Synthesis and analgesic activity of monoterpenoid-derived alkyl-substituted chiral hexahydro-2H-chromenes

Irina Il’ina; Alla Pavlova; Dina Korchagina; Oleg Ardashov; Tat’yana Tolstikova; Konstantin Volcho; Nariman Salakhutdinov

doi:10.1007/s00044-017-1847-4

Synthesis and analgesic activity of monoterpenoid-derived alkyl-substituted chiral hexahydro-2H-chromenes

Irina Il’ina, Alla Pavlova, Dina Korchagina, Oleg Ardashov, Tat’yana Tolstikova, Konstantin Volcho, Nariman Salakhutdinov

Кафедра органической химии ФЕН

Результат исследования: Научные публикации в периодических изданиях › статья › рецензирование

6 Цитирования (Scopus)

Аннотация

A set of new 2-alkyl-substituted 4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols was obtained by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic aldehydes in the presence of montmorillonite clay K10. Synthesized compounds were evaluated for their analgesic activity in vivo using the acetic acid-induced writhing test and the hot-plate test. Five compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two of them also demonstrated analgesic activity in the hot-plate test. These compounds seem to be most promising for further development.

Язык оригинала	английский
Страницы (с-по)	1415-1426
Число страниц	12
Журнал	Medicinal Chemistry Research
Том	26
Номер выпуска	7
DOI	https://doi.org/10.1007/s00044-017-1847-4
Состояние	Опубликовано - 1 июл. 2017

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10.1007/s00044-017-1847-4

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title = "Synthesis and analgesic activity of monoterpenoid-derived alkyl-substituted chiral hexahydro-2H-chromenes",

abstract = "A set of new 2-alkyl-substituted 4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols was obtained by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic aldehydes in the presence of montmorillonite clay K10. Synthesized compounds were evaluated for their analgesic activity in vivo using the acetic acid-induced writhing test and the hot-plate test. Five compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two of them also demonstrated analgesic activity in the hot-plate test. These compounds seem to be most promising for further development.",

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Synthesis and analgesic activity of monoterpenoid-derived alkyl-substituted chiral hexahydro-2H-chromenes. / Il’ina, Irina; Pavlova, Alla; Korchagina, Dina и др.

В: Medicinal Chemistry Research, Том 26, № 7, 01.07.2017, стр. 1415-1426.

Результат исследования: Научные публикации в периодических изданиях › статья › рецензирование

TY - JOUR

T1 - Synthesis and analgesic activity of monoterpenoid-derived alkyl-substituted chiral hexahydro-2H-chromenes

AU - Il’ina, Irina

AU - Pavlova, Alla

AU - Korchagina, Dina

AU - Ardashov, Oleg

AU - Tolstikova, Tat’yana

AU - Volcho, Konstantin

AU - Salakhutdinov, Nariman

PY - 2017/7/1

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N2 - A set of new 2-alkyl-substituted 4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols was obtained by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic aldehydes in the presence of montmorillonite clay K10. Synthesized compounds were evaluated for their analgesic activity in vivo using the acetic acid-induced writhing test and the hot-plate test. Five compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two of them also demonstrated analgesic activity in the hot-plate test. These compounds seem to be most promising for further development.

AB - A set of new 2-alkyl-substituted 4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols was obtained by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic aldehydes in the presence of montmorillonite clay K10. Synthesized compounds were evaluated for their analgesic activity in vivo using the acetic acid-induced writhing test and the hot-plate test. Five compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two of them also demonstrated analgesic activity in the hot-plate test. These compounds seem to be most promising for further development.

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KW - Analgesic activity

KW - Chromene

KW - Heterocyclic compounds

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KW - Terpene

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