Synthesis of 1,3-Oxazine Derivatives Based on (–)-Isopulegol using the Ritter Reaction and Study of their Analgesic Activity

Synthesis of 1,3-Oxazine Derivatives Based on (–)-Isopulegol using the Ritter Reaction and Study of their Analgesic Activity Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2020, Volume: 56, Number: 7, Pages: 936-941 Pages count : 6 DOI: 10.1007/s10593-020-02753-x

Tags

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

Authors

Li-Zhulanov N.S. ^1,2 , Pavlova A.V. ¹ , Korchagina D.V. ¹ , Gatilov Y.V. ¹ , Volcho K.P. ^1,2 , Tolstikova T.G. ¹ , Salakhutdinov N.F. ^1,2

Affiliations

1	(Scopus) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russian Federation
2	(Scopus) Novosibirsk State University, 2 Pirogova St, Novosibirsk, 630090, Russian Federation

[Figure not available: see fulltext.] 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. © 2020, Springer Science+Business Media, LLC, part of Springer Nature.

Li-Zhulanov N.S. , Pavlova A.V. , Korchagina D.V. , Gatilov Y.V. , Volcho K.P. , Tolstikova T.G. , Salakhutdinov N.F.
Synthesis of 1,3-Oxazine Derivatives Based on (–)-Isopulegol using the Ritter Reaction and Study of their Analgesic Activity
Chemistry of Heterocyclic Compounds. 2020. V.56. N7. P.936-941. DOI: 10.1007/s10593-020-02753-x WOS Scopus РИНЦ

Published print:	Jul 1, 2020
Published online:	Aug 21, 2020

Web of science	WOS:000561986600008
Scopus	2-s2.0-85089733949
Elibrary	45340618
OpenAlex	W3080207849