Cross-Coupling-Cyclocondensation Reaction Sequence to Access a Library of Ring-C Bridged Pyrimidino-tetrahydrothebaines and Pyrimidinotetrahydrooripavines Full article
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ChemistrySelect
ISSN: 2365-6549 |
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| 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 | ||||
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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 OpenAlex
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 OpenAlex
Identifiers:
| Web of science: | WOS:000680162200017 |
| Scopus: | 2-s2.0-85111620110 |
| OpenAlex: | W3188081970 |