Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol
Ekaterina Nazimova
1, 2
,
Alla Pavlova
1
,
Oksana Mikhalchenko
1
,
Irina Ilina
1, 2
,
Dina Korchagina
1
,
Tatyana Tolstikova
1
,
Konstantin Volcho
1, 2
,
Publication type: Journal Article
Publication date: 2016-04-18
scimago Q2
wos Q3
SJR: 0.470
CiteScore: 5.1
Impact factor: 3.1
ISSN: 10542523, 15548120
Organic Chemistry
General Pharmacology, Toxicology and Pharmaceutics
Abstract
A large set of chiral heterocyclic compounds with the octahydro-2H-chromene scaffold was first obtained by a reaction of (−)-isopulegol and (+)-neoisopulegol with furan-2-carbaldehyde, thiophene-2-carbaldehyde and their derivatives and isomers in the presence of montmorillonite K10 clay. Most of the (−)-isopulegol-derived compounds exhibited a significant analgesic activity in the acetic acid-induced writhing test. Compound 3b obtained by a reaction of (−)-isopulegol with thiophene-2-carbaldehyde demonstrated a significant analgesic effect in this test within 15 min after oral administration at the dose of 1 mg/kg and retains the effect for at least 24 h. Compound 3b exhibited analgesic activity in the hot plate test also. A change in the sulfur atom position in the aromatic ring was found to lead to the effect reversal in the hot plate test.
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Nazimova E. et al. Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol // Medicinal Chemistry Research. 2016. Vol. 25. No. 7. pp. 1369-1383.
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Nazimova E., Pavlova A., Mikhalchenko O., Ilina I., Korchagina D., Tolstikova T., Volcho K., Salakhutdinov N. Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol // Medicinal Chemistry Research. 2016. Vol. 25. No. 7. pp. 1369-1383.
Cite this
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TY - JOUR
DO - 10.1007/s00044-016-1573-3
UR - https://doi.org/10.1007/s00044-016-1573-3
TI - Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol
T2 - Medicinal Chemistry Research
AU - Nazimova, Ekaterina
AU - Pavlova, Alla
AU - Mikhalchenko, Oksana
AU - Ilina, Irina
AU - Korchagina, Dina
AU - Tolstikova, Tatyana
AU - Volcho, Konstantin
AU - Salakhutdinov, Nariman
PY - 2016
DA - 2016/04/18
PB - Springer Nature
SP - 1369-1383
IS - 7
VL - 25
SN - 1054-2523
SN - 1554-8120
ER -
Cite this
BibTex (up to 50 authors)
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@article{2016_Nazimova,
author = {Ekaterina Nazimova and Alla Pavlova and Oksana Mikhalchenko and Irina Ilina and Dina Korchagina and Tatyana Tolstikova and Konstantin Volcho and Nariman Salakhutdinov},
title = {Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol},
journal = {Medicinal Chemistry Research},
year = {2016},
volume = {25},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s00044-016-1573-3},
number = {7},
pages = {1369--1383},
doi = {10.1007/s00044-016-1573-3}
}
Cite this
MLA
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Nazimova, Ekaterina, et al. “Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol.” Medicinal Chemistry Research, vol. 25, no. 7, Apr. 2016, pp. 1369-1383. https://doi.org/10.1007/s00044-016-1573-3.