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Cross-Coupling-Cyclocondensation Reaction Sequence to Access a Library of Ring-C Bridged Pyrimidino-tetrahydrothebaines and Pyrimidinotetrahydrooripavines Full article

Journal ChemistrySelect
ISSN: 2365-6549
Output data Year: 2021, Volume: 6, Number: 29, Pages: 7391-7397 Pages count : 7 DOI: 10.1002/slct.202101790
Tags alkaloids; alkynones; analgesic activity; cross-coupling reaction; (-)-thebaine
Authors Finke Anastasija O. 1 , Ravaeva Marina Y. 2 , Krasnov Vyacheslav I. 1 , Cheretaev Igor V. 2 , Chuyan Elena N. 2 , Baev Dmitry S. 1 , Shults Elvira E. 1
Affiliations
1 (Данные Web of science) Novosibirsk Organ Chem Inst, Lab Magnet Radiospect, Lab Pharmaceut Res, Lab Med Chem, Lavrentyev Ave 9, Novosibirsk 630090, Russia
2 (Данные Web of science) VI Vernadsky Crimean Fed Univ, Biol & Chem Dept, Vernadskogo Ave 4, Simferopol 295007, Russia

Abstract: Ring-C bridged 1-(pyrimidinyl)tetrahydrothebaines were convenience synthesized by a consecutive three-component alkynylation-cyclocondensation sequence starting from 1-ethynyl-7 alpha,8 alpha-(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 mu-opioid receptor.
Cite: Finke A.O. , Ravaeva M.Y. , Krasnov V.I. , Cheretaev I.V. , Chuyan E.N. , Baev D.S. , Shults E.E.
Cross-Coupling-Cyclocondensation Reaction Sequence to Access a Library of Ring-C Bridged Pyrimidino-tetrahydrothebaines and Pyrimidinotetrahydrooripavines
ChemistrySelect. 2021. V.6. N29. P.7391-7397. DOI: 10.1002/slct.202101790 WOS Scopus
Identifiers:
Web of science WOS:000680162200017
Scopus 2-s2.0-85111620110
OpenAlex W3188081970
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