volume 29 issue 4 pages 738-747

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

Publication typeJournal Article
Publication date2020-02-07
scimago Q2
wos Q3
SJR0.470
CiteScore5.1
Impact factor3.1
ISSN10542523, 15548120
Organic Chemistry
General Pharmacology, Toxicology and Pharmaceutics
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.
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Ilina I. et al. Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes // Medicinal Chemistry Research. 2020. Vol. 29. No. 4. pp. 738-747.
GOST all authors (up to 50) Copy
Ilina I., Morozova E., Pavlova A., Korchagina D., Tolstikova T., Volcho K. P., Salakhutdinov N. Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes // Medicinal Chemistry Research. 2020. Vol. 29. No. 4. pp. 738-747.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1007/s00044-020-02518-3
UR - https://doi.org/10.1007/s00044-020-02518-3
TI - Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes
T2 - Medicinal Chemistry Research
AU - Ilina, Irina
AU - Morozova, Ekaterina
AU - Pavlova, Alla
AU - Korchagina, Dina
AU - Tolstikova, Tatyana
AU - Volcho, Konstantin P.
AU - Salakhutdinov, Nariman
PY - 2020
DA - 2020/02/07
PB - Springer Nature
SP - 738-747
IS - 4
VL - 29
SN - 1054-2523
SN - 1554-8120
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Ilina,
author = {Irina Ilina and Ekaterina Morozova and Alla Pavlova and Dina Korchagina and Tatyana Tolstikova and Konstantin P. Volcho and Nariman Salakhutdinov},
title = {Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes},
journal = {Medicinal Chemistry Research},
year = {2020},
volume = {29},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007/s00044-020-02518-3},
number = {4},
pages = {738--747},
doi = {10.1007/s00044-020-02518-3}
}
MLA
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MLA Copy
Ilina, Irina, et al. “Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes.” Medicinal Chemistry Research, vol. 29, no. 4, Feb. 2020, pp. 738-747. https://doi.org/10.1007/s00044-020-02518-3.