Synthesis and Analgesic Activity of Monoterpenoid Aldehyde-derived Hydro-2H-chromeneols

Synthesis and Analgesic Activity of Monoterpenoid Aldehyde-derived Hydro-2H-chromeneols Научная публикация

Журнал

Letters in Drug Design and Discovery
ISSN: 1570-1808 , E-ISSN: 1875-628X

Вых. Данные

Год: 2020, Том: 17, Номер: 1, Страницы: 68-78 Страниц : 11 DOI: 10.2174/1570180816666181114131220

Ключевые слова

Monoterpenoid aldehyde; isopulegol; chromene; analgesia; acetic acid-induced writhing test; hot-plate test

Авторы

Il'ina Irina ^1,2 , Morozova Ekaterina ¹ , Korchagina Dina ¹ , Volcho Konstantin ^1,2 , Tolstikova Tat'yana ¹ , Salakhutdinov Nariman ^1,2

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Lavrentjev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia

Background: Despite a variety of drugs used to stop acute pain, problems related to their insufficient efficacy and undesirable side effects have remained unresolved. Therefore, the search for analgesics of new structural types, which combine high activity with low toxicity, is a topical issue. It is known that a number of compounds with a hydrogenated 2H-chromene skeleton exhibit significant analgesic activity in in vivo tests. Methods: New hydro-2H-chromenols containing monoterpenoid moieties were obtained via one-pot synthesis by the interaction between para-menthane alcohols and commercially available monoterpene aldehydes: Citral, hydroxycitronellal, myrtenal, and perillaldehyde. The analgesic activity of these compounds was studied in the acetic acid-induced writhing test and hot plate test. Results: The target compounds were characterized using NMR and HR-MS. Most of them exhibited pronounced analgesic activity. Conclusion: Due to high analgesic activity, (2S,4aR,8R,8aR)-2-((E)-2,6-dimethylhepta-1, 5-dien-1-yl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H- chromene-4,8-diol is considered as candidate compound to participate in further research.

Il'ina I. , Morozova E. , Korchagina D. , Volcho K. , Tolstikova T. , Salakhutdinov N.
Synthesis and Analgesic Activity of Monoterpenoid Aldehyde-derived Hydro-2H-chromeneols
Letters in Drug Design and Discovery. 2020. V.17. N1. P.68-78. DOI: 10.2174/1570180816666181114131220 WOS Scopus

Опубликована в печати:

31 дек. 2019 г.

Web of science	WOS:000505045400008
Scopus	2-s2.0-85078714444
OpenAlex	W2900739933