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Cross‐Coupling‐Cyclocondensation Reaction Sequence to Access a Library of Ring‐C Bridged Pyrimidino‐tetrahydrothebaines and Pyrimidinotetrahydrooripavines
Author(s) -
Finke Anastasija O.,
Ravaeva Marina Y.,
Krasnov Vyacheslav I.,
Cheretaev Igor V.,
Chuyan Ele.,
Baev Dmitry S.,
Shults Elvira E.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202101790
Subject(s) - ring (chemistry) , sequence (biology) , coupling (piping) , coupling reaction , chemistry , stereochemistry , computer science , materials science , organic chemistry , composite material , catalysis , biochemistry
Ring‐C bridged 1‐(pyrimidinyl)tetrahydrothebaines were convenience synthesized by a consecutive three‐component alkynylation–cyclocondensation sequence starting from 1‐ethynyl‐7α,8α‐(2,5‐dioxo‐N‐phenylpyrrolidino)‐[3,4‐ h ]‐6,14‐ endo ‐etheno‐tetrahydrothebaine, aroyl chlorides, and amidinium hydrochlorides. Several derivatizations and transformations of selected 1‐pyrimidinyl substituted tetrahydrothebaines were carried out. The analgesic activity of new type of hybrid compounds in the tail‐flick test in rats was evaluated. The data revealed that the antinociceptive potency was stroungly depended on the nature of the substituent in the C‐6 position of the pyrimidine nucleus. Docking study was undertaken to gain insight into the possible binding mode with the μ‐opioid receptor.