Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers

被引：18
作者：
Anikina, Lada V. [1 ]
Vikharev, Yuri B. [1 ]
Baranov, Vladimir V. [2 ]
Malyshev, Oleg R. [2 ]
Kravchenko, Angelina N. [2 ]
机构：
[1] Russian Acad Sci, Inst Physiol Act Cpds, Chernogolovka 142432, Moscow Region, Russia
[2] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
来源：
MENDELEEV COMMUNICATIONS | 2018年 / 28卷 / 03期
基金：
俄罗斯科学基金会;
关键词：
OPEN-FIELD TEST; SELF-ORGANIZATION; MICE; 5-HYDROXYTRYPTOPHAN; GLYCOLURILS; THALIDOMIDE; DRUGS; ACID;
D O I：
10.1016/j.mencom.2018.05.030
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Racemic Albicar (2,6-diethyl-4,8-dimethylglycoluril) has been synthesized and resolved into enantiomers on a preparative scale by chiral HPLC. A comparison of the pharmacological effects of these compounds has been performed for the first time. It has been demonstrated that the (-)-(1S,5S)-enantiomer exerts a stimulating effect on the central nervous system due to activation of the serotonergic system, since it potentiates the effects of 5-hydroxytryptophan (the serotonin precursor), while the antagonist of serotonin receptors blocks its activity; the (+)-(1R,5R)-enantiomer evinces an inhibitory effect.
引用
收藏
页码：317 / 319
页数：3
相关论文
共 39 条
  • [1] Studies of the Hydrolytic Stability of the Biologically Active Substance Bicaret
    Berlyand, A. S.
    Prokopov, A. A.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2014, 48 (05) : 347 - 349
  • [2] Chemico-Pharmaceutical Analysis of the Biologically Active Substances Albicar
    Berlyand, A. S.
    Lebedev, O. V.
    Prokopov, A. A.
    [J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2013, 47 (03) : 176 - 178
  • [3] BERLYAND AS, 2013, KHIM FARM ZH, V47, P52
  • [4] BERLYAND AS, 2014, KHIM FARM ZH, V48, P47
  • [5] Bossier I.R., 1964, THERAPIE, V19, P571
  • [6] The anxiolytic-like effect of 6-styryl-2-pyrone in mice involves GABAergic mechanism of action
    Camelo Chaves, Edna Maria
    Honorio-Junior, Jose Eduardo Ribeiro
    Soares Sousa, Caren Nadia
    Monteiro, Valdecio Silveira
    Tenorio Nonato, Dayanne Terra
    Dantas, Leonardo Pimentel
    Suassuna Carneiro Lucio, Ana Silvia
    Barbosa-Filho, Jose Maria
    Azevedo Patrocinio, Manoel Claudio
    Barros Viana, Glauce Socorro
    Mendes Vasconcelos, Silvania Maria .
    [J]. METABOLIC BRAIN DISEASE, 2018, 33 (01) : 139 - 149
  • [7] Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide
    Chen, Jianbin
    Natte, Kishore
    Spannenberg, Anke
    Neumann, Helfried
    Beller, Matthias
    Wu, Xiao-Feng
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (30) : 5578 - 5581
  • [8] The Flavonoid Glycosides, Myricitrin, Gossypin and Naringin Exert Anxiolytic Action in Mice
    Fernandez, Sebastian P.
    Nguyen, Michael
    Yow, Tin Thing
    Chu, Cindy
    Johnston, Graham A. R.
    Hanrahan, Jane R.
    Chebib, Mary
    [J]. NEUROCHEMICAL RESEARCH, 2009, 34 (10) : 1867 - 1875
  • [9] Crystal structure, IR and 1H NMR spectra of tetranitratobis μ-(2,4,6,8-tetraethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione-O,O′)]diethanolodicadmium
    Gazieva, G. A.
    Golovanov, D. G.
    Lozhkin, P. V.
    Lysenko, K. A.
    Kravchenko, A. N.
    [J]. RUSSIAN JOURNAL OF INORGANIC CHEMISTRY, 2007, 52 (09) : 1441 - 1445
  • [10] 4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxyalkyl-, N-hydroxyalkyl-, and N-(aminoalkyl)ureas 4. α-Ureidoalkylation of N-(2-acetylaminoethyl)ureas
    Gazieva, G. A.
    Lozhkin, P. V.
    Baranov, V. V.
    Kravchenko, A. N.
    Makhova, N. N.
    [J]. RUSSIAN CHEMICAL BULLETIN, 2010, 59 (03) : 642 - 646
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