Sciact
  • EN
  • RU

Highly potent analgesic activity of monoterpene-derived (2S,4aR,8R,8aR)-2-aryl-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols Full article

Journal Medicinal Chemistry Research
ISSN: 1054-2523 , E-ISSN: 1554-8120
Output data Year: 2014, Volume: 23, Number: 12, Pages: 5063-5073 Pages count : DOI: 10.1007/s00044-014-1071-4
Tags Terpene; Chromene; Heterocyclic compounds; Analgesic activity; Acetic acid-induced writhing test; Hot-plate test
Authors Il'ina Irina 1 , Mikhalchenko Oksana 1 , Pavlova Alla 1 , Korchagina Dina 1 , Tolstikova Tat'yana 1 , Volcho Konstantin 1 , Salakhutdinov Nariman 1,2 , Pokushalov Evgeniy 3
Affiliations
1 (Данные Web of science) Russian Acad Sci, Novosibirsk Organ Chem Inst, Siberian Branch, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia
3 (Данные Web of science) State Res Inst Circulat Pathol, Novosibirsk 630055, Russia

Abstract: New chiral heterocyclic compounds with a hexahydro-2H-chromene framework were synthesized by reactions of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes in the presence of montmorillonite clay. The analgesic activity of the compounds was studied in vivo. The majority of these compounds showed significant analgesic activity in the acetic acid-induced writhing test; the compounds containing one hydroxy and one methoxy substituents also showed analgesic activity in the hot-plate test. (2S,4aR,8R,8aR)-2-(3-Hydroxy-4-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diol was as effective as the diclofenac sodium reference taken in the same dose in both tests. It has low acute toxicity and is very promising for further development.
Cite: Il'ina I. , Mikhalchenko O. , Pavlova A. , Korchagina D. , Tolstikova T. , Volcho K. , Salakhutdinov N. , Pokushalov E.
Highly potent analgesic activity of monoterpene-derived (2S,4aR,8R,8aR)-2-aryl-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
Medicinal Chemistry Research. 2014. V.23. N12. P.5063-5073. DOI: 10.1007/s00044-014-1071-4 WOS Scopus РИНЦ
Dates:
Published online: Jun 26, 2014
Published print: Dec 1, 2014
Identifiers:
Web of science WOS:000344165100006
Scopus 2-s2.0-84911499505
Elibrary 24944206
OpenAlex W2027380442
Altmetrics: