ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 7, pp. 1459–1460. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © O.A. Nurkenov, Zh.S. Akhmetkarimova, Zh.Kh. Muldakhmetov, A.E. Arinova, R.A. Ermukhanbetova, 2013, published in Zhurnal
Obshchei Khimii, 2013, Vol. 83, No. 7, pp. 1213–1214.
LETTERS
TO THE EDITOR
Synthesis and Structure of N-Aminoglycosides Based
on p-Aminoacetophenone
O. A. Nurkenova, Zh. S. Akhmetkarimovaa, Zh. Kh. Muldakhmetova,
A. E. Arinovaa, and R. A. Ermukhanbetovab
a Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan,
ul. Alikhanova 1, Karaganda, 100008 Kazakhstan
e-mail: nurkenov_oral@mail.ru
b Kazahstan Peoples’ Friendship University, Сhymkent, Kazakhstan
Received March 21, 2013
DOI: 10.1134/S1070363213070281
Nowadays antibiotics, antiviral and anticancer
drugs based on amino glycoside derivatives are widely
used in medicine [1]. N-Glycosylation of many amino
compounds is considered as a new approach to the
synthesis of promising and effective pharma-ceuticals
of directed action due to active transport of
carbohydrate fragments [2, 3].
new N-amino-glycosides ІII, IV, which can be further
modified, were synthesized for the first time via
condensation of monosaccharide (D-glucose and D-
galactose) with p-aminoacetophenone in a yield of 55–
70%. The synthesis of N-aminoglycosides ІII, IV was
carried out by the well-known classical method via the
direct condensation of the starting amine with
monosaccharides in an alcohol solution in the presence
of 2–3 drops of acetic acid as a catalyst.
Aiming to search potential biologically active
substances and to obtain substrates for the synthesis of
O
O
ethanol
−H2O
NH
NH2
CH3
Sug(OH) +
Sugb1
C
C
CH3
2
I, II
III, IV
Sug = D-Glc (III), D-Gal (IV).
The structure of the synthesized aminoglycoside
(1Н, Н1, JHH 8.1), 6.74 d (1Н, Нβ1, JHH 8.7), 7.73 d (1Н,
Нα1, JHH 8.7), 4.37 d (1H, OH4, J 4.1), 4.74 d (1Н, OH2,
J 5.6), 4.72 d (1H, OH3, J 5.4), 4.52 t (1H, OH6, J 5.4),
7.06 d (1H, NH, J 7.7). Found, %: C 59.93; H 9.85; N
3.78. C18H35NO6. Calculated, %: C 59.81; H 9.76; N
3.87.
1
derivatives ІII, IV was confirmed by the IR and H
NMR spectroscopy methods.
N-(4-Acetylphenyl)-β-D-glucopyranosylamine
(ІII). A mixture of 1.21 g (0.01 mol) of p-amino-
acetophenone and 1.8 g (0.01 mol) of D-glucose I in
20 ml of anhydrous ethanol with few drops of glacial
acetic acid was stirred at 55–60°C for 8 h. The reaction
mixture was kept for one day in the cold (from –15 to
–20°C). The formed gelatinous residue was washed
several times with hexane and recrystallized from
ethanol. Yield 1.52 g (55%), beige powder, mp 225°C.
IR spectrum, ν, cm–1: 3405 (ОН), 1010 (carbohydrate).
1Н NMR spectrum, δ, ppm (J, Hz): 2.42 s [3Н,
СН3C(O)], 3.38–3.54 m (6Н, carbohydrate), 4.42 t
N-(4-Acetylphenyl)-β-D-galactopyranosylamine
(IV) was prepared similarly from 1.21 g (0.01 mol) of
p-aminoacetophenone and 1.8 g (0.01 mol) of D-
galactose II. Yield 2.51 g (70%), mp 165°C. IR
spectrum, ν, cm–1: 3495 s (ОН), 1050 s (carbohydrate).
1Н NMR spectrum, δ, ppm (J, Hz): 2.42 s [3Н,
СН3C(O)], 3.43–3.57 m (6Н, carbohydrate), 4.43 t
(1Н, Н1, JHH 7.9), 6.73 d (1Н, Нβ1, JHH 8.8); 7.74 d (1Н,
Нα1, JHH 8.7), 4.53 d (1H, OH4, J 3.7), 4.8 d (1Н, OH2,
1459
Nurkenov
