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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 и др.

в: Medicinal Chemistry Research, Том 24, № 11, 28.11.2015, стр. 3821-3830.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

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, Том. 24, № 11, стр. 3821-3830. https://doi.org/10.1007/s00044-015-1426-5

APA

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/s00044-015-1426-5

Vancouver

Pavlova A, Mikhalchenko O, Rogachev A, Il'ina I, Korchagina D, Gatilov Y и др. 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 нояб. 28;24(11):3821-3830. doi: 10.1007/s00044-015-1426-5

Author

Pavlova, Alla ; Mikhalchenko, Oksana ; Rogachev, Artem и др. / 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. в: Medicinal Chemistry Research. 2015 ; Том 24, № 11. стр. 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 -

ID: 35391688