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Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes. / Il’ina, Irina; Morozova, Ekaterina; Pavlova, Alla et al.

In: Medicinal Chemistry Research, Vol. 29, No. 4, 01.04.2020, p. 738-747.

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

Harvard

Il’ina, I, Morozova, E, Pavlova, A, Korchagina, D, Tolstikova, T, Volcho, K & Salakhutdinov, N 2020, 'Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes', Medicinal Chemistry Research, vol. 29, no. 4, pp. 738-747. https://doi.org/10.1007/s00044-020-02518-3

APA

Il’ina, I., Morozova, E., Pavlova, A., Korchagina, D., Tolstikova, T., Volcho, K., & Salakhutdinov, N. (2020). Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes. Medicinal Chemistry Research, 29(4), 738-747. https://doi.org/10.1007/s00044-020-02518-3

Vancouver

Il’ina I, Morozova E, Pavlova A, Korchagina D, Tolstikova T, Volcho K et al. Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes. Medicinal Chemistry Research. 2020 Apr 1;29(4):738-747. doi: 10.1007/s00044-020-02518-3

Author

Il’ina, Irina ; Morozova, Ekaterina ; Pavlova, Alla et al. / Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes. In: Medicinal Chemistry Research. 2020 ; Vol. 29, No. 4. pp. 738-747.

BibTeX

@article{7ec3c3bf33e547c4b20f9be17b5679ff,
title = "Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes",
abstract = "New hexahydro-2H-chromenes were synthesized by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic ketones in the presence of montmorillonite clay H+-K10. The compounds formed and isolated as a pair of diastereoisomers were evaluated for their analgesic activity in vivo. It was found that the analgesic activity of (4aR,8R,8aR)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydrospiro[chromene-2,1ʹ-cyclohexane]-4,8-diol 8b significantly exceeds (two orders of magnitude higher) the activity of diclofenac sodium in the acetic acid-induced writhing test. It has low acute toxicity and is very promising for further development.",
keywords = "Acetic acid-induced writhing test, Analgesic activity, Chromene, Heterocyclic compounds, Hot plate test, Terpene, METHOXY GROUPS, HYDROXY, NATURAL-PRODUCTS",
author = "Irina Il{\textquoteright}ina and Ekaterina Morozova and Alla Pavlova and Dina Korchagina and Tat{\textquoteright}yana Tolstikova and Konstantin Volcho and Nariman Salakhutdinov",
year = "2020",
month = apr,
day = "1",
doi = "10.1007/s00044-020-02518-3",
language = "English",
volume = "29",
pages = "738--747",
journal = "Medicinal Chemistry Research",
issn = "1054-2523",
publisher = "Springer Nature",
number = "4",

}

RIS

TY - JOUR

T1 - Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes

AU - Il’ina, Irina

AU - Morozova, Ekaterina

AU - Pavlova, Alla

AU - Korchagina, Dina

AU - Tolstikova, Tat’yana

AU - Volcho, Konstantin

AU - Salakhutdinov, Nariman

PY - 2020/4/1

Y1 - 2020/4/1

N2 - New hexahydro-2H-chromenes were synthesized by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic ketones in the presence of montmorillonite clay H+-K10. The compounds formed and isolated as a pair of diastereoisomers were evaluated for their analgesic activity in vivo. It was found that the analgesic activity of (4aR,8R,8aR)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydrospiro[chromene-2,1ʹ-cyclohexane]-4,8-diol 8b significantly exceeds (two orders of magnitude higher) the activity of diclofenac sodium in the acetic acid-induced writhing test. It has low acute toxicity and is very promising for further development.

AB - New hexahydro-2H-chromenes were synthesized by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic ketones in the presence of montmorillonite clay H+-K10. The compounds formed and isolated as a pair of diastereoisomers were evaluated for their analgesic activity in vivo. It was found that the analgesic activity of (4aR,8R,8aR)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydrospiro[chromene-2,1ʹ-cyclohexane]-4,8-diol 8b significantly exceeds (two orders of magnitude higher) the activity of diclofenac sodium in the acetic acid-induced writhing test. It has low acute toxicity and is very promising for further development.

KW - Acetic acid-induced writhing test

KW - Analgesic activity

KW - Chromene

KW - Heterocyclic compounds

KW - Hot plate test

KW - Terpene

KW - METHOXY GROUPS

KW - HYDROXY

KW - NATURAL-PRODUCTS

UR - http://www.scopus.com/inward/record.url?scp=85079194094&partnerID=8YFLogxK

U2 - 10.1007/s00044-020-02518-3

DO - 10.1007/s00044-020-02518-3

M3 - Article

AN - SCOPUS:85079194094

VL - 29

SP - 738

EP - 747

JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

SN - 1054-2523

IS - 4

ER -

ID: 23428272