Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson's Disease

被引:68
作者
Ardashov, Oleg V. [1 ]
Pavlova, Alla V. [1 ]
Il'ina, Irina V. [1 ]
Morozova, Ekaterina A. [1 ]
Korchagina, Dina V. [1 ]
Karpova, Elena V. [1 ]
Volcho, Konstantin P. [1 ]
Tolstikova, Tat'yana G. [1 ]
Salakhutdinov, Nariman F. [1 ]
机构
[1] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
关键词
NEUROLEPTIC-INDUCED CATALEPSY; SECONDARY ALCOHOLS; MICE; OXIDATION; VERBENONE; RECEPTORS; EPOXIDE; KETONES; MPTP;
D O I
10.1021/jm2001579
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
(1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 possesses potent antiparkinsonian activity in both MPTP and haloperidol animal models. The use of compound 1 resulted in nearly full recovery of the locomotor and exploratory activities and was as effective as the comparator agent (levodopa). All eight stereoisomers of compound 1 have been synthesized and the influence of the absolute configuration on the antiparkinsonian activity of compound 1 was shown.
引用
收藏
页码:3866 / 3874
页数:9
相关论文
共 42 条
[1]  
ANELLI PL, 1987, J ORG CHEM, V52, P2559
[2]   Unusual products of the reactions of verbenone and verbenol with N-bromosuccinimide in the presence of water [J].
Ardashov, O. V. ;
Il'ina, I. V. ;
Korchagina, D. V. ;
Volcho, K. P. ;
Salakhutdinov, N. F. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (10) :1452-1455
[3]  
Ardashov OV, 2011, LETT DRUG DES DISCOV, V8, P375
[4]   Unusual α-hydroxyaldehyde with a cyclopentane framework from verbenol epoxide [J].
Ardashov, Olleg V. ;
Il'ina, Irina V. ;
Korchagina, Dina V. ;
Volcho, Konstantin P. ;
Salakhutdinov, Nariman F. .
MENDELEEV COMMUNICATIONS, 2007, 17 (05) :303-305
[5]   A SYNTHESIS OF VITAMIN-A FROM CYCLOHEXANONE [J].
ATTENBURROW, J ;
CAMERON, AFB ;
CHAPMAN, JH ;
EVANS, RM ;
HEMS, BA ;
JANSEN, ABA ;
WALKER, T .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :1094-1111
[6]   SYNTHETIC STUDIES TOWARDS FORSKOLIN [J].
BARALDI, PG ;
BARCO, A ;
BENETTI, S ;
FERRETTI, V ;
POLLINI, GP ;
POLO, E ;
ZANIRATO, V .
TETRAHEDRON, 1989, 45 (05) :1517-1532
[7]   Parkinson's disease: The syndrome, the pathogenesis and pathophysiology [J].
Bartels, Anna L. ;
Leenders, Klaus L. .
CORTEX, 2009, 45 (08) :915-921
[8]  
Bishop R., 1998, ORG SYNTH, V9, P692
[9]   Stereospecific synthesis of a novel azetido[2,1-c][1,4]-benzodiazepine (ABD) ring system with DNA recognition potential [J].
Bose, DS ;
Srinivas, P ;
Gurjar, MK .
TETRAHEDRON LETTERS, 1997, 38 (33) :5839-5842
[10]   INTRAMOLECULAR CONDENSATION OF STEROIDAL 17-ALPHA-FORMYL 17-BETA-ACETATES - MODEL STUDIES ON 19-NORSTEROIDS, AND A ROUTE TO 3-METHOXY-19-NOR-17-ALPHA-PREGNA-1,3,5(10)-TRIENE-21,17-CARBOLACTONE [J].
BULL, JR ;
STEER, LM .
TETRAHEDRON, 1990, 46 (15) :5389-5400