Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine

Nurmaganbetov Z.S. Savelyev V.A. Gatilov Y.V. Nurkenov O.A. Seidakhmetova R.B. Shulgau Z.T. Mukusheva G.K. Fazylov S.D. Shults E.E.
September 2021 Springer

Chemistry of Heterocyclic Compounds
2021 #57 Issue 9 911 - 919 pp.

[Figure not available: see fulltext.] Modification of the quinolizine backbone of the alkaloid lupinine was carried out by introducing substituted 1,2,3-triazole. When NaN₃ acts upon the product of the reaction of lupinine with methanesulfonyl chloride, lupinyl azide is formed which in the reaction with terminal alkynes in the presence of aqueous CuSO₄ and sodium ascorbate forms the corresponding (1S,9aR)-1-[(1,2,3-triazol-1-yl)-methyl]octahydro-1H-quinolizines with various substituents at the C-4 position of the triazole ring. The structures of lupinine methanesulfonate and 1-[(1,2,3-triazol-1-yl)methyl]octahydroquinolizines were confirmed by X-ray structural analysis. 1-[(1,2,3-Triazol-1-yl)methyl]octahydroquinolizines containing a hydroxymethyl or 2-hydroxypropan-2-yl substituent at the C-4 position of the triazole ring exhibit pronounced analgesic activity.

azide-alkyne cycloaddition reaction , azides , quinolizine alkaloids , triazoles , X-ray structural analysis

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Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda, 100012, Kazakhstan
Karaganda Medical University, 40 Gogolya St., Karaganda, 100000, Kazakhstan
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russian Federation
National Center for Biotechnology, 13/5 Kurgalzhynskoe Road, Nur-Sultan, 010000, Kazakhstan

Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan
Karaganda Medical University
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
National Center for Biotechnology

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