SYNTHESIS OF 1,3-OXAZINE DERIVATIVES BASED ON (–)-ISOPULEGOL USING THE RITTER REACTION AND STUDY OF THEIR ANALGESIC ACTIVITY

Authors

  • Николай С. Ли-Жуланов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090
  • Алла В. Павлова N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Дина В. Корчагина N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • 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
  • Константин П. Волчо N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090
  • Татьяна Г. Толстикова N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Нариман Ф. Салахутдинов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090

DOI:

https://doi.org/10.1007/5739

Keywords:

heterocycle, (–)-isopulegol, nitrile, oxazine, terpene, acid catalysis, analgesic activity

Abstract

The Ritter reaction between monoterpenoid (–)-isopulegol and nitriles in the presence of concentrated sulfuric acid or trifluoromethanesulfonic acid yielded a series of chiral 1,3-oxazine derivatives. When studying the analgesic activity of the synthesized compounds in vivo, it was found that 1,3-oxazine synthesized by the reaction of (–)-isopulegol with benzyl cyanide increases the time of latency of the animal in the hot plate test of thermal pain irritation, not inferior in effectiveness to the comparison drug diclofenac sodium.

Authors: Nikolai S. Li-Zhulanov, Alla V. Pavlova, Dina V. Korchagina, Yurii V. Gatilov, Konstantin P. Volcho*, Tatyana G. Tolstikova, Nariman F. Salakhutdinov

Downloads

Published

2020-08-20

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Original Papers