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Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity. / Li-Zhulanov, N. S.; Kuznetsova, V. A.; Gatilov, Yu V. et al.

In: Russian Chemical Bulletin, Vol. 72, No. 10, 10.2023, p. 2430-2438.

Research output: Contribution to journal › Article › peer-review

Harvard

Li-Zhulanov, NS, Kuznetsova, VA, Gatilov, YV, Volcho, KP, Khvostov, MV, Tolstikova, TG & Salakhutdinov, NF 2023, 'Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity', Russian Chemical Bulletin, vol. 72, no. 10, pp. 2430-2438. https://doi.org/10.1007/s11172-023-4044-2

APA

Li-Zhulanov, N. S., Kuznetsova, V. A., Gatilov, Y. V., Volcho, K. P., Khvostov, M. V., Tolstikova, T. G., & Salakhutdinov, N. F. (2023). Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity. Russian Chemical Bulletin, 72(10), 2430-2438. https://doi.org/10.1007/s11172-023-4044-2

Vancouver

Li-Zhulanov NS, Kuznetsova VA, Gatilov YV, Volcho KP, Khvostov MV, Tolstikova TG et al. Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity. Russian Chemical Bulletin. 2023 Oct;72(10):2430-2438. doi: 10.1007/s11172-023-4044-2

Author

Li-Zhulanov, N. S. ; Kuznetsova, V. A. ; Gatilov, Yu V. et al. / Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity. In: Russian Chemical Bulletin. 2023 ; Vol. 72, No. 10. pp. 2430-2438.

BibTeX

@article{dff431c2ab53424f80b50bdf41896831,
title = "Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity",
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.",
keywords = "Prins—Ritter reaction, dopamine receptors, isopulegol, spirocyclic compounds",
author = "Li-Zhulanov, {N. S.} and Kuznetsova, {V. A.} and Gatilov, {Yu V.} and Volcho, {K. P.} and Khvostov, {M. V.} and Tolstikova, {T. G.} and Salakhutdinov, {N. F.}",
note = "The authors are grateful to the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences, for spectral and analytical measurements. Публикация для корректировки.",
year = "2023",
month = oct,
doi = "10.1007/s11172-023-4044-2",
language = "English",
volume = "72",
pages = "2430--2438",
journal = "Russian Chemical Bulletin",
issn = "1066-5285",
publisher = "Springer Nature",
number = "10",

}

RIS

TY - JOUR

T1 - Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity

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.

N1 - The authors are grateful to the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences, for spectral and analytical measurements. Публикация для корректировки.

PY - 2023/10

Y1 - 2023/10

N2 - 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.

AB - 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.

KW - Prins—Ritter reaction

KW - dopamine receptors

KW - isopulegol

KW - spirocyclic compounds

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85176244571&origin=inward&txGid=d967017e6acb611b556661ba03b00a52

UR - https://www.mendeley.com/catalogue/5daa44e5-daf2-3dc8-868a-df504c0dfb24/

U2 - 10.1007/s11172-023-4044-2

DO - 10.1007/s11172-023-4044-2

M3 - Article

VL - 72

SP - 2430

EP - 2438

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 10

ER -

ID: 59548130