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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

Abstract: 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.
Cite: 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 OpenAlex
Dates:
Submitted: Apr 1, 2022
Published online: Sep 23, 2022
Identifiers:
Web of science: WOS:000857281700008
Elibrary: 51560931
OpenAlex: W4297017265
Citing:
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Web of science 3
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