Isoniazid Conjugates with D-Arabinofuranose

Article abstract of DOI:10.1134/S1070363218070101

Glycoconjugates with isoniazid attached to the hydroxy group at the С⁵ atom of D-arabinofuranose via the spacers differing in length have been synthesized.

Full text of DOI:10.1134/S1070363218070101

ISSN 1070-3632, Russian Journal of General Chemistry, 2018, Vol. 88, No. 7, pp. 1411–1417. © Pleiades Publishing, Ltd., 2018.
Original Russian Text © O.V. Andreeva, V.E. Kataev, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 7, pp. 1119–1125.
Isoniazid Conjugates with D-Arabinofuranose
O. V. Andreevaa and V. E. Kataeva*
a Arbuzov Institute of Organic and Physical Chemistry, Kazan Science Center, Russian Academy of Sciences,
ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420088 Russia
*e-mail: kataev@iopc.ru
Received March 22, 2018
Abstract―Glycoconjugates with isoniazid attached to the hydroxy group at the С5 atom of D-arabinofuranose
via the spacers differing in length have been synthesized.
Keywords: isoniazid, arabinofuranose, glycoconjugates
DOI: 10.1134/S1070363218070101
β-D-Arabinofuranosyl-1-О-monophosphodecaprenol
1 has been recognized as an exclusive source of D-
arabinose involved in the synthesis of arabinogalactan
and lipoarabinomannan, major components of cell
wall of mycobacteria [1, 2]. Since the biosynthesis of
these glycans is decisive in the survival of
mycobacteria, it has been suggested that the inhibitors
of this process should be efficient antibacterial and
antimycobacterial agents [3]. Such inhibitors are
searched among mimetics of decaprenylphosphoryl-
arabinose 1, glycolipids of general formula 2 with
arabinofuranose [2, 4], glucopyranose [5], glucosamine
[6–8], galactopyranose [9, 10], mannopyranose [11,
12], or glucuronic acid [13] as the carbohydrate block.
Phosphate [5, 11–13] and diphosphate [6–9] groups
have been used as the phosphorus-containing fragment.
The lipid moiety included prenyl, farnesyl, decyl, or
cetyl fragment as well as other polymethylene chains.
Since the hydroxy group at the С5 atom of the
arabinofuranose moiety of decaprenylphosphorylara-
binose 1 is involved in the growth of the oligo-
saccharide chain of arabinogalactans, it has been
Scheme 1.
O
P
OH
O
O
O
8
OH
HO
OH
1
OH
lipid
O
phosphorus
saccharide
2
H
n
O
P
N
O
NH
m
O
O
CH3
O
OH
N
HO
OH
3
1411

1412
ANDREEVA, KATAEV
Scheme 2.
Ph
Ph
Ph
Ph
Ph
Ph
O
OH
O
OH
OH
O
O
O
O
OAc
a
OH
OAc
c
b
HO
AcO
AcO
HO
OAc
OH
OH
OAc
5
7
4
6
O
H
H
N
O
N
O
O
N
H
O
NH2
O
O
OH
7
d
N
N
8
9
O
HO
O
O
O
O
OH
O
O
O
e, f
OAc
OAc
d
AcO
AcO
OAc
OAc
7
11
O
H
N
O
O
N
H
O
O
OAc
N
AcO
OAc
10
a, TrCl, Py, 25°C; b, Ac2O, Py, 0°C; c, AcOH, H2O, 80°C; d, СН2Сl2, Py, DMAP, 25°C; e, CO2Cl2, CH2Cl2, 25°C; f,
isoniazid 8, Py, CH2Cl2, 25°C.
substituted with a halogen atom, methoxy, amino,
azido, acetamido, or other groups in certain mimetics
to inhibit the said process [4, 14].
the target glycolipids 3, conjugates of isoniazid and D-
arabinofuranose 10, 17, and 21.
By analogy with [4], the first stage of the
conjugates synthesis involved the conversion of
commercial D-arabinose 4 into D-arabinofuranose 5
with simultaneous selective trityl protection of the С5
hydroxyl. The other hydroxy groups were then
converted into acetyl ones, and the trityl protection of
the arabinofuranoside 6 was removed with 80%
solution of acetic acid, with the formation of 1,2,3-tri-
In continuation of the search of antituberculous
agents among phosphorylated glycolipids [13], we
started the synthesis of mimetics of decaprenylphos-
phorylarabinose 1 of general formula 3, with isoniazid
molecule attached to the hydroxyl at the С5 atom of
arabinofuranose via the spacers differing in length.
Here we report on the synthesis of semi-products of
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ISONIAZID CONJUGATES WITH D-ARABINOFURANOSE
Scheme 3.
Ph
Ph
Ph
OH
O
OH
OH
O
O
O
OCH3
OCH3
а
b
HO
HO
HO
HO
OH
OH
4
OH
12
13
Ph
O
Ph
Ph
O
O
O
O
OH
O
O
O
O
O
OCH3
OCH3
d
OCH3
c
e
BnO
BnO
BnO
16
OBn
OBn
OBn
14
15
O
H
O
N
O
N
H
O
O
f
OCH3
N
BnO
OBn
17
O
O
O
O
g
(CH2)8
18
(CH2)8
OH
Cl
HO
OH
Cl
19
O
O
OH
O
O
OCH3
O
OCH3
h
O
BnO
BnO
OBn
OBn
15
20
HN
NH
N
O
O
f
O
O
OCH3
BnO
OBn
21
a, CH3OH, HCl, 25°C; b, TrCl, Py, 25°C; c, DMF, NaH, C6H5CH2Br, 0°C; d, AcOH, H2O, 80°C; e, СН2Сl2, Py, DMAP, 25°
C; f, DCC, DMAP, Py, isoniazid 8, 25°C; g, SOCl2, CH2Cl2, 25°C; h, CH2Cl2, Et3N, 25°C.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 88 No. 7 2018

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ANDREEVA, KATAEV
О-acetyl-5-hydroxy-D-arabinofuranose 7 (Scheme 2).
The second stage involved the reaction of isoniazid 8
with succinic anhydride. Dioxane, ethyl acetate, or
mixture of ethyl acetate with water are usually used as
solvents for the reactions of hydrazides with cyclic
anhydrides [15, 16]. However, following [17], we
performed the reaction in ethanol under reflux, which
allowed isolation of pure product 9 from the reaction
mixture without additional purification. Unfortunately,
acid 9 was insoluble in organic solvents, and it was
impossible to perform its reaction with arabino-
furanoside 7 to prepare conjugate 10.
having afforded methyl 2,3-di-О-benzyl-5-succinyl-β-
D-arabinofuranoside 16 in 86% yield. Its formation
was evidenced by the presence of the signals at m/z
467.2 [M + Na]+ (C24H28NaO8, M 467.17) and m/z
483.2 [M + K]+ (C24H28KO8, M 483.14) in the mass
spectrum. The interaction of arabinofuranoside 16 with
isoniazid
8
performed similarly to [21] gave
(according to the mass spectral data) conjugate 17
(Scheme 3) isolated by chromatography in 27% yield.
Its formation was confirmed by the presence of a
single signal at m/z 586.3 [M + Na]+ (C30H33N3NaO8,
M 586.22) in the mass spectrum. 1Н NMR spectrum of
conjugate 17 contained the multiplets at 7.7 and 8.6
ppm corresponding to the resonance of the protons of
the pyridine ring of the isonicotinoyl fragment, on top
of the signals assigned to the protons of the arabino-
furanose and the succinic acid moieties.
In view of that, we performed the interaction of
arabinofuranoside 7 with succinic anhydride, leading
to 1,2,3-tri-О-acetyl-5-succinyl-D-arabinofuranoside 11
in 66% yield (Scheme 2). Its formation was confirmed
by the presence of a single peak in the ESI mass
spectrum, at m/z 399.2 [M + Na]+ (C15H20NaO11,
M 399.09). The presence of two types of signals in the
1Н NMR spectrum of arabinofuranoside 11 assigned to
the resonance of anomeric proton evidenced the formation
of approximately equal amounts of α- and β-anomer
forms. According to the reference data of [18–20] the
singlet at 6.09 ppm was assigned to the α-anomer, and
the doublet at 6.28 ppm with the vicinal spin-spin
interaction constant 4.4 Hz was assigned to the β-anomer.
To prepare the conjugate of isoniazid with D-ara-
binofuranose containing a longer spacer, methyl 2,3-di-
О-benzyl-α-D-arabinofuranoside 15 was involved in
the reaction with sebacyl chloride 19 (Scheme 3)
prepared via the interaction of sebacic acid 18 with
thionyl chloride. The reaction led to the formation of
methyl 2,3-di-О-benzyl-5-sebacyl-α-D-arabinofuranoside
20 isolated by chromatography with 33% yield. Its
formation was confirmed by the presence of the signals
at m/z 551.17 [M + Na]+ (C30H40NaO8, M 551.26) and
m/z 567.18 [M + K]+ (C30H40KO8, M 567.24) in the
mass spectrum. In the 1H NMR spectrum, the anomeric
proton appeared as a singlet at 4.94 ppm evidencing
the existence of arabinofuranoside 20 as the α-anomer.
The interaction of arabinofuranoside 11 with
isoniazid 8 performed as described in [21] gave
conjugate 10 (Scheme 2) according to the mass
spectrometry data. The MALDI mass spectrum of the
reaction mixture contained the peaks at m/z 518.1 [M +
Na]+ (C21H25N3NaO11, M 518.14) and m/z 534.1 [M +
K]+ (C21H25KN3O11, M 534.11). Unfortunately, we
failed to isolate pure conjugate 10. To avoid the
formation of the open-chain form, methoxy group was
attached at the C1 anomeric atom of arabinofuranose
via the interaction of D-arabinose 4 with methanol [22].
Finally, the acid 20 was involved in the reaction
with isoniazid 8 under conditions similar to the syn-
thesis of conjugate 17. The chromatography on silica
gel afforded conjugate 21 in 25% yield. Its formation
was confirmed by the presence of a single signal at m/z
670.2 [M + Na]+ (C36H45N3NaO8, М 670.31) in the
1
mass spectrum. The Н NMR spectrum of conjugate
Further selective protection-deprotection (as in
[23]) afforded methyl 2,3-di-О-benzyl-D-arabinofura-
noside 15 (Scheme 3), and its α- and β-anomers were
21 contained the doublets at 7.62 ppm (vicinal spin-
spin coupling constant 5.5 Hz) and 8.68 ppm (vicinal
spin-spin coupling constant 4.9 Hz) corresponding to
the resonance of the protons of the pyridine ring of the
isonicotinoyl fragment, on top of the signals assigned
to the protons of the arabinofuranose and sebacic acid
moieties. The anomeric proton of conjugate 21 ap-
1
isolated by chromatography on silica gel. Н NMR
spectra of isomers of arabinofuranoside 15 showed the
resonance of the anomeric proton of the β-anomer at
4.60 ppm as a doublet with a vicinal coupling constant
of 4.5 Hz, and the anomeric proton of the α-isomer
appeared as a singlet at 4.96 coinciding with the
reference data ([18] and [19, 20], respectively).
1
peared as a singlet at 4.92 ppm in the Н NMR
spectrum confirming the preservation of the α-orienta-
tion of the glycoside bond.
The β-anomer of arabinofuranoside 15 was then
involved in the reaction with succinic anhydride,
In summary, we performed the first step of the syn-
thesis of target mimetics of decaprenylphosphoryl-
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ISONIAZID CONJUGATES WITH D-ARABINOFURANOSE
arabinose 1 of general formula 3. The first conjugates
of isoniazid with D-arabinofuranose 17 and 21 were
prepared. The second step which will be described in
the upcoming report will include the substitution of the
anomeric methoxy group of the conjugates 17 and 21
with bromine atoms, phosphorylation of the obtained
conjugates with esters of phosphoric acid containing
lipid groups, and removal of the benzyl protection.
arabinofuranoside 7 in 5 mL of methylene chloride.
The reaction mixture was stirred at room temperature
during 18 h, 3 mL of water was then added, and the
stirring was continued for 3 h. The mixture was con-
centrated at a reduced pressure, dissolved in 100 mL of
methylene chloride, washed with water, and dried over
MgSO4. Methylene chloride was removed at a reduced
pressure, and the residue was recrystallized from a 1 : 1
mixture of petroleum ether and ethyl acetate. DMAP
crystals were filtered off, the solvent was removed
from the filtrate, and the residue was dried at a reduced
pressure. Yield 0.67 g (66%), colorless substance,
EXPERIMENTAL
1Н and 13C NMR spectra were recorded using
Avance-400 and Avance-600 spectrometers (Bruker,
Germany). MALDI mass spectra were registered in the
linear mode using a UltraFlex III TOF/TOF mass
spectrometer (Bruker Daltonik GmbH, Germany)
equipped with a Nd:YAG laser, λ 355 nm. The data
were processed using FlexAnalysis 3.0 software
(Bruker Daltonik GmbH, Germany). The measurements
were performed over the m/z 200–6000 Da range in the
positive ions mode using a metallic target, with 2,5-
dihydroxybenzoic acid and para-nitroaniline as the
matrix. Electrospray ionization (ESI) mass spectra
were registered using an AmazonX mass spectrometer
(Bruker Daltonik GmbH, Germany). The measurements
were performed over the m/z 100–1500 Da range in the
negative ions mode, the capillary voltage being 4500 V.
Optical rotation was measured using a Perkin Elmer-
341 polarimeter (USA). The reactions completeness
and the products purity were monitored by thin layer
chromatography on Sorbfil plates (Imid, Russia); the
substances were visualized by treatment with 5%
solution of sulfiric acid followed by heating to 120°C
or by UV irradiation.
[α]D20 6.5° (с 1.1, CH3OH). Н NMR spectrum (400
1
MHz, СDСl3), δ, ppm: 1.98–2.04 m (18Н, CH3CO),
2.58 q (8Н, CH2, J = 3.0 Hz), 4.10–4.36 m (8Н, H4,5),
4.98 d.d (1Н, H3α, J = 4.5, 0.9 Hz), 5.12 d (1Н, H2α, J =
1.3 Hz), 5.22–5.30 m (2Н, Н2β,3β), 6.09 s (1Н, Н1α),
6.28 d (1Н, Н1β, J = 4.4 Hz), 13.1 br.s (2Н, ОН). 13C
NMR spectrum (100 MHz, СD3Cl), δC, ppm: 20.23,
20.48, 20.49, 20.52, 20.82, 20.85 (OCOCH3), 28.89,
28.92 (CH2CH2), 53.34 (OCH3), 62.99, 64.56 (C2),
74.67, 75.21 (C5), 76.72, 79.44 (C3), 80.45, 82.15 (C4),
93.56, 99.18 (C1), 169.13, 169.37, 169.61, 169.82,
170.09, 171.88 (C=O). Mass spectrum (ESI), m/z (Irel,
%): 399.2 (100) [M + Na]+. Found, %: С 47.96; Н
5.93. C15H20O11. Calculated, %: С 47.88; Н 5.36.
Methyl 2,3-di-O-benzyl-5-succinyl-β-D-arabino-
furanoside (16). A solution of 0.4 g (4 mmol) of
succinic anhydride and 0.1 g (0.8 mmol) of DMAP in
10 mL of pyridine was added to a solution of 0.3 g
(0.9 mmol) of compound 15 in 5 mL of methylene
chloride. The reaction mixture was stirred at room tem-
perature during 18 h, 3 mL of water was then added,
and the stirring was continued for 3 h. The mixture
was concentrated at a reduced pressure, dissolved in
100 mL of methylene chloride, washed with water, and
dried over MgSO4. Methylene chloride was removed at
a reduced pressure, and the residue was recrystallized
from a 1 : 1 mixture of petroleum ether and ethyl
acetate. DMAP crystals were filtered off, the solvent
was removed from the filtrate, and the residue was
dried at a reduced pressure. Yield 0.3 g (86%), pale
yellow substance. 1Н NMR spectrum (400 MHz,
СDСl3), δ, ppm: 2.61 br.s (4Н, CH2СН2), 3.33 s (3Н,
OCH3), 4.02–4.21 m (5Н, H2–5), 4.58–4.72 m (5Н,
СH2C6H5, H1), 7.23–7.38 m (10Н, C6H5), 11.3 br.s
(1Н, ОН). 13C NMR spectrum (100 MHz, СD3Cl), δC,
ppm: 28.79, 28.90 (CH2CH2), 54.87 (OCH3), 63.85
(C2), 72.00, 72.21 (CH2C6H5), 79.22 (C5), 83.28 (C3),
87.84 (C4), 107.24 (C1), 127.89, 127.91, 127.94,
Compounds 5, 6, and 7 were prepared as described
elsewhere [4]. Compound 9 was prepared by a method
described in [17]; its melting point and spectral
properties coincided with the reference data [15, 16].
Arabinofuranoside 12 was prepared as described in
[22], and arabinofuranosides 13 and 14 were syn-
thesized following [23]; their spectral parameters
coincided with the reference data. Arabinofuranoside
15 was obtained as described in [23]; its protons
signals coincided with the reference data [18–20].
Commercial D-arabinose 4 (Acros, Belgium) and
isoniazid 8 (Merck, Germany) were used.
1,2,3-Tri-O-acetyl-5-succinyl-α/β-D-arabinofuranose
(11). A solution of 0.6 g (6 mmol) of succinic an-
hydride and 0.6 g (5.3 mmol) of DMAP in 10 mL of
pyridine was added to a solution of 0.4 g (1.4 mmol) of
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ANDREEVA, KATAEV
127.97, 128.45, 128.49, 137.38, 137.56 (2C6H5),
171.93, 177.00 (C=O). Mass spectrum (MALDI), m/z
(Irel, %): 467.21 (50) [M + Na]+, 483.15 (100) [M + K]+.
Found, %: С 64.91; Н 6.43. C24H28O8. Calculated, %:
С 64.85; Н 6.35.
(C3), 88.02 (C4), 101.70 (C1), 127.22, 127.81, 127.83,
127.89, 128.15, 128.39, 128.41 (2C6H5), 173.48,
174.21 (C=O). Mass spectrum (MALDI), m/z (Irel, %):
551.17 (100) [M + Na]+, 567.18 (30) [M + K]+. Found,
%: С 68.31; Н 7.49. C30H40O8. Calculated, %: С 68.16;
Н 7.63.
Methyl 2,3-di-О-benzyl-5-(isonicotinoylhydrazino-
carbonylethylenecarboxyl)-β-D-arabinofuranoside
(17). 0.65 g (3.1 mmol) of N,N'-dicyclohexylcarbo-
diimide and 0.05 g (0.4 mmol) of DMAP was added to
a solution of 0.35 g (0.79 mmol) of acid 16 and 0.45 g
(3.2 mmol) of isoniazid 8 in 30 mL of pyridine. The
solution was stirred during 24 h on a bath at 30°С.
Pyridine was then removed at a reduced pressure, and
the residue was purified by chromatography on silica
gel (eluent: petroleum ether––ethyl acetate, 5 : 1 to 1 : 3
and ethyl acetate). Yield 0.12 g (27%), yellow
Methyl 2,3-di-О-benzyl-5-(isonicotinoylhydrazino-
carbonyloctamethylenecarcoxyl)-α-D-arabinofura-
noside (21). 0.1 g (0.48 mmol) of N,N'-dicyclohexyl-
carbodiimide and 0.06 g (0.54 mmol) of DMAP were
added to a solution of 0.13 g (0.25 mmol) of arabino-
furanoside 20 and 0.07 g (0.51 mmol) of isoniazid 8 in
50 mL of pyridine. The solution was stirred during 24 h
on a bath at 30°С. Pyridine was removed at a reduced
pressure, and the residue was purified by chromato-
graphy on silica gel (eluent: petroleum ether––ethyl
acetate, 10 : 1 to 1 : 2, ethyl acetate). Yield 0.04 g
1
substance. Н NMR spectrum (400 MHz, СD3OD), δ,
1
ppm: 2.60–2.72 m (4Н, CH2CH2), 3.33 s (3Н, OCH3),
4.03–4.21 m (5Н, H2–5), 4.53–4.69 m (5Н, СH2C6H5,
H1), 7.22–7.38 m (10Н, C6H5), 7.75–7.79 m (2Н,
C5H4N), 8.65–8.69 m (2Н, C5H4N). 13C NMR
spectrum (100 MHz, СD3OD), δC, ppm: 29.39, 30.03
(CH2CH2), 55.46 (OCH3), 66.82 (C2), 73.46, 73.61
(CH2C6H5), 80.23 (C5), 83.27 (C3), 85.55 (C4), 103.06
(C1), 123.12 (C5H4N), 128.84, 129.05, 129.43, 129.47
(2C6H5), 139.13, 139.49, 151.01 (C5H4N), 166.77
[С(O)NH], 173.41, 173.75 (C=O). Mass spectrum
(MALDI), m/z (Irel, %): 586.28 (100) [M + Na]+.
Found, %: С 63.78; Н 5.98; N 7.39. C30H33N3O8.
Calculated, %: С 63.93; Н 5.90; N 7.46.
(25%), yellow substance. Н NMR spectrum (600
MHz, СDСl3), δ, ppm: 1.27 br.s (8Н, CH2), 1.54–1.69
m (4Н, CH2), 2.25–2.33 m (4Н CH2C=O), 3.37 s (3Н,
ОСH3), 3.82 d.d (1Н, H2, J = 2.7, 6.6 Hz), 3.99 d (1Н,
H4, J = 2.2 Hz), 4.13–4.22 m (3Н, H5), 4.27 d.d (1Н,
H3, J = 2.7, 11.5 Hz), 4.45–4.59 m (4Н, СH2C6H5),
4.92 s (1Н, H1), 7.24–7.38 m (10Н, C6H5), 7.62 d (2Н,
C5H4N, J = 5.5 Hz), 8.68 d (2Н, C5H4N, J = 4.9 Hz),
8.95 br.s (1Н, NH), 10.03 br.s (NH). 13C NMR
spectrum (100 MHz, СDСl3), δC, ppm: 24.67, 28.93,
33.96 (CH2), 54.91 (OCH3), 63.64 (C2), 72.04, 72.24
(CH2C6H5), 79.32 (C5), 83.44 (C3), 87.88 (C4), 107.29
(C1), 120.96 (C5H4N), 127.81, 127.83, 127.9, 128.39,
128.41 (2C6H5), 137.55, 150.46, 150.51 (C5H4N),
162.83 [С(O)NH], 171.51, 173.52 (C=O). Mass
spectrum (MALDI), m/z (Irel, %): 670.19 (100) [M +
Na]. Found, %: С 66.67; Н 7.12, N 6.43. C36H45N3O8.
Calculated, %: С 66.75; Н 7.00, N 6.49.
Methyl 2,3-di-O-benzyl-5-sebacyl-α-D-arabino-
furanoside (20). A solution of arabinofuranoside 15 in
20 mL of methylene chloride and three drops of
triethylamine were slowly added to a solution of 0.3 g
sebacyl dichloride 19 in 60 mL of anhydrous me-
thylene chloride. The mixture was stirred at room tem-
perature. When arabinofuranoside 15 was completely
consumed, methylene chloride was removed at a
reduced pressure, and the residue was purified by
chromatography on silica gel (eluent: petroleum ether–
ethyl acetate, 10 : 1 to 6 : 1). Yield 0.13 g (33%), pale
yellow substance. 1Н NMR spectrum (400 MHz,
СDСl3), δ, ppm: 1.29 br.s (8Н, CH2), 1.54–1.67 m
(4Н, CH2), 2.26–2.36 m (4Н CH2C=O), 3.39 s (3Н,
ОСH3), 3.85 d.d (1Н, H2, J = 2.8, 5.1 Hz), 4.01 d.d
(1Н, H4, J = 1.1, 2.9 Hz), 4.15–4.32 m (3Н, H3,5), 4.46–
4.51 m (4Н, СH2C6H5), 4.94 s (1Н, H1), 7.26–7.39 m
(10Н, C6H5). 13C NMR spectrum (100 MHz, СDCl3),
δC, ppm: 24.86, 28.99, 34.02 (CH2), 54.93 (OCH3),
63.54 (C2), 72.04, 72.25 (CH2C6H5), 79.33 (C5), 82.30
ACKNOWLEDGMENTS
This study was financially supported by the Russian
Science Foundation (grant no. 14-50-00014).
CONFLICT OF INTERESTS
No conflict of interest was declared by the authors.
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