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

Authors

  • Жангельды С. Нурмаганбетов 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
  • Виктор А. Савельев N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Юрий В. Гатилов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
  • Оралгазы A. Нуркенов Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan
  • Роза Б. Сейдахметова Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan
  • Зарина Т. Шульгау National Center for Biotechnology, 13/5 Kurgalzhynskoe Road, Nur-Sultan 010000, Kazakhstan
  • Гулим К. Мукушева Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan
  • Серик Д. Фазылов Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan
  • Эльвира Э. Шульц N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

DOI:

https://doi.org/10.1007/6330

Keywords:

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

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.

 

Author Biographies

Жангельды С. Нурмаганбетов, 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

Институт органического синтеза и углехимии Республики Казахстан, старший научный сотрудник

Виктор А. Савельев, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

Старший научный сотрудник лаборатории медицинской химии

Юрий В. Гатилов, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

ведущий научный сотрудник группы РСА

Оралгазы A. Нуркенов, Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan

Институт органического синтеза и углехимии Республики Казахстан, заведующий лабораторией

Роза Б. Сейдахметова, Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan

снс группы фармакологии

Зарина Т. Шульгау, National Center for Biotechnology, 13/5 Kurgalzhynskoe Road, Nur-Sultan 010000, Kazakhstan

Зав лабораторией токсикологии и фармакологии НЦБ РК

Гулим К. Мукушева, Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan

Институт органического синтеза и углехимии Республики Казахстан, старший научный сотрудник

Серик Д. Фазылов, Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, 1 Alikhanova St., Karaganda 100012, Kazakhstan

Институт органического синтеза и углехимии Республики Казахстан, заведующий лабораторией

Эльвира Э. Шульц, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia

зав. Лабораторией медицинской химии

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Published

2021-09-22

Issue

Vol. 57 No. 9 (2021)

Section

Original Papers