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SYNTHESIS AND ANALGESIC ACTIVITY OF 1-[(1,2,3-TRIAZOL-1-YL)METHYL]QUINOLIZINES BASED ON THE ALKALOID LUPININE

Жангельды С. Нурмаганбетов, Виктор А. Савельев, Юрий В. Гатилов, Оралгазы A. Нуркенов, Роза Б. Сейдахметова, Зарина Т. Шульгау, Гулим К. Мукушева, Серик Д. Фазылов, Эльвира Э. Шульц
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Abstract


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.

 


Keywords


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

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