Chiral N-(Octahydro-2H-chromen-4-yl)-2-(dialkylamino)acetamides: Synthesis and Analgesic Activity

Chiral N-(Octahydro-2H-chromen-4-yl)-2-(dialkylamino)acetamides: Synthesis and Analgesic Activity Full article

Journal

Doklady Chemistry
ISSN: 0012-5008

Output data

Year: 2023, Volume: 512, Number: 1, Pages: 242-248 Pages count : 7 DOI: 10.1134/s0012500823600694

Tags

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

Authors

Li-Zhulanov N.S. ¹ , Nikolaichuk K.M. ^1,2 , Gatilov Yu.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

A number of new derivatives of octahydro-2H-chromene based on monoterpenoid (–)-isopulegol has been synthesized. The composition and structure of the products have been established using NMR spectroscopy, high-resolution mass spectrometry, and X-ray diffraction analysis. It has been shown that the majority of obtained compounds show high analgesic activity in vivo. (4S)‑Diastereomers of morpholinoacetamide derivatives of octahydro-2H-chromene showed the highest efficiency in both tests (acetic acid-induced writhing test and hot plate test).

Li-Zhulanov N.S. , Nikolaichuk K.M. , Gatilov Y.V. , Volcho K.P. , Khvostov M.V. , Tolstikova T.G. , Salakhutdinov N.F.
Chiral N-(Octahydro-2H-chromen-4-yl)-2-(dialkylamino)acetamides: Synthesis and Analgesic Activity
Doklady Chemistry. 2023. V.512. N1. P.242-248. DOI: 10.1134/s0012500823600694 Scopus РИНЦ

Ли-Жуланов Н.С. , Николайчук К.М. , Гатилов Ю.В. , Волчо К.П. , Хвостов М.В. , Толстикова Т.Г. , Салахутдинов Н.Ф.
Хиральные N-(октагидро-2H-хромен-4-ил)-2-(диалкиламино)ацетамиды: синтез и анальгетическая активность
Доклады Российской академии наук. Химия, науки о материалах.. 2023. Т.512. №1. С.32-38. DOI: 10.31857/S2686953522600751 РИНЦ

Submitted:	Nov 25, 2022
Accepted:	Jan 16, 2023
Published print:	Dec 25, 2023

Scopus	2-s2.0-85180717960
Elibrary	64393162
OpenAlex	W4390191010