CHIRAL  N -(OCTAHYDRO-2 H -CHROMEN-4-YL)-2-(DIALKYLAMINO)ACETAMIDES: SYNTHESIS AND ANALGESIC ACTIVITY

N. S. Li-Zhulanov; Ли-Жуланов Н. С.; K. M. Nikolaichuk; Николайчук К. М.; Yu. V. Gatilov; Гатилов Ю. В.; K. P. Volcho; Волчо К. П.; M. V. Khvostov; Хвостов М. В.; T. G. Tolstikova; Толстикова Т. Г.; N. F. Salakhutdinov; Салахутдинов Н. Ф.

doi:10.31857/S2686953522600751

CHIRAL N-(OCTAHYDRO-2H-CHROMEN-4-YL)-2-(DIALKYLAMINO)ACETAMIDES: SYNTHESIS AND ANALGESIC ACTIVITY

Authors: Li-Zhulanov N.S.¹, Nikolaichuk K.M.¹^,2, Gatilov Y.V.¹, Volcho K.P.¹, Khvostov M.V.¹, Tolstikova T.G.¹, Salakhutdinov N.F.¹
Affiliations:
1. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
2. Novosibirsk State University
Issue: Vol 512, No 1 (2023)
Pages: 32-38
Section: CHEMISTRY
URL: https://journal-vniispk.ru/2686-9535/article/view/247178
DOI: https://doi.org/10.31857/S2686953522600751
EDN: https://elibrary.ru/UYUMVC
ID: 247178

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Abstract
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Abstract

Based on monoterpenoid (–)-isopulegol a number of new derivatives of octahydro-2H-chromene have been synthesized. The structure of the products obtained was determined by ¹H and ¹³C NMR spectroscopy, high resolution mass spectrometry and X-ray diffraction analysis. It was shown that several synthesized compounds exhibit high analgesic activity in in vivo tests. The highest efficiency in both tests (acetic writhing and hot plate) was shown by (4S)-diastereomers of morpholinoacetamide derivatives of octahydro-2H-chromene.

Keywords

isopulegol, Prins–Ritter reaction, octahydro-2H-chromene, analgesic activity

References

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