Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents

Article abstract of DOI:10.1134/S1070428014120094

Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 μg/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.

Full text of DOI:10.1134/S1070428014120094

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 12, pp. 1767–1774. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © L.V. Chinh, T.N. Hung, N.T. Nga, T.T.N. Hang, T.T.N. Mai, V.A. Tarasevich, 2014, published in Zhurnal Organicheskoi Khimii, 2014,
Vol. 50, No. 12, pp. 1786–1793.
Synthesis and Antimicrobial Activity of Chalcones Containing
Benzotriazolylmethyl and Imidazolylmethyl Substituents
L. V. Chinha, T. N. Hunga, N. T. Ngaa, T. T. N. Hangb, T. T. N. Maia, and V. A. Tarasevichc
a Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, Hanoi, Vietnam
b Vietnam National University, Hanoi, Vietnam
c Institute of New Materials Chemistry, National Academy of Sciences of Belarus,
ul. F. Skoriny 36, Minsk, 220141 Belarus
e-mail: tar@ichnm.basnet.by
Received August 29, 2014
Abstract—Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imid-
azol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloro-
methylation, N-alkylation, and Claisen–Schmidt condensation. The presence of an imidazole fragment on the
ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity
(minimum inhibitory concentration 12.5–50.0 μg/mL), whereas introduction of a benzotriazole fragment
reduces the antimicrobial activity.
DOI: 10.1134/S1070428014120094
In recent years chalcone derivatives containing ni-
trogen heterocycles have attracted increased attention
due to broad spectrum of their biological activity [1],
in particular antifungal and antibacterial [2]. We
believed that introduction of triazole and imidazole
fragments into chalcone molecules could affect their
biological activity.
terconazole, and posaconazole [3–10], which are used
for the treatment of many systemic fungal infections.
New antifungal imidazole derivatives are now being
developed, and imidazole derivatives are widely
represented among numerous and efficient medicines.
Simultaneously, triazole derivatives are considered to
be promising drugs for antifungal chemotherapy due to
broad spectrum of their activity and reduced toxicity as
compared to imidazole analogs [11]. Nevertheless,
there are no published data on the synthesis and anti-
fungal or antibacterial activity of chalcones containing
benzotriazole and imidazole fragments attached to the
Imidazole and triazole derivatives constitute the
two main classes of antimicrobial azoles; imidazole
and triazole rings are structural fragments of well
known drugs, such as nitroimidazole, ketoconazole,
miconazole, albaconazole, fluconazole, isavuconazole,
Scheme 1.
O
O
O
i
ii or iii
Me
Cl
Me
R
Me
OH
OH
OH
I
II
III, IV
N
N
N
N
III, R =
; IV, R =
.
N
Reagents and conditions: i: paraformaldehyde, concd. aq. HCl, 35°C, 8 h; ii: benzotriazole, K2CO3, DMF, MW, 20 min;
iii: imidazole, K2CO3, DMF, MW, 20 min.
1767

CHINH et al.
1768
Scheme 2.
CHO
CHO
CHO
Cl
N
R
i
ii
MeO
MeO
MeO
Va
VI
VII–XI
Me
O
N
N
VII, R =
; VIII, R =
; IX–XI, R =
; IX, R′ = Me; X, R′ = Et; XI, R′ = Ph.
N
O
N
O
N
O
R'
H
H
Reagents and conditions: i: (1) 37% aq. formaldehyde, ZnCl2, concd. aq. HCl, 50°C, 30 min; (2) reflux; ii: 4-R-piperazine,
K2CO3, DMF, MW, 10 min.
benzaldehyde (Vc), 4-methylbenzaldehyde (Vd),
3-hydroxy-4-methoxybenzaldehyde (Ve, isovanillin),
3,4,5-trimethoxybenzaldehyde (Vf), 3-(2,4-dioxo-
1,2,3,4-tetrahydropyrimidin-1-ylmethyl)-4-methoxy-
benzaldehyde (VII), 4-methoxy-3-(5-methyl-2,4-di-
oxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl)benzal-
dehyde (VIII), 4-methoxy-3-(4-methylpiperazin-1-yl-
methyl)benzaldehyde (IX), 3-(4-ethylpiperazin-1-yl-
methyl)-4-methoxybenzaldehyde (X), and 4-methoxy-
3-(4-phenylpiperazin-1-ylmethyl)benzaldehyde (XI),
which afforded the corresponding benzotriazolyl-
methyl-substituted chalcones XIIa–XIIk in 46–67%
yield (Scheme 3) and imidazolylmethyl-substituted
analogs XIIIa–XIIIg in 45–70% yield (Scheme 4).
The reactions of ketone IV with aldehydes Vf and IX–
XI were accompanied by formation of many by-prod-
ucts, and we failed to isolate the desired chalcones.
ring A. To fill this gap, in the present work we syn-
thesized new chalcones with benzotriazolylmethyl and
imidazolylmethyl substituents and tested them for
antifungal and antibacterial activity.
The key intermediate products were prepared start-
ing from 2-hydroxyacetophenone (I). In the first step,
chloromethylation of 2-hydroxyacetophenone (I) ac-
cording to the known procedure [12] gave 5-chloro-
methyl-2-hydroxyacetophenone (II) which was used to
alkylate benzotriazole and imidazole under microwave
irradiation at 50°C (250 W, 20 min). We thus obtained
5-(1H-benzotriazol-1-ylmethyl)-2-hydroxyaceto-
phenone (III) and 2-hydroxy-5-(1H-imidazol-1-yl-
methyl)acetophenone (IV) in 55 and 59% yield, re-
spectively (Scheme 1).
By reaction of 4-methoxybenzaldehyde (Va) with
formaldehyde and HCl in the presence of ZnCl2 [13]
we synthesized 3-chloromethyl-4-methoxybenzalde-
hyde (VI) which was brought into reactions with
uracil, thymine, N-methylpiperazine, N-ethylpipera-
zine, and N-phenylpiperazine to obtain aldehydes VII–
XI (Scheme 2). Aldehydes VII and VIII were isolated
in 55–56% yield.
The product structure was confirmed by IR and
NMR spectroscopy and high-resolution mass spec-
1
trometry. Signals in the H and 13C NMR spectra of
compounds XIIk and XIIIa were assigned using
heteronuclear single quantum coherence (HSQC)
technique. It was found that signals from the ketone
moiety of all chalcones XII and XIII were generally
consistent with those of initial ketones III and IV and
that signals from the aldehyde moiety differed depend-
ing of the initial aldehyde.
The final step was the Claisen–Schmidt condensa-
tion of ketones III and IV with 4-methoxybenzalde-
hyde (Va), 3-methoxybenzaldehyde (Vb), 4-isopropyl-
Scheme 3.
6''
4''
7a''
O
O
R2
R1
CHO
5''
R2
R1
1''
N
1'
2'
5'
1
3
N
Me
+
4''
3a''
N
N
N
N
OH
OH
R3
Va–Vf, VII–XI
3''
5
R2
III
XIIa–XIIk
V, XII, R1 = OMe, R2 = R3 = H (a); R1 = R3 = H, R2 = OMe (b); R1 = i-Pr, R2 = R3 = H (c); R1 = Me, R2 = R3 = H (d); R1 = OMe,
R2 = OH, R3 = H (e); R1 = R2 = R3 = OMe (f); XII, R1 = OMe, R2 = 2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl, R3 = H (g);
R1 = R3 = H, R2 = 5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl (h); R1 = OMe, R2 = 4-methylpiperazin-1-ylmethyl,
R3 = H (i); R1 = OMe, R2 = 4-ethylpiperazin-1-ylmethyl, R3 = H (j); R1 = OMe, R2 = 4-phenylpiperazin-1-ylmethyl, R3 = H (k).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 12 2014

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF CHALCONES
1769
Scheme 4.
O
O
R2
R1
CHO
5''
R2
R1
1''
N
1'
2'
5'
1
3
N
Me
4''
+
2''
N
3'' N
OH
OH
R3
5
R2
IV
Va–Ve, VII, VIII
XIIIa–XIIIg
XIII, R1 = OMe, R2 = R3 = H (a), R1 = R3 = H, R2 = OMe (b), R1 = i-Pr, R2 = R3 = H (c), R1 = Me, R2 = R3 = H (d), R1 = OMe, R2 =
OH, R3 = H (e), R1 = OMe, R2 = 2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl, R3 = H (f), R1 = R3 = H, R2 = 5-methyl-2,4-di-
oxo-1,2,3,4-tetrahydropyrimidin-1-ylmethyl (g).
mp 128–130°C. IR spectrum, ν, cm–1: 3448 (O–H),
EXPERIMENTAL
3040 (C–H), 1640 (C=O), 1618 (C=C), 769 (δC–H).
1H NMR spectrum (DMSO-d6), δ, ppm: 2.63 s (3H,
The IR spectra were recorded in KBr on a Nicolet
Impact-410 spectrometer with Fourier transform. The
NMR spectra were measured on a Bruker Avance 500
instrument (500 MHz); the chemical shifts are given
relative to tetramethylsilane. The high-resolution mass
spectra were obtained on a Varian FT-ICR (Fourier
transform ion cyclotron resonance) mass spectrometer.
The progress of reactions was monitored by TLC on
Merck 60F254 silica gel plates; spots were visualized
using an UV lamp (λ 254 nm). Silica gel (40–
230 mesh) was used for column chromatography.
CH3), 5.93 s (2H, CH2), 6.93 d (1H, 3-H, J = 8.5 Hz),
7.39 t (1H, 5′-H, J = 7.5 Hz), 7.47 d.d (1H, 4-H, J =
2.0, 8.5 Hz), 7.53 t (1H, 6′-H, J = 7.5 Hz), 7.91 d (1H,
7-H, J = 8.5 Hz), 8.02 d (1H, 6-H, J = 2.0 Hz), 8.04 d
(1H, 4′-H, J = 8.5 Hz), 11.81 s (1H, OH). 13C NMR
spectrum (DMSO-d6), δC, ppm: 28.1, 50.3, 110.8,
118.2, 119.2, 120.7, 124.1, 126.7, 127.4, 131.0, 132.5,
135.6, 145.4, 160.2, 203.5. Found: m/z 268.10805
[M + H]+. C15H14N3O2. Calculated: M + H 268.10857.
1-[2-Hydroxy-5-(1H-imidazol-1-ylmethyl)-
phenyl]ethanone (IV). Yield 59%, light yellow crys-
tals, mp 96–98°C. IR spectrum, ν, cm–1: 3448 (O–H),
3141, 3094 (C–H), 1655 (C=O), 1511–1639 (C=C),
1-[5-(Chloromethyl)-2-hydroxyphenyl]ethanone
(II). Paraformaldehyde, 2.43 g (81 mmol), was added
to a solution of 9.9 g (73 mmol) of 2-hydroxyaceto-
phenone (I) in 160 mL of concentrated aqueous HCl.
The mixture was stirred for 8 h at 35°C, diluted with
water, and extracted with methylene chloride (3×
100 mL). The combined extracts were dried over anhy-
drous sodium sulfate, and the solvent was removed
under reduced pressure. Yield 10.0 g (75%), mp 77–
79°C. Compound II was used in further syntheses
without additional purification.
1
757 (δC–H). H NMR spectrum (DMSO-d6), δ, ppm:
2.62 s (3H, CH3), 5.13 s (2H, CH2), 6.90 s (1H, 4′-H),
6.95 d (1H, 3-H, J = 8.5 Hz), 7.21 s (1H, 5′-H),
7.44 d.d (1H, 4-H, J = 2.0, 8.5 Hz), 7.77 s (1H, 2′-H),
7.89 d (1H, 6-H, J = 2.0 Hz), 11.88 s (1H, OH).
13C NMR spectrum (DMSO-d6), δC, ppm: 27.9, 48.7,
118.0, 119.3, 120.5, 128.4, 128.7, 130.8, 135.7, 137.2,
160.2, 203.9. Found: m/z 217.09715 [M + H]+.
C12H13N2O2. Calculated: M + H 217.09772.
3-(Chloromethyl)-4-methoxybenzaldehyde (VI).
A mixture of 50 g (0.37 mol) of 4-methoxybenzalde-
hyde (Va), 75 g of 40% aqueous formaldehyde,
250 mL of 36% aqueous HCl, and 15 g (0.11 mol) of
zinc(II) chloride was vigorously stirred for 30 min at
50°C and was then heated for 30 min under reflux.
After cooling, the aqueous phase was removed, and the
organic phase was diluted with chloroform (200 mL),
washed with 10% aqueous sodium hydroxide and
water to neutral reaction, dried over anhydrous sodium
sulfate, and evaporated under reduced pressure. The
residue was recrystallized from hexane. Yield 57.6 g
(85%), mp 59–60.5°C.
Compounds III and IV (general procedure).
A mixture of 1.19 g (10 mmol) of benzotriazole or
0.68 g (10 mmol) of imidazole, 1.8 g (13.3 mmol) of
potassium carbonate, 2.07 g (15 mmol) of compound
II, and 238 mg of butyl(triethyl)ammonium bromide in
25 mL of anhydrous dimethylformamide was subjected
to microwave irradiation for 20 min under stirring at
50°C (250 W). The mixture was concentrated under
reduced pressure, and the residue was diluted with
chloroform (60 mL) and extracted with distilled water
(4×60 mL). The organic phase was separated, dried
over anhydrous sodium sulfate, and evaporated under
reduced pressure. The residue was recrystallized from
methanol (III) or ethyl acetate (IV).
1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hydroxy-
phenyl]ethanone (III). Yield 55%, white crystals,
Compounds VII and VIII (general procedure).
A mixture of 1.0 g (8.9 mmol) of uracil or 1.12 g
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 12 2014

CHINH et al.
1770
(8.9 mmol) of thymine, 1.8 g (13.3 mmol) of potas-
sium carbonate, 1.8 g (9.8 mmol) of 3-(chloromethyl)-
4-methoxybenzaldehyde (VI), and 212 mg of butyl-
(triethyl)ammonium bromide in 25 mL of anhydrous
dimethylformamide was vigorously stirred for 20 min
under microwave irradiation (70°C, 300 W). The
mixture was concentrated under reduced pressure, the
residue was diluted with chloroform (50 mL) and ex-
tracted with distilled water (3×50 mL), and the organic
phase was separated, dried over anhydrous sodium
sulfate, and concentrated under reduced pressure. The
residue was recrystallized from methanol.
sodium sulfate, and concentrated under reduced pres-
sure, and the residue was purified by column chroma-
tography using hexane–ethyl acetate as eluent.
Chalcones XIIa–XIIk and XIIIa–XIIIg (general
procedure). Potassium hydroxide, 224 mg (4 mmol),
was added to a mixture of 1 mmol of ketone III or IV
and 1.1 mmol of aldehyde Va–Vf or VII–XI in 15 mL
of anhydrous ethanol, and the mixture was stirred for
24 h at room temperature. The solvent was removed
under reduced pressure, and the residue was treated
with water, neutralized with 10% aqueous HCl, and
extracted with ethyl acetate (3×20 mL). The combined
extracts were dried over anhydrous sodium sulfate and
evaporated, and the residue was purified by column
chromatography using hexane–ethyl acetate (1:1) as
eluent.
3-(2,4-Dioxo-1,2,3,4-tetrahydropyrimidin-1-yl-
methyl)-4-methoxybenzaldehyde (VII). Yield 56%,
white crystals, mp 192–194°C. IR spectrum, ν, cm–1:
3041, 2840 (C–H), 1727, 1674 (C=O), 1598 (C=C),
1
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
(XIIa). Yield 63%, yellow crystals, mp 168–170°C. IR
spectrum, ν, cm–1: 3423 (O–H), 3051 (C–H), 1634
817 (δC–H). H NMR spectrum (DMSO-d6), δ, ppm:
3.94 s (3H, OCH3), 4.86 s (2H, CH2), 5.61 d (1H, 5′-H,
J = 8.0 Hz), 7.25 d (1H, 5-H, J = 8.0 Hz), 7.60 d (1H,
2-H, J = 2.0 Hz), 7.69 d (1H, 6′-H, J = 8.0 Hz),
7.90 d.d (1H, 6-H, J = 2.0, 8.0 Hz), 9.87 s (1H, CHO),
11.31 s (1H, 3′-H). 13C NMR spectrum (DMSO-d6), δC,
ppm: 101.0, 111.3, 125.3, 128.8, 129.2, 132.5, 146.1,
150.9, 161.8, 163.7, 191.3. Found: m/z 261.08698
[M + H]+. C13H13N2O4. Calculated: M + H 261.08747.
1
(C=O), 1588–1601 (C=C), 838 (δC–H). H NMR
spectrum (CDCl3), δ, ppm: 3.87 s (3H, OCH3), 5.84 s
(2H, CH2), 6.95 d (2H, 3-H, 5-H, J = 8.5 Hz), 6.99 d
(1H, 3′-H, J = 8.5 Hz), 7.38 m (1H, 5″-H), 7.43 m (4H,
α-H, 4′-H, 6″-H, 7″-H), 7.59 d (2H, 2-H, 6-H, J =
8.5 Hz), 7.87 d (1H, β-H, J = 15.5 Hz), 7.89 d (1H,
6′-H, J = 2.0 Hz), 8.08 d (1H, 4″-H, J = 8.5 Hz).
13C NMR spectrum (CDCl3), δC, ppm: 51.7, 55.5,
109.6, 114.6, 117.0, 119.3, 120.1, 120.2, 124.1, 124.9,
127.1, 127.7, 130.8, 132.7, 135.4, 146.1, 146.3, 162.3,
163.6, 193.3. Found: m/z 386.14992 [M + H]+.
C23H20N3O3. Calculated: M + H 386.15038.
4-Methoxy-3-(5-methyl-2,4-dioxo-1,2,3,4-tetra-
hydropyrimidin-1-ylmethyl)benzaldehyde (VIII).
Yield 55%, white crystals, mp 201–203°C. IR spec-
trum, ν, cm–1: 3154, 2836 (C–H), 1684 (C=O), 1595
1
(C=C), 813 (δC–H). H NMR spectrum (DMSO-d6), δ,
ppm: 1.79 s (3H, CH3), 3.94 s (3H, OCH3), 4.82 s (2H,
CH2), 7.25 d (1H, 5-H, J = 8.5 Hz), 7.55 m (2H, 2-H,
6′-H), 7.90 d.d (1H, 6-H, J = 2.0, 8.5 Hz), 9.86 s (1H,
CHO), 11.32 s (1H, 3′-H). 13C NMR spectrum
(DMSO-d6), δ, ppm: 11.9, 56.2, 108.7, 111.3, 125.4,
128.3, 129.2, 132.3, 141.7, 150.9, 161.7, 164.3, 191.4.
Found: m/z 275.10263 [M + H]+. C14H15N2O4. Calcu-
lated: M + H 275.10308.
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-(3-methoxyphenyl)prop-2-en-1-one
(XIIb). Yield 65%, yellow crystals, mp 130–132°C. IR
spectrum, ν, cm–1: 3421 (O–H), 3064 (C–H), 1645
1
(C=O), 1575 (C=C), 826 (δC–H). H NMR spectrum
(CDCl3), δ, ppm: 3.88 s (3H, OCH3), 5.84 s (2H, CH2),
7.00 d (2H, 4-H, 3′-H, J = 8.5 Hz), 7.13 d (1H, 2-H,
J = 2.0 Hz), 7.22 d (1H, 6-H, J = 8.5 Hz), 7.36 m (2H,
5-H, 5″-H), 7.44 m (3H, 4′-H, 6″-H, 7″-H), 7.49 d (1H,
α-H, J = 15.5 Hz), 7.85 d (1H, β-H, J = 15.5 Hz),
7.88 d (1H, 6′-H, J = 2.0 Hz), 8.08 d (1H, 4″-H, J =
8.5 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 51.7,
55.5, 109.6, 113.1, 116.9, 119.4, 119.5, 119.9, 120.0,
120.2, 124.2, 125.1, 127.7, 129.0, 130.1, 132.7, 135.6,
135.7, 146.2, 146.3, 160.0, 163.6, 193.3. Found:
m/z 386.14992 [M + H]+. C23H20N3O3. Calculated:
M + H 386.15045.
Piperazine derivatives IX–XI (general proce-
dure). A mixture of 10.0 mmol of 1-methylpiperazine,
1-ethylpiperazine, or 1-phenylpiperazine, 2.07 g
(15 mmol) of potassium carbonate, 1.84 g (10 mmol)
of 3-(chloromethyl)-4-methoxybenzaldehyde (VI), and
238 mg (1 mmol) of butyl(triethyl)ammonium bromide
in 25 mL of anhydrous dimethylformamide was stirred
for 10 min at 70°C under microwave irradiation
(300 W). The mixture was concentrated under reduced
pressure, and the residue was diluted with chloroform
(60 mL), and washed with distilled water (4×60 mL).
The organic phase was separated, dried over anhydrous
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-(4-isopropylphenyl)prop-2-en-1-one
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 12 2014

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF CHALCONES
1771
(XIIc). Yield 69%, yellow crystals, mp 135–137°C. IR
spectrum, ν, cm–1: 3432 (O–H), 3062 (C–H), 1637
(C=O), 1562–1606 (C=C), 838 (δC–H). H NMR
1-one (XIIf). Yield 60%, white crystals, mp 148–
150°C. IR spectrum, ν, cm–1: 3444 (O–H), 2962
(C–H), 1657 (C=O), 1570 (C=C), 825 (δ C–H).
1H NMR spectrum (CDCl3), δ, ppm: 3.92 s (3H,
OCH3), 3.95 s (6H, OCH3), 5.84 s (2H, CH2), 6.85 s
(2H, 2-H, 6-H), 7.01 d (1H, 3′-H, J = 8.5 Hz), 7.40 m
(5H, α-H, 4′-H, 5″-H, 6″-H, 7″-H), 7.81 d (1H, β-H,
J = 155 Hz), 7.85 s (1H, 6′-H), 8.06 d (1H, 4″-H, J =
8.5 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 51.6,
56.4, 61.4, 106.2, 109.5, 118.8, 119.4, 120.0, 120.1,
124.1, 125.1, 127.7, 128.9, 132.6, 132.7, 135.4,
146.3, 146.4, 153.5, 163.2, 163.5, 193.1. Found:
m/z 446.17105 [M + H]+. C25H24N3O5. Calculated:
M + H 446.17158.
1
spectrum (CDCl3), δ, ppm: 1.27 d [6H, CH(CH3)2, J =
7.0 Hz], 2.96 m [1H, CH(CH3)2], 5.81 s (2H, CH2),
6.99 d (1H, 3′-H, J = 8.5 Hz), 7.30 d (1H, 5-H, J =
8.5 Hz), 7.37 m (1H, 5″-H), 7.43 m (3H, 4′-H, 6″-H,
7″-H), 7.48 d (1H, α-H, J = 15.5 Hz), 7.56 d (2H, 2-H,
6-H, J = 8.5 Hz), 7.88 d (1H, β-H, J = 15.5 Hz), 7.89 d
(1H, 6′-H, J = 2.0 Hz), 8.09 d (1H, 4″-H, J = 8.0 Hz).
13C NMR spectrum (CDCl3), δC, ppm: 23.7, 34.2, 51.7,
109.6, 118.6, 119.4, 120.1, 120.2, 124.1, 125.0, 127.2,
127.7, 129.0, 131.9, 132.6, 135.4, 146.3, 146.4, 152.8,
163.6, 193.4. Found: m/z 398.18630 [M + H]+.
C25H24N3O2. Calculated: M + H 398.18681.
(E)-1-(5-{3-[5-(1H-Benzotriazol-1-ylmethyl)-2-
hydroxyphenyl]-3-oxoprop-1-en-1-yl}-2-methoxy-
benzyl)pyrimidine-2,4(1H,3H)-dione (XIIg). Yield
57%, yellow crystals, mp 263–265°C. IR spectrum, ν,
cm–1: 3447 (O–H, N–H), 3033 (C–H), 1640–1703
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-(4-methylphenyl)prop-2-en-1-one
(XIId). Yield 61%, white crystals, mp 175–177°C. IR
spectrum, ν, cm–1: 3445 (O–H), 3102 (C–H), 1636
1
1
(C=O), 1569–1610 (C=C), 838 (δC–H). H NMR
(C=O), 1564–1606 (C=C), 838 (δC–H). H NMR
spectrum (CDCl3), δ, ppm: 3.96 s (3H, OCH3), 4.93 s
(2H, CH2), 5.69 d (1H, 5-H, J = 7.5 Hz), 5.88 s (2H,
CH2), 7.00 d (2H, 3′-H, 5-H, J = 8.5 Hz), 7.40 m (1H,
5″-H), 7.47 m (4H, 4′-H, 6″-H, 6′′′-H, 7″-H), 7.54 d
(1H, α-H, J = 15.5 Hz), 7.63 d.d (1H, 6-H, J = 2.0,
8.5 Hz), 7.81 d (1H, 2-H, J = 2.0 Hz), 7.86 d (1H, β-H,
J = 15.5 Hz), 8.05 s (1H, 6′-H), 8.07 d (1H, 4″-H, J =
8.5 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 47.2,
51.4, 55.5, 101.3, 109.7, 111.0, 118.0, 118.9, 119.3,
119.9, 123.7, 124.3, 127.2, 127.7, 129.3, 131.4, 131.7,
135.3, 145.2, 145.3, 145.6, 151.3, 159.8, 163.0, 164.4,
193.3. Found: m/z 510.17720 [M + H]+. C28H24N5O5.
Calculated: M + H 510.17768.
spectrum (CDCl3), δ, ppm: 2.41 s (3H, CH3), 5.84 s
(2H, CH2), 6.99 d (1H, 3′-H, J = 8.0 Hz), 7.24 d (2H,
3-H, 5-H, J = 8.0 Hz), 7.37 m (1H, 5″-H), 7.43 m (3H,
4′-H, 6″-H, 7″-H), 7.48 d (1H, α-H, J = 15.5 Hz),
7.53 d (2H, 2-H, 6-H, J = 8.0 Hz), 7.87 d (1H, β-H, J =
15.5 Hz), 7.89 s (1H, 6′-H), 8.08 d (1H, 4″-H, J =
8.5 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 21.6,
51.7, 109.5, 118.4, 119.4, 120.1, 120.2, 124.1, 125.0,
127.6, 131.6, 132.7, 135.4, 135.5, 141.9, 146.3, 146.4,
152.8, 163.6, 193.4. Found: m/z 370.15500 [M + H]+.
C23H20N3O2. Calculated: M + H 370.15547.
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-
2-en-1-one (XIIe). Yield 37%, yellow crystals,
mp 126–128°C. IR spectrum, ν, cm–1: 3440 (O–H),
3050 (C–H), 1639 (C=O), 1568 (C=C), 834 (δC–H).
1H NMR spectrum (CDCl3), δ, ppm: 3.96 s (3H,
OCH3), 5.84 s (2H, CH2), 6.89 d (1H, 3-H, J = 8.5 Hz),
6.99 d (1H, 3′-H, J = 8.5 Hz), 7.14 d.d (1H, 2-H, J =
2.0, 8.5 Hz), 7.27 s (1H, 6-H), 7.37 m (2H, α-H, 5″-H),
7.44 m (3H, 4′-H, 6″-H, 7″-H), 7.82 d (1H, β-H, J =
15.5 Hz), 7.87 d (1H, 6′-H, J = 2.0 Hz), 8.09 d (1H,
4″-H, J = 8.5 Hz). 13C NMR spectrum (CDCl3), δC,
ppm: 51.7, 56.1, 109.6, 110.7, 113.3, 117.6, 119.4,
120.1, 120.2, 123.4, 124.2, 125.0, 127.7, 128.0, 131.3,
132.6, 135.3, 146.1, 146.2, 149.6, 163.6, 193.3. Found:
m/z 402.14483 [M + H]+. C23H20N3O4. Calculated:
M + H 402.14534.
(E)-1-(5-{3-[5-(1H-Benzotriazol-1-ylmethyl)-2-
hydroxyphenyl]-3-oxoprop-1-en-1-yl}-2-methoxy-
benzyl)-5-methylpyrimidine-2,4(1H,3H)-dione
(XIIh). Yield 56%, yellow crystals, mp 168–170°C. IR
spectrum, ν, cm–1: 3446 (O–H, N–H), 3035 (C–H),
1639–1681 (C=O), 1589–1612 (C=C), 835 (δC–H).
1H NMR spectrum (CDCl3), δ, ppm: 1.90 s (3H, CH3),
3.95 s (3H, OCH3), 4.92 s (2H, CH2), 5.86 s (2H,
CH2), 6.98 d (1H, 5-H, J = 8.0 Hz), 7.00 d (1H, 3′-H,
J = 8.0 Hz), 7.38 m (1H, 5″-H), 7.46 m (4H, 4′-H,
6″-H, 6′′′-H, 7″-H), 7.51 d (1H, α-H, J = 15.5 Hz),
7.59 d.d (1H, 6-H, J = 2.0, 8.0 Hz), 7.76 d (1H, 2-H,
J = 2 Hz), 7.85 d (1H, β-H, J = 15.5 Hz), 8.02 d (1H,
6′-H, J = 2.0 Hz), 8.08 d (1H, 4″-H, J = 8.0 Hz).
13C NMR spectrum (CDCl3), δC, ppm: 12.3, 46.6, 51.6,
55.8, 109.7, 110.4, 111.0, 118.2, 119.1, 119.9, 120.1,
124.3, 124.5, 125.1, 127.4, 127.7, 129.4, 131.0, 131.8,
132.6, 135.5, 140.9, 145.3, 146.0, 151.4, 159.7, 162.7,
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 12 2014

CHINH et al.
1772
164.2, 192.6. Found: m/z 524.19285 [M + H]+.
C29H26N5O5. Calculated: M + H 524.19336.
(2H, CH2), 6.83 t (1H, p-H, J = 8.5 Hz), 6.94 d (3H,
5-H, o-H, J = 8.5 Hz), 6.98 d (1H, 3′-H, J = 8.5 Hz),
7.23 m (2H, m-H), 7.34 m (1H, 5″-H), 7.41 m (3H,
4′-H, 6″-H, 7″-H), 7.48 d (1H, α-H, J = 15.5 Hz),
7.56 d.d (1H, 6-H, J = 2.0, 8.5 Hz), 7.79 s (1H, 2-H),
7.91 d (1H, β-H, J = 15.5 Hz), 7.97 s (1H, 6′-H),
8.05 d (1H, 4″-H, J = 8.5 Hz). 13C NMR spectrum
(CDCl3), δC, ppm: 49.1, 51.7, 53.1, 55.6, 55.7, 109.6,
110.8, 116.1, 117.3, 119.3, 119.7, 120.1, 124.0, 125.0,
126.9, 127.6, 129.1, 129.8, 131.3, 132.6, 135.3, 146.3,
151.3, 160.5, 163.6, 193.3. Found: m/z 560.26562
[M + H]+. C34H34N5O3. Calculated: M + H 560.26619.
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-[4-methoxy-3-(4-methylpiperazin-
1-ylmethyl)phenyl]prop-2-en-1-one (XIIi). Yield
52%, yellow crystals, mp 196–198°C. IR spectrum, ν,
cm–1: 3444 (O–H), 2938 (C–H), 1637 (C=O), 1557–
1
1600 (C=C), 831 (δC–H). H NMR spectrum (CDCl3),
δ, ppm: 2.17 s (3H, NCH3), 2.55 s (4H, 3′′′-H, 5′′′-H),
2.61 s (4H, 2′′′-H, 6′′′-H), 3.90 s (3H, OCH3), 3.62 s
(2H, CH2), 5.85 s (2H, CH2), 6.92 d (1H, 5-H, J =
8.5 Hz), 6.99 d (1H, 3′-H, J = 8.5 Hz), 7.37 m (1H,
5″-H), 7.43 m (3H, 4′-H, 6″-H, 7″-H), 7.47 d (1H, α-H,
J = 15.5 Hz), 7.55 d.d (1H, 6-H, J = 2.0, 8.5 Hz),
7.74 s (1H, 2-H), 7.90 d (1H, β-H, J = 15.5 Hz), 7.98 d
(1H, 6′-H, J = 2.0 Hz), 8.08 d (1H, 4″-H, J = 8.5 Hz).
13C NMR spectrum (CDCl3), δ, ppm: 45.9 (NCH3),
51.8, 52.9, 55.0, 55.5, 55.7, 109.6, 110.8, 117.2, 119.3,
120.2, 124.1, 124.9, 126.8, 126.9, 127.6, 129.1, 129.6,
131.3, 132.6, 135.3, 146.4, 146.5, 160.5, 163.4, 193.3.
Found: m/z 498.24997 [M + H]+. C29H32N5O3. Calcu-
lated: M + H 498.25048.
(E)-1-[2-Hydroxy-5-(1H-imidazol-1-ylmethyl)-
phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one
(XIIIa). Yield 54%, yellow crystals, mp 163–165°C.
IR spectrum, ν, cm–1: 3445 (O–H), 3096 (C–H), 1638
1
(C=O), 1570–1604 (C=C), 836 (δC–H). H NMR
spectrum (CDCl3), δ, ppm: 3.86 s (3H, OCH3), 5.12 s
(2H, CH2), 6.94 d.d (3H, 3-H, 5-H, 5″-H, J = 2.0,
8.5 Hz), 7.01 d (1H, 3′-H, J = 8.5 Hz), 7.12 s (1H,
4″-H), 7.30 d.d (1H, 4′-H, J = 2.5, 8.5 Hz), 7.41 d (1H,
α-H, J = 15.5 Hz), 7.61 d.d (3H, 2-H, 2″-H, 6-H, J =
2.5, 8.5 Hz), 7.69 d (1H, 6′-H, J = 2.0 Hz), 7.90 d (1H,
β-H, J = 15.5 Hz). 13C NMR spectrum (CDCl3), δC,
ppm: 50.3, 55.5, 114.6, 117.0, 119.2, 119.5, 119.8,
120.1, 126.2, 127.1, 128.5, 130.7, 130.8, 135.2,
135.7, 137.3, 146.2, 163.8, 164.7, 193.2. Found:
m/z 337.15467 [M + H]+. C20H21N2O3. Calculated:
M + H 337.15501.
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-[3-(4-ethylpiperazin-1-ylmethyl)-4-
methoxyphenyl]prop-2-en-1-one (XIIj). Yield 51%,
yellow crystals, mp 184–186°C. IR spectrum, ν, cm–1:
3431 (O–H), 2933 (C–H), 1636 (C=O), 1589–1603
1
(C=C), 834 (δC–H). H NMR spectrum (CDCl3), δ,
ppm: 1.10 s (3H, CH2CH3), 2.46 m (2H, CH2CH3),
2.62 s (8H, 2′′′-H, 3′′′-H, 5′′′-H, 6′′′-H), 3.63 s (2H,
CH2), 3.89 s (3H, OCH3), 5.85 s (2H, CH2), 6.92 d
(1H, 5-H, J = 8.5 Hz), 6.98 d (1H, 3′-H, J = 8.5 Hz),
7.36 m (1H, 5″-H), 7.43 m (3H, 4′-H, 6″-H, 7″-H),
7.47 d (1H, α-H, J = 15.5 Hz), 7.55 d.d (1H, 6-H, J =
2.0, 8.5 Hz), 7.73 s (1H, 2-H), 7.90 d (1H, β-H, J =
15.5 Hz), 7.97 s (1H, 6′-H), 8.08 d (1H, 4″-H, J =
8.5 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 11.8,
21.7, 52.2, 52.7, 52.9, 55.6, 109.6, 110.7, 117.1, 119.4,
120.1, 124.1, 124.9, 126.9, 126.8, 127.6, 129.1, 129.6,
131.3, 132.6, 135.3, 146.3, 146.5, 160.5, 163.5, 193.3.
Found: m/z 512.26562 [M + H]+. C30H34N5O3. Calcu-
lated: M + H 512.26613.
(E)-1-[2-Hydroxy-5-(1H-imidazol-1-ylmethyl)-
phenyl]-3-(3-methoxyphenyl)prop-2-en-1-one
(XIIIb). Yield 55%, yellow crystals, mp 96–98°C. IR
spectrum, ν, cm–1: 3418 (O–H), 3118 (C–H), 1639
1
(C=O), 1563–1588 (C=C), 840 (δC–H). H NMR
spectrum (CDCl3), δ, ppm: 3.87 s (3H, OCH3), 5.12 s
(2H, CH2), 6.93 s (1H, 5″-H), 7.00 d.d (1H, 4-H, J =
4.0, 8.5 Hz), 7.03 d (1H, 3′-H, J = 8.5 Hz), 7.11 s (1H,
4″-H), 7.15 s (1H, 2-H), 7.26 d (1H, 6-H, J = 8.5 Hz),
7.31 d.d (1H, 4′-H, J = 2.0, 8.5 Hz), 7.36 t (1H, 5-H,
J = 8.5 Hz), 7.51 d (1H, α-H, J = 15.5 Hz), 7.56 s (1H,
2″-H), 7.68 d (1H, 6′-H, J = 2.0 Hz), 7.88 d (1H, β-H,
J = 15.5 Hz), 12.84 s (1H, OH). 13C NMR spectrum
(CDCl3), δC, ppm: 50.1, 55.4, 113.9, 116.8, 119.0,
119.5, 119.8, 119.9, 121.3, 126.4, 128.5, 130.0, 130.1,
135.3, 135.7, 137.2, 146.1, 160.0, 163.5, 193.3. Found:
m/z 337.15467 [M + H]+. C20H21N2O3. Calculated:
M + H 337.15512.
(E)-1-[5-(1H-Benzotriazol-1-ylmethyl)-2-hy-
droxyphenyl]-3-[4-methoxy-3-(4-phenylpiperazin-1-
ylmethyl)phenyl]prop-2-en-1-one (XIIk). Yield 45%,
yellow crystals, mp 202–203°C. IR spectrum, ν, cm–1:
3444 (O–H), 2909 (C–H), 1637 (C=O), 1558–1601
1
(C=C), 832 (δC–H). H NMR spectrum (CDCl3), δ,
(E)-1-[2-Hydroxy-5-(1H-imidazol-1-ylmethyl)-
phenyl]-3-(4-isopropylphenyl)prop-2-en-1-one
(XIIIc). Yield 63%, yellow crystals, mp 140–142°C.
ppm: 2.73 m (4H, 2′′′-H, 6′′′-H), 3.27 m (4H, 3′′′-H,
5′′′-H), 3.68 s (2H, CH2), 3.91 s (3H, OCH3), 5.81 s
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SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF CHALCONES
1773
1
IR spectrum, ν, cm–1: 3447 (O–H), 3095 (C–H), 1643
(C=O), 1579 (C=C), 826 (δC–H). H NMR spectrum
827 (δC–H). H NMR spectrum (CDCl3), δ, ppm:
3.90 s (3H, OCH3), 4.85 s (2H, CH2), 5.18 s (2H,
CH2), 5.58 d.d (1H, 5′′′-H, J = 2.0, 8.0 Hz), 6.94 s (1H,
5″-H), 6.99 d (1H, 3′-H, J = 8.5 Hz), 7.18 d (1H, 5′-H,
J = 8.5 Hz), 7.26 s (1H, 4″-H), 7.45 d.d (1H, 4′-H, J =
2.0, 8.5 Hz), 7.62 d (1H, 2″-H, J = 2.0 Hz), 7.65 d (1H,
6′′′-H, J = 8.0 Hz), 7.80 d (1H, α-H, J = 15.5 Hz),
7.82 d (1H, β-H, J = 15.5 Hz), 7.84 s (1H, 2-H),
7.92 d.d (1H, 6-H, J = 2.0, 8.5 Hz), 8.15 d (1H, 6′-H,
J = 2.0 Hz). 13C NMR spectrum (CDCl3), δC, ppm:
46.8, 48.8, 55.9, 100.8, 111.6, 118.1, 119.3, 119.7,
120.9, 124.8, 126.8, 128.3, 128.6, 130.0, 130.3, 130.7,
135.4, 137.1, 144.7, 145.9, 150.9, 159.5, 160.9, 163.8,
192.9. Found: m/z 461.18195 [M + H]+. C25H25N4O5.
Calculated: M + H 461.18211.
1
(CDCl3), δ, ppm: 1.28 d [6H, CH(CH3)2, J = 7.0 Hz],
2.96 m [1H, CH(CH3)2], 5.12 s (2H, CH2), 6.93 s (1H,
5″-H), 7.02 d (1H, 3′-H, J = 8.0 Hz), 7.12 s (1H, 4″-H),
7.30 br.s (3H, 3-H, 4′-H, 5-H), 7.51 d (1H, α-H, J =
15.5 Hz), 7.59 s (2H, 2-H, 6-H), 7.62 s (1H, 2″-H),
7.70 s (1H, 6′-H), 7.92 d (1H, β-H, J = 15.5 Hz).
13C NMR spectrum (CDCl3), δC, ppm: 23.7, 34.2, 50.3,
119.1, 119.5, 120.0, 126.3, 127.2, 128.6, 129.0, 129.8,
132.0, 135.3, 137.3, 146.4, 152.8, 163.5, 193.4. Found:
m/z 349.19105 [M + H]+. C22H25N2O. Calculated:
M + H 349.19106.
(E)-1-[2-Hydroxy-5-(1H-imidazol-1-ylmethyl)-
phenyl]-3-(4-methylphenyl)prop-2-en-1-one
(XIIId). Yield 62%, yellow crystals, mp 174–176°C.
IR spectrum, ν, cm–1: 3442 (O–H), 3095 (C–H), 1641
(E)-1-(5-{3-[2-Hydroxy-5-(1H-imidazol-1-yl-
methyl)phenyl]-3-oxoprop-1-en-1-yl}-2-methoxy-
benzyl)-5-methylpyrimidine-2,4(1H,3H)-dione
(XIIIg). Yield 49%, yellow crystals, mp 209–211°C.
IR spectrum, ν, cm–1: 3448 (O–H, N–H), 1641–1685
(C=O), 1567–1606 (C=C), 832 (δC–H). 1H NMR spec-
trum (CDCl3), δ, ppm: 1.89 s (3H, CH3), 3.95 s (3H,
OCH3), 4.91 s (2H, CH2), 5.19 s (2H, CH2), 6.98 s
(1H, 4″-H), 7.00 m (2H, 3′-H, 5-H), 7.17 s (1H,
5″-H),7.37 d.d (1H, 6-H, J = 2.0, 8.5 Hz), 7.40 s (1H,
2-H), 7.46 d (1H, α-H, J = 15.5 Hz), 7.60 d.d (1H,
4′-H, J = 2.0, 8.5 Hz), 7.74 s (1H, 6′′′-H), 7.78 s (1H,
2″-H), 7.85 d (1H, β-H, J = 15.5 Hz), 7.90 s (1H, 6H),
12.9 s (1H, OH). 13C NMR spectrum (CDCl3), δC,
ppm: 12.4, 46.1, 50.2, 55.9, 110.3, 111.1, 118.0, 119.1,
119.3, 120.0, 125.1, 127.3, 128.7, 129.0, 130.0. 130.2,
131.8, 135.3, 137.2, 140.6, 145.4, 151.5, 159.7, 163.3,
164.8, 193.1. Found: m/z 475.19760 [M + H]+.
C26H27N4O5. Calculated: M + H 475.19791.
1
(C=O), 1577–1606 (C=C), 838 (δC–H). H NMR spec-
trum (CDCl3), δ, ppm: 2.40 s (3H, CH3), 5.11 s (2H,
CH2), 6.92 s (1H, 4″-H), 7.01 d (1H, 3′-H, J = 8.0 Hz),
7.11 s (1H, 5″-H), 7.55 d (2H, 3-H, 5-H, J = 8.0 Hz),
7.59 s (1H, 2″-H), 7.70 d (1H, 6′-H, J = 2.0 Hz), 7.90 d
(1H, β-H, J = 15.5 Hz), 12.89 s (1H, OH). 13C NMR
spectrum (CDCl3), δC, ppm: 21.6, 50.2, 118.4, 119.0,
119.5, 119.9, 126.2, 128.5, 128.8, 129.8, 131.6,
135.2, 137.2, 141.9, 146.4, 163.4, 193.3. Found:
m/z 321.15975 [M + H]+. C20H21N2O2. Calculated:
M + H 321.16000.
(E)-1-[2-Hydroxy-5-(1H-imidazol-1-ylmethyl)-
phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-
1-one (XIIIe). Yield 39%, yellow crystals, mp 188–
190°C. IR spectrum, ν, cm–1: 3448 (O–H), 3000
(C–H), 1637 (C=O), 1561–1611 (C=C), 827 (δC–H).
1H NMR spectrum (CDCl3), δ, ppm: 3.86 s (1H,
OCH3), 5.17 s (1H, CH2), 6.48 d (1H, 3′-H, J =
8.5 Hz), 6.91 s (1H, 5″-H), 7.03 d (1H, 5-H, J =
8.5 Hz), 7.24 s (1H, 4′-H), 7.30 d.d (1H, 6-H, J = 2.0,
8.5 Hz), 7.37 d (1H, 2-H, J = 2.0 Hz), 7.45 d.d (1H,
4′-H, J = 2.0, 8.5 Hz), 7.60 m (3H, α-H, β-H, 2″-H),
8.25 d (1H, 6′-H, J = 2.0 Hz). 13C NMR spectrum
(CDCl3), δC, ppm: 48.8, 55.7, 111.9, 114.8, 118.1,
118.9, 119.3, 120.7, 122.8, 127.3, 128.4, 128.7, 130.2,
135.5, 137.1, 145.6, 146.8, 150.8, 161.2, 193.0. Found:
m/z 353.14958 [M + H]+. C20H21N2O4. Calculated:
M + H 353.15001.
Antimicrobial and antifungal activity of com-
pounds XII and XIII. The antimicrobial and anti-
fungal activity of chalcones XII and XIII was assessed
by the microbroth dilution method [14, 15]. Com-
pounds were assumed to be inactive if the minimum
inhibitory concentration (MIC) exceeded 50 μg/mL.
Chalcones XII and XIII showed no activity against
mycelial fungi and yeasts. Benzotriazole derivatives
XIIi–XIIk were active against gram-positive bacteria
Bacillus subtillis and Staphylococcus aureus (MIC 25
and 12.5, 12.5 and 12.5, and 12.5 and 12.5 μg/mL,
respectively). Imidazolylmethyl derivatives XIII were
found to exhibit considerably higher antimicrobial
activity which also depended on the nature and posi-
tion of substituents in the aldehyde component. Chal-
cone XIIIb having a methoxy group in position 3 of
the ring B was active against both gram-negative and
(E)-1-(5-{3-[2-Hydroxy-5-(1H-imidazol-1-yl-
methyl)phenyl]-3-oxoprop-1-en-1-yl}-2-metoxyben-
zyl)pyrimidine-2,4(1H,3H)-dione (XIIIf). Yield 49%,
yellow crystals, mp 201–203°C. IR spectrum, ν, cm–1:
3447 (O–H, N–H), 1634 (C=O), 1639–1716 (C=C),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 50 No. 12 2014

CHINH et al.
1774
5. Yañez, E.C., Sánchez, A.C., Becerra, J.M.S.,
Muchowski, J.M., and Almanza, R.C., Rev. Soc. Quím.
Méx., 2004, vol. 48, p. 49.
6. Graebin, C.S., Uchoa, F.D., Bernardes, L.S.C.,
Campo, V.L., Carvalho, I., and Eifler-Lima, V.L., Anti-
Infect. Agents Med. Chem., 2009, vol. 8, p. 345.
7. Ohlan, C.R., Ohlan, S., Judge, V., Narang, R.,
Ahuja, M., and Narasimhan, B., Arkivoc, 2007,
part (xiv), p. 172.
8. Talaviya, S. and Majmudar, F., Int. J. Pharm. Pharm.
Sci., 2012, vol. 4, p. 4.
gram-positive bacteria Pseudomonas aeruginosa,
Bacillus subtillis, and Staphylococcus aureus (MIC 50,
12.5, and 25 μg/mL, respectively), whereas its 4-me-
thoxy analog XIIIa inhibited the growth of only gram-
negative Pseudomonas aeruginosa (MIC 25 μg/mL).
The presence of an alkyl group in position 4 increased
the activity of compounds XIIIc and XIIId against
gram-positive bacteria Bacillus subtillis and Staphylo-
coccus aureus (MIC 25, 12.5 and 25, 50 μg/mL,
respectively).
This study was performed under financial support
by the Vietnam Science and Technology Foundation
(NAFOSTED; project no. 104.01.67.09).
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