Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
Alla Pavlova
1
,
Oksana Mikhalchenko
1
,
Artem Rogachev
1, 2
,
Irina Ilina
1, 2
,
Dina Korchagina
1
,
Yuriy Gatilov
1, 2
,
Tatyana Tolstikova
1
,
Konstantin Volcho
1, 2
,
Publication type: Journal Article
Publication date: 2015-08-15
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
2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (−)-α-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.
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GOST
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Pavlova A. et al. Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols // Medicinal Chemistry Research. 2015. Vol. 24. No. 11. pp. 3821-3830.
GOST all authors (up to 50)
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Pavlova A., Mikhalchenko O., Rogachev A., Ilina I., Korchagina D., Gatilov Y., Tolstikova T., Volcho K., Salakhutdinov N. Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols // Medicinal Chemistry Research. 2015. Vol. 24. No. 11. pp. 3821-3830.
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RIS
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TY - JOUR
DO - 10.1007/s00044-015-1426-5
UR - https://doi.org/10.1007/s00044-015-1426-5
TI - Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
T2 - Medicinal Chemistry Research
AU - Pavlova, Alla
AU - Mikhalchenko, Oksana
AU - Rogachev, Artem
AU - Ilina, Irina
AU - Korchagina, Dina
AU - Gatilov, Yuriy
AU - Tolstikova, Tatyana
AU - Volcho, Konstantin
AU - Salakhutdinov, Nariman
PY - 2015
DA - 2015/08/15
PB - Springer Nature
SP - 3821-3830
IS - 11
VL - 24
SN - 1054-2523
SN - 1554-8120
ER -
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@article{2015_Pavlova,
author = {Alla Pavlova and Oksana Mikhalchenko and Artem Rogachev and Irina Ilina and Dina Korchagina and Yuriy Gatilov and Tatyana Tolstikova and Konstantin Volcho and Nariman Salakhutdinov},
title = {Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols},
journal = {Medicinal Chemistry Research},
year = {2015},
volume = {24},
publisher = {Springer Nature},
month = {aug},
url = {https://doi.org/10.1007/s00044-015-1426-5},
number = {11},
pages = {3821--3830},
doi = {10.1007/s00044-015-1426-5}
}
Cite this
MLA
Copy
Pavlova, Alla, et al. “Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols.” Medicinal Chemistry Research, vol. 24, no. 11, Aug. 2015, pp. 3821-3830. https://doi.org/10.1007/s00044-015-1426-5.