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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. / Pavlova, Alla; Mikhalchenko, Oksana; Rogachev, Artem et al.
In:
Medicinal Chemistry Research, Vol. 24, No. 11, 28.11.2015, p. 3821-3830.
Research output: Contribution to journal › Article › peer-review
Harvard
Pavlova, A, Mikhalchenko, O
, Rogachev, A, Il'ina, I, Korchagina, D, Gatilov, Y, Tolstikova, T, Volcho, K
& Salakhutdinov, N 2015, '
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, pp. 3821-3830.
https://doi.org/10.1007/s00044-015-1426-5APA
Pavlova, A., Mikhalchenko, O.
, Rogachev, A., Il'ina, I., Korchagina, D., Gatilov, Y., Tolstikova, T., Volcho, K.
, & Salakhutdinov, N. (2015).
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,
24(11), 3821-3830.
https://doi.org/10.1007/s00044-015-1426-5Vancouver
Pavlova A, Mikhalchenko O
, Rogachev A, Il'ina I, Korchagina D, Gatilov Y 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 Nov 28;24(11):3821-3830. doi: 10.1007/s00044-015-1426-5
Author
Pavlova, Alla ; Mikhalchenko, Oksana
; Rogachev, Artem 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. In:
Medicinal Chemistry Research. 2015 ; Vol. 24, No. 11. pp. 3821-3830.
BibTeX
@article{8b25bdc90a154e0390bcfb560ce48f67,
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",
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 (-)-alpha-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.",
keywords = "Terpene, Chromene, Heterocyclic compounds, Analgesic activity, Acetic acid-induced writhing test, Hot plate test, Stereoisomers, MONTMORILLONITE CLAY, VERBENOL EPOXIDE, ALDEHYDES",
author = "Alla Pavlova and Oksana Mikhalchenko and Artem Rogachev and Irina Il'ina and Dina Korchagina and Yuriy Gatilov and Tat'yana Tolstikova and Konstantin Volcho and Nariman Salakhutdinov",
note = "Funding Information: Authors are grateful to the Russian Foundation for Basic Research (Grant No 13-03-00206a) for the financial support. Publisher Copyright: {\textcopyright} 2015 Springer Science+Business Media New York.",
year = "2015",
month = nov,
day = "28",
doi = "10.1007/s00044-015-1426-5",
language = "English",
volume = "24",
pages = "3821--3830",
journal = "Medicinal Chemistry Research",
issn = "1054-2523",
publisher = "Springer Nature",
number = "11",
}
RIS
TY - JOUR
T1 - 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
AU - Pavlova, Alla
AU - Mikhalchenko, Oksana
AU - Rogachev, Artem
AU - Il'ina, Irina
AU - Korchagina, Dina
AU - Gatilov, Yuriy
AU - Tolstikova, Tat'yana
AU - Volcho, Konstantin
AU - Salakhutdinov, Nariman
N1 - Funding Information:
Authors are grateful to the Russian Foundation for Basic Research (Grant No 13-03-00206a) for the financial support.
Publisher Copyright:
© 2015 Springer Science+Business Media New York.
PY - 2015/11/28
Y1 - 2015/11/28
N2 - 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 (-)-alpha-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.
AB - 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 (-)-alpha-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.
KW - Terpene
KW - Chromene
KW - Heterocyclic compounds
KW - Analgesic activity
KW - Acetic acid-induced writhing test
KW - Hot plate test
KW - Stereoisomers
KW - MONTMORILLONITE CLAY
KW - VERBENOL EPOXIDE
KW - ALDEHYDES
UR - http://www.scopus.com/inward/record.url?scp=84942503083&partnerID=8YFLogxK
UR - https://www.elibrary.ru/item.asp?id=24952964
U2 - 10.1007/s00044-015-1426-5
DO - 10.1007/s00044-015-1426-5
M3 - Article
VL - 24
SP - 3821
EP - 3830
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
SN - 1054-2523
IS - 11
ER -
