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, Oksana Mikhalchenko, Artem Rogachev, Irina Il'ina, Dina Korchagina, Yuriy Gatilov, Tat'yana Tolstikova, Konstantin Volcho, Nariman Salakhutdinov

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

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.

Язык оригиналаанглийский
Страницы (с-по)3821-3830
Число страниц10
ЖурналMedicinal Chemistry Research
Том24
Номер выпуска11
DOI
СостояниеОпубликовано - 28 ноя 2015

Предметные области OECD FOS+WOS

  • 3.01 ФУНДАМЕНТАЛЬНАЯ МЕДИЦИНА
  • 1.04 ХИМИЧЕСКИЕ НАУКИ

ГРНТИ

  • 31 ХИМИЯ

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