ISSN 1070-4272, Russian Journal of Applied Chemistry, 2007, Vol. 80, No. 3, pp. 506 !508. + Pleiades Publishing, Ltd., 2007.
Original Russian Text + D.V. Bessonov, I.V. Kulakov, A.M. Gazaliev, O.A. Nurkenov, 2007, published in Zhurnal Prikladnoi Khimii, 2007, Vol. 80,
No. 3, pp. 510 !512.
Synthesis of Glycoconjugates of Physiologically
D. V. Bessonov, I. V. Kulakov, A. M. Gazaliev, and O. A. Nurkenov
Institute of Organic Synthesis and Coal Fuel Chemistry of Kazakhstan Republic, Limited Liability Company,
Received August 3, 2006
Abstract-Synthesis of N-glycosylamines derived from D-glucose and D-galactose (glycoconjugates of
aniline derivatives and of d-pseudoephedrine and cytisine alkaloids) was studied with the aim to develop new
N-Glycosylamines find growing use for preparing
natural glycopeptides, their analogs, and glycocon-
jugates used for various biological studies. N-Glyco-
sylamines, the reaction products of carbohydrates with
alkyl- and arylamines, attract attention of chemists,
biochemists, and biologists. N-Glycosylamines can
also be used for preparing new pharmaceuticals .
It is known than aniline is an antipyretic. However,
it is too toxic to be used as a pharmaceutical. Intro-
duction of various substituents into the benzene ring
or the amino groups yields compounds with a wide
range of pharmacological properties. Halogenation in-
creases the lipophilicity of pharmaceuticals and facili-
tates their penetration through biomembranes . For
example, p-thiocyanatoaniline is a strong insecticide
, and p-bromoaniline is a precursor for preparing
Fenazepam, which is a tranquilizer with hypnotic and
anticonvulsant effect .
N-Glycosylamines were prepared by condensation
of p-substituted anilines and D-glucose (1, 3, 5)or
D-galactose (2, 4, 6). Their biological activity was
studied. The condensation was performed in an al-
coholic solution on heating by the procedure described
1, 3, 5
2, 4, 6
1, 2 3, 4
N-Glycosylamines 1!6 are white crystalline com-
pounds readily soluble in water, ethanol, and DMF.
The presence of the band at 891+ 7cm
IR spectra of compounds 1!6 suggests the b-confor-