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

被引：25

作者：

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
]}

机构：

[1] Russian Acad Sci, Novosibirsk Organ Chem Inst, Siberian Branch, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Novosibirsk 630090, Russia

[3] State Res Inst Circulat Pathol, Novosibirsk 630055, Russia

来源：

MEDICINAL CHEMISTRY RESEARCH | 2014年 / 23卷 / 12期

基金：

俄罗斯基础研究基金会;

关键词：

Terpene; Chromene; Heterocyclic compounds; Analgesic activity; Acetic acid-induced writhing test; Hot-plate test; MONTMORILLONITE CLAY; AROMATIC-ALDEHYDES; NATURAL-PRODUCTS; DRUG DISCOVERY; CANNABINOIDS; TRANSFORMATIONS; TERPENOIDS; MECHANISMS; EPOXIDE; DISEASE;

D O I：

10.1007/s00044-014-1071-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：5063 / 5073

页数：11

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