Synthesis and analgesic activity of aliphatic ketones-derived chiral hexahydro-2H-chromenes

被引：4
作者：
Il'ina, Irina [1 ]
Morozova, Ekaterina [1 ]
Pavlova, Alla [1 ]
Korchagina, Dina [1 ]
Tolstikova, Tat'yana [1 ]
Volcho, Konstantin [1 ,2 ]
Salakhutdinov, Nariman [1 ,2 ]
机构：
[1] Russian Acad Sci, Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentjev Av 9, Novosibirsk 630090, Russia
[2] Novosibirsk State Univ, Pirogova St 1, Novosibirsk 630090, Russia
来源：
MEDICINAL CHEMISTRY RESEARCH | 2020年 / 29卷 / 04期
关键词：
Terpene; Chromene; Heterocyclic compounds; Analgesic activity; Acetic acid-induced writhing test; Hot plate test; NATURAL-PRODUCTS; METHOXY GROUPS; HYDROXY;
D O I：
10.1007/s00044-020-02518-3
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
New hexahydro-2H-chromenes were synthesized by reactions of monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aliphatic ketones in the presence of montmorillonite clay H+-K10. The compounds formed and isolated as a pair of diastereoisomers were evaluated for their analgesic activity in vivo. It was found that the analgesic activity of (4aR,8R,8aR)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydrospiro[chromene-2,1MODIFIER LETTER PRIME-cyclohexane]-4,8-diol 8b significantly exceeds (two orders of magnitude higher) the activity of diclofenac sodium in the acetic acid-induced writhing test. It has low acute toxicity and is very promising for further development.
引用
收藏
页码：738 / 747
页数：10
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