Synthesis and analgesic activity of octahydro-2H-chromenols, derivatives of aliphatic ketones

被引:8
作者
Il'ina, I. V. [1 ,2 ]
Korchagina, D. V. [1 ]
Morozova, E. A. [1 ]
Tolstikova, T. G. [1 ]
Volcho, K. P. [1 ,2 ]
Salakhutdinov, N. F. [1 ,2 ]
机构
[1] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Prosp Akad Lavrentieva, Novosibirsk 630090, Russia
[2] Novosibirsk Natl Res State Univ, 1 Ul Pirogova, Novosibirsk 630090, Russia
关键词
monoterpenoids; montmorillonite K10; heterocyclic compounds; analgesic activity; ISOPULEGOL; VANILLIN; ACIDITY;
D O I
10.1007/s11172-019-2520-5
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of compounds with a hydrogenated 2H-chromene skeleton was synthesized by the reaction of ketones and available para-menthane monoterpenoid ()-isopulegol. A condensation product of ()-isopulegol with the monoterpene ketone l-menthone was synthesized for the first time. The synthesized heterocycles were tested for analgesic activity and compounds with high analgesic activity in the in vivo tests were identified.
引用
收藏
页码:1061 / 1066
页数:6
相关论文
共 19 条
[1]   The First Synthesis of (4S,5R,6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid [J].
Ardashov, Oleg V. ;
Demidova, Yuliya S. ;
Korchagina, Dina V. ;
Volcho, Konstantin P. ;
Simakova, Irina L. ;
Salakhutdinov, Nariman F. .
HELVETICA CHIMICA ACTA, 2015, 98 (10) :1442-1455
[2]   An Environmentally Benign Synthesis of Octahydro-2H-chromen-4-ols via Modified Montmorillonite K10 Catalyzed Prins Cyclization Reaction [J].
Baishya, Gakul ;
Sarmah, Barnali ;
Hazarika, Nabajyoti .
SYNLETT, 2013, 24 (09) :1137-1141
[3]  
EDDY NB, 1953, J PHARMACOL EXP THER, V107, P385
[4]   Highly potent activity of isopulegol-derived substituted octahydro-2H-chromen-4-ols against influenza A and B viruses [J].
Ilyina, Irina, V ;
Zarubaev, Vladimir V. ;
Lavrentieva, Irina N. ;
Shtro, Anna A. ;
Esaulkova, Iana L. ;
Korchagina, Dina, V ;
Borisevich, Sophia S. ;
Volcho, Konstantin P. ;
Salakhutdinov, Nariman F. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (11) :2061-2067
[5]   Supramolecular Complex of Ibuprofen with Larch Polysaccharide Arabinogalactan: Studies on Bioavailability and Pharmacokinetics [J].
Khvostov, Mikhail V. ;
Borisov, Sergey A. ;
Tolstikova, Tatjana G. ;
Dushkin, Alexander V. ;
Tsyrenova, Biligma D. ;
Chistyachenko, Yulia S. ;
Polyakov, Nikolay E. ;
Dultseva, Galina G. ;
Onischuk, Andrey A. ;
An'kov, Sergey V. .
EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS, 2017, 42 (03) :431-440
[6]  
Kishore K. R., 2013, J BRAZIL CHEM SOC, V24, P1414, DOI [10.5935/0103-5053.20130178, DOI 10.5935/0103-5053.20130178]
[7]   Effect of chiral polyhydrochromenes on cannabinoid system [J].
Li-Zhulanov, Nikolai S. ;
Il'ina, Irina V. ;
Chicca, Andrea ;
Schenker, Patricia ;
Patrusheva, Oksana S. ;
Nazimova, Ekaterina V. ;
Korchagina, Dina V. ;
Krasavin, Mikhail ;
Volcho, Konstantin P. ;
Salakhutdinov, Nariman F. .
MEDICINAL CHEMISTRY RESEARCH, 2019, 28 (04) :450-464
[8]  
Moore N D., 2009, Acute pain, V11, P129, DOI [DOI 10.1016/J.ACPAIN.2009.09.003, 10.1016/j.acpain.2009.09.003]
[9]   Influenza Antiviral Activity of Br-Containing [2R,4R(S),4aR,7R,8aR]-4,7-Dimethyl-2-(Thiophen-2-YL)Octahydro-2H-Chromen-4-Ols Prepared from (-)-Isopulegol [J].
Nazimova, E. V. ;
Shtro, A. A. ;
Anikin, V. B. ;
Patrusheva, O. S. ;
Il'ina, I. V. ;
Korchagina, D. V. ;
Zarubaev, V. V. ;
Volcho, K. P. ;
Salakhutdinov, N. F. .
CHEMISTRY OF NATURAL COMPOUNDS, 2017, 53 (02) :260-264
[10]   Discovery of highly potent analgesic activity of isopulegol-derived (2R,4aR,7R,8aR)-4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol [J].
Nazimova, Ekaterina ;
Pavlova, Alla ;
Mikhalchenko, Oksana ;
Il'ina, Irina ;
Korchagina, Dina ;
Tolstikova, Tat'yana ;
Volcho, Konstantin ;
Salakhutdinov, Nariman .
MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (07) :1369-1383