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

Autores: 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
Afiliações:
1. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
2. Novosibirsk State University
Edição: Volume 512, Nº 1 (2023)
Páginas: 32-38
Seção: CHEMISTRY
URL: https://cardiosomatics.ru/2686-9535/article/view/651948
DOI: https://doi.org/10.31857/S2686953522600751
EDN: https://elibrary.ru/UYUMVC
ID: 651948

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Resumo

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.

Palavras-chave

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

Bibliografia

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