Home / Publications / Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers

Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers

Lada Vladimirovna Anikina 1
Lada Vladimirovna Anikina
, 
Yurii Borisovich Vikharev 1
Yurii Borisovich Vikharev
, 
Vladimir Vladimirovich Baranov 2
Vladimir Vladimirovich Baranov
, 
Oleg Robertovich Malyshev 2
Oleg Robertovich Malyshev
, 
Angelina Nikolaevna Kravchenko 2
Angelina Nikolaevna Kravchenko
10.1016/j.mencom.2018.05.030
Published 2018-04-27
Communication , Volume 28, Issue 3, 317-319
23
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Anikina L. V. et al. Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 317-319.
GOST all authors (up to 50) Copy
Anikina L. V., Vikharev Y. B., Baranov V. V., Malyshev O. R., Kravchenko A. N. Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 317-319.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.05.030
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.030
TI - Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers
T2 - Mendeleev Communications
AU - Anikina, Lada Vladimirovna
AU - Vikharev, Yurii Borisovich
AU - Baranov, Vladimir Vladimirovich
AU - Malyshev, Oleg Robertovich
AU - Kravchenko, Angelina Nikolaevna
PY - 2018
DA - 2018/04/27
PB - Mendeleev Communications
SP - 317-319
IS - 3
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Anikina,
author = {Lada Vladimirovna Anikina and Yurii Borisovich Vikharev and Vladimir Vladimirovich Baranov and Oleg Robertovich Malyshev and Angelina Nikolaevna Kravchenko},
title = {Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.030},
number = {3},
pages = {317--319},
doi = {10.1016/j.mencom.2018.05.030}
}
MLA
Cite this
MLA Copy
Anikina, Lada Vladimirovna, et al. “Preparative synthesis and pharmacological activity of Albicar racemate and enantiomers.” Mendeleev Communications, vol. 28, no. 3, Apr. 2018, pp. 317-319. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.030.

Abstract

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.

References

1.
Synthesis of glycolurils and their analogues
Kravchenko A.N., Baranov V.V., Gazieva G.A.
Russian Chemical Reviews, 2018
2.
Thermodynamics of Lithium Intercalation into Fluorinated Carbon Materials
Yazami R., Kusuzaka K., Hamwi A.
ECS Meeting Abstracts, 2008
3.
10.1016/j.mencom.2018.05.030_sbref0005c
Mashkovskii
2016
4.
Chemico-Pharmaceutical Analysis of the Biologically Active Substances Albicar
Berlyand A.S., Lebedev O.V., Prokopov A.A.
Pharmaceutical Chemistry Journal, 2013
5.
Experimental Pharmacokinetics of Bicaret
Prokopov A.A., Berlyand A.S., Kazantseva O.N.
Pharmaceutical Chemistry Journal, 2003
6.
Studies of the Hydrolytic Stability of the Biologically Active Substance Bicaret
Berlyand A.S., Prokopov A.A.
Pharmaceutical Chemistry Journal, 2014
7.
Neuroprotective activity of (+)-(S)-2-[(1S,5R)-(3,7-dioxo-2,4,6,8- tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid
Kravchenko A.N., Baranov V.V., Anikina L.V., Vikharev Y.B., Bushmarinov I.S., Nelyubina Y.V.
Russian Journal of Bioorganic Chemistry, 2012
8.
Ryzhkina I.S., Kiseleva Y.V., Mishina O.A., Timosheva A.P., Sergeeva S.Y., Kravchenko A.N., Konovalov A.I.
Mendeleev Communications, 2013
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.
Russian Journal of Inorganic Chemistry, 2007
10.
Features of self-organization of highly dilute solutions of (S)-, (R)-, and (SR)-methionines and related carbamides and glycolurils
Ryzhkina I.S., Sergeeva S.Y., Masagutova E.M., Murtazina L.I., Mishina O.A., Timosheva A.P., Baranov V.V., Kravchenko A.N., Konovalov A.I.
Russian Chemical Bulletin, 2015
12.
Kostyanovsky R.G., Kadorkina G.K., Lyssenko K.A., Torbeev V.Y., Kravchenko A.N., Lebedev O.V., Grintselev-Knyazev G.V., Kostyanovsky V.R.
Mendeleev Communications, 2002
13.
10.1016/j.mencom.2018.05.030_sbref0010b
Pletnev
Russ. J. Bioorg. Chem., 1993
14.
Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide
Chen J., Natte K., Spannenberg A., Neumann H., Beller M., Wu X.
Organic and Biomolecular Chemistry, 2014
15.
10.1016/j.mencom.2018.05.030_sbref0015b
Satyanarayana
Int. J. Chem. Tech. Res., 2011
16.
The CYP2B6*6 Allele Significantly Alters the N-Demethylation of Ketamine Enantiomers In Vitro
Li Y., Coller J.K., Hutchinson M.R., Klein K., Zanger U.M., Stanley N.J., Abell A.D., Somogyi A.A.
Drug Metabolism and Disposition, 2013
17.
A Concise Two-Step Synthesis of Thalidomide
Muller G.W., Konnecke W.E., Smith A.M., Khetani V.D.
Organic Process Research and Development, 1999
19.
A convenient asymmetric synthesis of thalidomide
Robin S., Zhu J., Galons H., Chuong P., Claude J.R., Tomas A., Viossat B.
Tetrahedron Asymmetry, 1995
20.
10.1016/j.mencom.2018.05.030_sbref0015g
Park
J. Int. Eng. Chem., 2002
21.
Three-dimensional structures and spectra of 2,6- and 2,8-diethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-diones
Shamuratov �.B., Batsanov A.S., Struchkov Y.T., Tsivadze A.Y., Tsintsadze M.G., Khmel'nitskii L.I., Simonov Y.A., Dvorkin A.A., Lebedev O.V., Markova T.B.
Chemistry of Heterocyclic Compounds, 1991
23.
Revisiting the open-field test: what does it really tell us about animal personality?
Perals D., Griffin A.S., Bartomeus I., Sol D.
Animal Behaviour, 2017
24.
Behavioral effects of antiepileptic drugs in rats: Are the effects on mood and behavior detectable in open-field test?
Zimcikova E., Simko J., Karesova I., Kremlacek J., Malakova J.
Seizure : the journal of the British Epilepsy Association, 2017
25.
10.1016/j.mencom.2018.05.030_sbref0025c
Chaves
Metab. Brain Dis., 2017
26.
10.1016/j.mencom.2018.05.030_sbref0025d
Bossier
Thérapie, 1964
27.
The Flavonoid Glycosides, Myricitrin, Gossypin and Naringin Exert Anxiolytic Action in Mice
Fernandez S.P., Nguyen M., Yow T.T., Chu C., Johnston G.A., Hanrahan J.R., Chebib M.
Neurochemical Research, 2009
28.
A. V. Val’dman and V. P. Poschivalov, Farmakologicheskaya regulyatsiya vnutrividovogo povedeniya (Pharmacological Regulation of Intraspecific Behaviour), Meditsina, Leningrad, 1984 (in Russian).
29.
https://amt.allergist.ru/mebicar_l.html.