E.
Synthesis of 1,2,3-Triazolyl-Substituted Derivatives of the Alkaloids Sinomenine and Tetrahydrothebaine on Ring A and Their Analgesic Activity
Chemistry of Natural Compounds. 2022. V.58. N5. P.895-902. DOI: 10.1007/s10600-022-03824-5 WOS РИНЦ

Submitted:	Apr 1, 2022
Published online:	Sep 23, 2022

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