Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity
V A Kuznetsova
2
,
Yu.V Gatilov
1
,
K P Volcho
1
,
M V Khvostov
1
,
T G Tolstikova
1
,
N. F. Salakhutdinov
1
Publication type: Journal Article
Publication date: 2023-10-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
A number of new octahydro-2H-chromene acetamide derivatives based on the monoterpenoid (−)-isopulegol were synthesized using a one-pot three-component Prins—Ritter reaction. The structure of the target compounds was determined using 1H and 13C NMR spectroscopy, high resolution mass spectrometry, and X-ray diffraction analysis. Most of the products exhibited high analgesic activity in in vivo tests. The highest analgesic activity was found for spirocyclic compound (4S)-2d, the effect of which is apparently mediated through the dopamine system. It was shown that compound (4S)-2d has a low acute toxicity.
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Total citations:
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Citations from 2024:
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Li-Zhulanov N. S. et al. Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity // Russian Chemical Bulletin. 2023. Vol. 72. No. 10. pp. 2430-2438.
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Li-Zhulanov N. S., Kuznetsova V. A., Gatilov Y., Volcho K. P., Khvostov M. V., Tolstikova T. G., Salakhutdinov N. F. Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity // Russian Chemical Bulletin. 2023. Vol. 72. No. 10. pp. 2430-2438.
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TY - JOUR
DO - 10.1007/s11172-023-4044-2
UR - https://doi.org/10.1007/s11172-023-4044-2
TI - Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity
T2 - Russian Chemical Bulletin
AU - Li-Zhulanov, N. S.
AU - Kuznetsova, V A
AU - Gatilov, Yu.V
AU - Volcho, K P
AU - Khvostov, M V
AU - Tolstikova, T G
AU - Salakhutdinov, N. F.
PY - 2023
DA - 2023/10/01
PB - Springer Nature
SP - 2430-2438
IS - 10
VL - 72
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2023_Li-Zhulanov,
author = {N. S. Li-Zhulanov and V A Kuznetsova and Yu.V Gatilov and K P Volcho and M V Khvostov and T G Tolstikova and N. F. Salakhutdinov},
title = {Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity},
journal = {Russian Chemical Bulletin},
year = {2023},
volume = {72},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1007/s11172-023-4044-2},
number = {10},
pages = {2430--2438},
doi = {10.1007/s11172-023-4044-2}
}
Cite this
MLA
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Li-Zhulanov, N. S., et al. “Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity.” Russian Chemical Bulletin, vol. 72, no. 10, Oct. 2023, pp. 2430-2438. https://doi.org/10.1007/s11172-023-4044-2.
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