Synthesis of hydrazone derivatives of benzofuran and their antibacterial and antifungal activity

Article abstract of DOI:10.1134/S1070363217090183

A series of benzofuran hydrazones 6a–6n were synthesized from benzofuran aldehyde and substituted aromatic hydrazides 5a–5n. Structures of all compounds were confimed by IR, ¹H and ¹³C NMR, and Mass spectral data. These compounds wer

Full text of DOI:10.1134/S1070363217090183

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 9, pp. 2021–2026. © Pleiades Publishing, Ltd., 2017.
Synthesis of Hydrazone Derivatives of Benzofuran
1
and Their Antibacterial and Antifungal Activity
a
a
a
N. J. P. Subhashini *, P. Janaki , and B. Bhadraiah
Department of Chemistry, University College of Science, Osmania University, Hyderabad, 500007 India
*
e-mail: njsubhashini@yahoo.co.in
Received December 31, 2016
Abstract—A series of benzofuran hydrazones 6a–6n were synthesized from benzofuran aldehyde and
1
13
substituted aromatic hydrazides 5a–5n. Structures of all compounds were confimed by IR, H and C NMR,
and Mass spectral data. These compounds were evaluated for their antibacterial activity against gram-negative
bacteria (Escherichia coli, –ve), gram-positive bacteria (Bacillus Subtillis, +ve), and antifungal activity against
Candida albicans. All compounds demonstrated considerable activity against bacteria and fungi.
Keywords: benzofuran, hydrazide, hydrozone, benzofuran aldehyde, antibacterial and antifungal activities
DOI: 10.1134/S1070363217090183
INTRODUCTION
(Escherichia coli, –ve), gram-positive bacteria
Bacillus Subtillis, +ve) and antifungal activity against
Candida albicans (see table) and demonstrated
distinctive potential, particularly compounds 6a–6c,
6g–6i, and 6k.
(
Benzofuran derivatives such as Cicerfuran and
Conocarpan [1, 2] display potent biological properties
including antimicrobial [3], anti-inflammatory [4, 5],
anticonvulsant [6–7], antitumor [8], anti-HIV [9],
antidiabetic [10], antitubercular [11], antihyperglycemic
Antifungal activity of synthesized compounds 6a–
6
n was tested against Candida albicans by the poison
[
[
12], analgesic [13], antiparasitic [14], and antioxidant
15].
plate technique at a concentration of 100 µL (see the
table). Amphoteracin-B (10 µL) was used as the
standard control.
Similarly, aroyl hydrazone containing the azomethine
NHN=CH protons constitute the compounds im-
–
portant in new drugs development [16]. Some widely
used antibacterial drugs such as furacilin and ftivazide
contain this group (Scheme 1).
EXPERIMENTAL
All chemicals were of commercially pure grade.
TLC was carried out on aluminium plates coated with
silica gel (SiO ; Merck 60 F254). Melting points were
determined on a Stuart SMP3 melting point apparatus.
IR spectra (KBr pellets) were recorded on a Shimadzu
FTIR 8400 S spectrophotometer. NMR spectra were
measured on a Bruker Avance-400 spectrometer in
Herein, we report synthesis, characterization and
biological evaluation of some hydrozone derivatives of
benzofurans.
2
RESULTS AND DISCUSSION
DMSO-d using TMS as the internal standard. Mass
spectra were measured on a Finnigan MAT 1020 mass
spectrometer.
6
Synthetic routs for the target compounds 6a–6n are
summarized in Scheme 2. The structures of products
1
13
6
a–6n were confirmed by their IR, H, C NMR, and
mass spectral data.
Synthesis of 2-iodo-4-methyl-6-nitrophenol (2).
To the stirred solution of compound 1 (10 g,
65.40 mmol) in water (100 mL) was added sodium
bicarbonate (523 mmol) followed by addition of iodine
All synthesized compounds 6a–6n were evaluated
for their antibacterial and antifungal activities. The
antibacterial activity against gram-negative bacteria
(
16.6 g, 65.40 mmol) in small portions within 1 h and
heating at 95°C for 2.5 h. The reaction mixture was
cooled down to room temperature, acidified with 1 N
1
The text was submitted by the authors in English.
2
021

2
022
SUBHASHINI et al.
Scheme 1.
MeO
H
O
N
O
NH2
O N
2
N
O
HO
O
O
O
Cicerfuran
Conocarpan
Furacilin
N
O
NH
OH
OMe
N
Ftivazide
Scheme 2. Synthetic route for the benzofuran-hydrazone derivatives 6a–6n.
Me
Me
I
Me
OH
OH,
TPP, CuI
Morpholine, H O, Pd/C,
2
I2, NaHCO3
OH H O, 95°C, 2.5 h
2
OH
O
1
15°C, 1 h
NO2
NO2
NO2
1
2
3
H
N
O
H N
2
MnO , DCM,
2
R
room temperature, 6 h
R
O
5
a−5n
Me
Me
N NH
7
0vC, EtOH, 4 h
CHO
O
O
NO2
NO2
6
a−6n
4
R = 4-chloro- (a), 4-methoxy- (b), 4-fluoro- (c), 4-bromo- (d), 6-bromo- (e), 5-nitro- (f), 4,6-dichloro- (g), 3,6-difluoro- (h),
,4,5-trimethoxy- (i), 4-hydroxy- (j), 3,5-dichloro- (k), 4-methylsulphonyl- (l), H (m), 6-iodo- (n).
3
HCl and then extracted with diethyl ether (3×50 mL).
The organic layer was separated and washed with
water, brine solution, dried over sodium sulphate,
filtered, and evaporated to obtain compound 2 as a
yellow solid.
with 10% Pd/C (0.3 g), triphenylphosphine (0.23 g,
0.86 mmol), CuI (80 mg, 0.43 mmol), and morpholine
(23 mmol) in water (10 mL) was stirred at room
temperature for 1 h under the atmosphere of N2.
Propargyl alcohol (23 mmol) was added to the above
reaction mixture and refluxed for 1 h. The reaction
mixture was cooled down to room temperature, diluted
with ethyl acetate (100 mL) and filtered through cellite
Synthesis of (5-methyl-7-nitrobenzofuran-2-yl)-
methanol (3). A mixture of compound 2 (2 g, 7.16 mmol)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 9 2017

SYNTHESIS OF HYDRAZONE DERIVATIVES OF BENZOFURAN
2023
In vitro antibacterial and antifungal activities of compounds 6a–6n
Zone of inhibition, mm
antibacterial activity
antifungal activity
Compound
E. coli (–ve)
B. Subtillis (+ve)
Candida albicans
concentration c, µL
1
00
200
12
14
15
15
13
17
13
13
19
10
18
14
16
12
100
200
100
12
12
12
11
10
3
200
6
6
a
9
17
28
19
17
22
18
15
3
b
10
19
23
6
c
11
8
9
19
6
d
14
19
6
e
9
8
9
6
f
11
10
9
9
10
6
6
g
15
22
4
10
16
10
12
14
9
h
10
17
10
5
6
i
13
9
9
14
6
j
9
12
8
6
k
10
8
8
No activity
9
9
10
5
6
l
7
6
m
11
9
8
16
11
–
21
14
–
6
n
No activity
13
No activity
No activity
Gentamycin
c = 10 µL)
16
No activity
(
Amphoteracin-B
c = 10 µL)
–
–
–
–
10
No activity
(
bed. The filtrate was washed with water (2×50 mL),
dried over sodium sulphate, filtered and concentrated
to afford compound 3 as a yellow solid.
n-hexane, filtered and dried over vacuo to obtain the
pure compounds 6a–6n. Yields of the products varied
from 80 to 90%.
Synthesis of 5-methyl-7-nitrobenzofuran-2-carbal-
dehyde (4). A mixture of compound 3 (2 g, 9.66 mmol)
2-Iodo-4-methyl-6-nitrophenol (2). Yield 88%,
mp 97–99°C. IR spectrum, ν, cm : 3079, 1537. H
–
1
1
with MnO (67.7 mmol) in dichloromethane (40 mL)
NMR spectrum, δ, ppm: 2.30 s (3H, CH ), 7.98 s (2H,
2
3
1
3
was stirred at room temperature for 6 h. The reaction
mixture was filtered through celite pad and the organic
layer was evaporated to obtain pale yellow solid
compound 4.
Ar-H), 11.20 s (1H, OH). C NMR spectrum, δ, ppm:
19.9, 86.6, 125.0, 131.6, 132.6, 148.0, 151.9. MS, m/z:
–
277.78 [M – H] .
(
5-Methyl-7-nitrobenzofuran-2-yl)methanol (3).
–1
Synthesis of benzofuran hydrazide derivatives
Yield 62%, mp 153–154°C. IR spectrum, ν, cm : 3200,
1585. H NMR spectrum, δ, ppm: 2.10 t (J = 6.6 Hz,
1
6
a–6n. To a solution of 5-methyl-7-nitrobenzofuran-2-
carbaldehyde 5 (1 mmol) and hydrazides 5a–5n
1.2 mmol) in ethanol (10 mL) was added the above
1H, OH), 2.58 s (3H, CH ), 4.85 d (2H, J = 6.8 Hz,
3
(
OCH ), 6.68 s (1H, Ar-H), 7.62 s (1H, Ar-H), 7.98 s
2
1
3
reaction mixture and stirred at 70°C for 4 h. Upon
completion of the reaction, the solvent was evaporated
under vacuo and the residue was triturated with
(1H, Ar-H). C NMR spectrum, δ, ppm: 21.0, 57.8,
103.7, 121.4, 128.1, 132.2, 133.0, 133.1, 145.4, 159.5.
+
MS, m/z: 207.96 [M + H] .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 9 2017

2
024
SUBHASHINI et al.
5
-Methyl-7-nitrobenzofuran-2-carbaldehyde (4).
(1H, Ar-H), 7.59 s (2H, Ar-H), 7.71 s (1H, Ar-H), 7.82–
7.86 m (3H, Ar-H), 7.90 s (1H, Ar-H), 12.4 s (1H,
NH). C NMR spectrum, δ, ppm: 18.67, 99.71, 118.3,
–
1
Yield 78%, mp 179–180°C. IR spectrum, ν, cm :
740, 1524. H NMR spectrum, δ, ppm: 2.51 s (3H, CH ),
.01 s (1H, Ar-H), 8.17 s (1H, Ar-H), 8.28 s (1H, Ar-
H), 9.94 s (1H, CHO). MS, m/z: 206.07 [M + H] .
1
13
1
8
3
121.3, 123.9, 125.4, 125.8, 127.2, 128.9, 130.5, 130.8,
+
130.9, 142.4, 142.5, 142.7, 149.9, 154.5. MS, m/z:
+
+2
4
02.21 [M + H] , 404.12 [M + H] .
(
E)-4-Chloro-N'-[(5-methyl-7-nitrobenzofuran-2-
yl)methylene]benzohydrazide (6a). Yield 80%, mp
(E)-N'-[(5-Methyl-7-nitrobenzofuran-2-yl)-
–
1
1
43–145°C. IR spectrum, ν, cm : 3268, 1742, 1530.
methylene]-3-nitrobenzohydrazide (6f). Yield 87%,
1
–1
H NMR spectrum, δ, ppm: 3.44 s (3H, CH ), 7.56 s
mp 145-147°C. IR spectrum, ν, cm : 3620, 1687,
3
1
(
(
(
1H, Ar-H), 7.62 d (2H, J = 8.54 Hz, Ar-H), 7.94 d
2H, J = 8.54 Hz, Ar-H), 7.97 s (1H, Ar-H), 8.06 s
1523. H NMR spectrum, δ, ppm: 2.53 s (3H, CH ),
3
7.62–7.66 m (1H, Ar-H), 7.85–7.90 m (1H), 8.00 s
(1H, Ar-H), 8.10 s (1H, Ar-H), 8.18 s (1H, Ar-H), 8.38
d (1H, J =7.93 Hz, Ar-H), 8.47–8.49 m (1H, Ar-H),
8.78 s (1H, Ar-H), 12.3 s (1H, NH). MS, m/z: 369.27
13
1H, Ar-H), 8.56 s (1H, Ar-H), 12.2 s (1H, NH).
C
NMR spectrum, δ, ppm: 20.3, 94.0, 109.6, 122.6, 127.6,
1
28.2, 128.5, 129.2, 131.8, 132.7, 133.7, 136.8, 139.2,
+
+
140.9, 145.1, 153.3, 165.2. MS, m/z: 358.18 [M + H] .
[M + H] .
(
E)-4-Methoxy-N'-[(5-methyl-7-nitrobenzofuran-
(E)-2,4-Dichloro-N'-[(5-methyl-7-nitrobenzofuran-
2-yl)methylene]benzohydrazide (6g). Yield 86%, mp
2
-yl)methylene]benzohydrazide (6b). Yield 82%, mp
48–150°C. IR spectrum, ν, cm : 3282, 1654, 1513.
H NMR spectrum, δ, ppm: 3.41 s (3H, CH ), 3.85 s
–1
–1
1
159–161°C. IR spectrum, ν, cm : 3323, 1663, 1525.
1
1
H NMR spectrum, δ, ppm: 2.46 s (3H, CH ), 7.32 s
3
3
(
(
8
3H, OCH ), 7.08 d (2H, J = 9.15Hz, Ar-H), 7.52 s
(1H, Ar-H), 7.55–7.61 m (2H, Ar-H), 7.66 d (1H, J =
8.54 Hz, Ar-H), 7.75 s (1H, Ar-H), 7.82 d (1H, J =
1.83 Hz, Ar-H), 8.36 s (1H, Ar-H), 12.26 s (1H, NH).
3
1H, Ar-H),7.93–7.96 m (3H, Ar-H), 8.06 s (1H, Ar-H),
1
3
.58 s (1H, Ar-H), 12.04 s (1H, NH). C NMR spec-
1
3
trum, δ, ppm: 18.6, 53.2, 108.5, 118.1, 121.9, 126.8,
C NMR spectrum, δ, ppm: 20.3, 109.2, 120.8, 121.6,
1
1
28.9, 129.5, 130.6, 131.5, 134.6, 137.8, 143.3, 145.2,
53.8, 154.5, 162.5, 180.9. MS, m/z: 352.19 [M – H] .
122.5, 127.7, 128.6, 129.1, 131.8, 132.1, 132.7, 133.0,
–
133.7, 136.8, 145.0, 153.6, 163.3. MS, m/z: 392.07
+
[
M + H] .
(
E)-4-Fluoro-N'-[(5-methyl-7-nitrobenzofuran-2-
yl)methylene[benzohydrazide (6c). Yield 84%, mp
(E)-2,5-Difluoro-N'-[(5-methyl-7-nitrobenzofuran-
–1
1
33–135°C. IR spectrum, ν, cm : 3376, 1675, 1524.
2-yl)methylene]benzohydrazide (6h). Yield 81%, mp
1
–1
H NMR spectrum, δ, ppm: 3.43 s (3H, CH ), 7.36–
145–147°C. IR spectrum, ν, cm : 3376, 1669, 1524.
3
1
7
.43 m (3H, Ar-H), 7.56 s (1H, Ar-H), 7.98–8.18 m
H NMR spectrum, δ, ppm: 2.47 s (3H, CH ), 7.36–
3
1
3
(
3H, Ar-H), 8.57 s (1H, Ar-H), 12.17 s (1H, NH). C
7.59 m (2H, Ar-H), 7.61 s (1H, Ar-H), 7.91 s (1H,
Ar-H), 7.99–8.01 m (1H, Ar-H), 8.09 s (1H, Ar-H),
8.42 s (1H, Ar-H), 12.22 s (1H, NH). MS, m/z: 360.20
NMR spectrum, δ, ppm: 21.2, 108.9, 113.4, 115.0, 115.3,
1
1
22.5, 123.6, 129.3, 130.9, 131.7, 132.9, 133.8, 136.5,
44.8, 154.3, 161.3, 161.5. MS, m/z: 342.21 [M + H] .
+
+
[M + H] .
(
E)-4-Bromo-N'-[(5-methyl-7-nitrobenzofuran-2-
(E)-3,4,5-Trimethoxy-N'-[(5-methyl-7-nitrobenzo-
furan-2-yl)methylene]benzohydrazide (6i). Yield
yl)methylene]benzohydrazide (6d). Yield 85%, mp
54–156°C. IR spectrum, ν, cm : 3776, 1665, 1523.
H NMR spectrum, δ, ppm: 3.47 s (3H, CH ), 7.58 s
–1
–1
1
85%, mp 161–163°C. IR spectrum, ν, cm : 3151,
1
1
1654, 1510. H NMR spectrum, δ, ppm: 2.47 s (3H,
3
(
(
1H, Ar-H), 7.78–7.80 m (2H, Ar-H), 7.88–7.91 m
2H, Ar-H), 7.99 s (1H, Ar-H), 8.08 s (1H, Ar-H), 8.57
CH ), 3.74 s (3H, OCH ), 3.87 s (6H, 2OCH ), 7.26 s
3
3
3
(2H, Ar-H), 7.56 s (1H, Ar-H), 7.98 s (1H, Ar-H), 8.07
1
3
13
s (1H, Ar-H), 12.21 s (1H, NH). C NMR spectrum, δ,
s (1H, Ar-H), 8.62 s (1H, Ar-H), 12.00 s (1H, NH). C
ppm: 20.3, 94.03, 109.6, 122.6, 127.6, 128.2, 128.5,
NMR spectrum, δ, ppm: 20.3, 56.1, 60.1, 105.3, 109.2,
1
1
29.2, 131.8, 132.7, 133.7, 136.8, 139.2, 140.9, 145.1,
53.3, 165.2. MS, m/z: 402.21 [M + H] .
121.3, 122.5, 128.0, 129.1, 131.8, 132.7, 133.7, 136.8,
145.0, 152.7, 153.6, 162.7. MS, m/z: 414.22 [M + H] .
+
+
(
E)-2-Bromo-N'-[(5-methyl-7-nitrobenzofuran-2-
(E)-4-Hydroxy-N'-[(5-methyl-7-nitrobenzofuran-
2-yl)methylene]benzohydrazide (6j). Yield 87%, mp
yl)methylene]benzohydrazide (6e). Yield 83%, mp
51–153°C. IR spectrum, ν, cm : 3776, 1665, 1523.
H NMR spectrum, δ, ppm: 2.47 s (3H, CH ), 6.94 s
–1
–1
1
149–151°C. IR spectrum, ν, cm : 3282, 1654, 1513.
1
1
H NMR spectrum, δ, ppm: 2.47 s (3H, CH ), 7.60 s
3
3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 9 2017

SYNTHESIS OF HYDRAZONE DERIVATIVES OF BENZOFURAN
2025
1
13
(
1H, Ar-H), 7.93–7.99 m (6H, Ar-H), 8.09 s (1H,
IR, H and C NMR, and Mass spectral data.
Antibacterial activity against Escherichia coli, –ve,
Bacillus Subtillis, +ve, and antifungal activity against
Candida albicans were evaluated. All the above
compounds demonstrated more potent antibacterial
and antifungal activity than the standard controls.
1
3
Ar-H), 8.53 s (1H, Ar-H), 11.94 s (1H, OH). C NMR
spectrum, δ, ppm: 20.3, 108.5, 111.4, 115.0, 115.2,
1
1
22.3, 123.3, 129.0, 130.6, 131.9, 132.7, 133.6, 135.8,
+
44.9, 153.8, 160.9, 161.2. MS, m/z: 340.01 [M + H] .
(E)-3,5-Dichloro-N'-[(5-methyl-7-nitrobenzofuran-
2
1
-yl)methylene]benzohydrazide (6k). Yield 88%, mp
59–161°C. IR spectrum, ν, cm : 3358, 1694, 1526.
ACKNOWLEDGMENTS
–
1
1
H NMR spectrum, δ, ppm: 2.47 s (3H, CH ), 7.50 s
3
One of us (JP) is thankful to CSIR, New Delhi, for
the award of research fellowship and also thankful to
the Head, Department of Chemistry, Osmania
University, Hyderabad for providing the laboratory
facilities and also thankful to the CFRD, Osmania
University for providing Analytical data. Another
author (NJPS) is thankful to UGC/DST-purse A37/
PURSE/coord/2011) for providing financial assistance.
(
1H, Ar-H), 7.83 d (2H, J = 7.9 Hz, Ar-H), 7.94–7.96
m (2H, Ar-H), 8.05–8.07 m (1H, Ar-H), 8.56 s (1H,
Ar-H), 12.28 s (1H, NH). C NMR spectrum, δ, ppm:
2
1
1
1
3
0.5, 96.3, 109.4, 123.5, 127.2, 128.5, 130.2, 131.3,
32.5, 132.9, 134.5, 138.2, 140.2, 141.5, 145.9, 153.8,
+
63.2, MS, m/z: 392.16 [M + H] .
(
E)-N'-[(5-Methyl-7-nitrobenzofuran-2-yl)meth-
ylene]-4-(methylsulfonyl)benzohydrazide (6l). Yield
–
1
REFERENCES
8
1
1%, mp 147–149°C. IR spectrum, ν, cm : 3781,
1
695, 1524, 1142 (SO Me), 1524. H NMR spectrum,
2
1
2
. Aslam, S.N., Stevenson, P.C., and Phythian, S.J.,
Tetrahedron, 2006, vol. 62, p. 4214. doi org/10.1016/
j.tet.2006.02.015
. de Campos, M.P., Filho, V.C., and da Silva, R.Z., Biol.
Pharm. Bull., 2005, vol. 28, no. 8, p. 1527. doi
org/10.1248/bpb.28.1527
δ, ppm: 2.47 s (3H, CH ), 3.30 s (3H, SO Me), 7.60 s
3
2
(
1H, Ar-H), 7.99 s (1H, Ar-H), 8.09–8.20 m (3H,
Ar-H), 8.27 s (1H, Ar-H), 8.58 s (1H, Ar-H), 9.94 s
1
3
(
1H, Ar-H), 12.35 s (1H, NH). C NMR spectrum, δ,
ppm: 20.3, 43.2, 109.7, 118.1, 122.7, 125.8, 128.7,
1
1
29.2, 130.4, 131.3, 134.4, 137.6, 143.5, 145.1, 153.3,
54.0, 162.1,180.9. MS, m/z: 402.13 [M + H] .
3. Koca, M., Sevi, S., Kirilmis, C., Kazaz, C., Ozbek, B.,
and Otuk, G., Eur. J. Med. Chem., 2005, vol. 40,
p. 1351. doi org/10.1016/j.ejmech.2005.07.004
+
(
E)-N'-[(5-Methyl-7-nitrobenzofuran-2-yl)meth-
4
5
6
7
. Dawood, K.M., Abdel-Gawad, H., Rageb, E.M.,
Ellithey, M., and Mohamed, H.A., Bioorg. Med. Chem.,
ylene]benzohydrazide (6m). Yield 83%, mp 149–151°C.
IR spectrum, ν, cm : 3618, 1645, 1524. H NMR spec-
trum, δ, ppm: 3.43 s (3H, CH ), 7.56–7.62 m (3H,
Ar-H), 7.63–7.65 m (1H, Ar-H), 7.93–7.97 m (3H, Ar-H),
–1
1
2006, vol. 14, p. 3672. doi org/10.1016/j.bmc.2006.01.033
3
. Rajak, H., Behera, C.K., Pawar, R.S., Singour, P.K., and
Kharya, M.D., Chin. Chem. Lett., 2010, vol. 21, no. 10,
p. 1149. doi org/10.1016/j.cclet.2010.04.012
. Patel, H.J., Sarra, J., Caruso, F., Rossi, M., Doshi, U.,
and Stephani, R.A., Bioorg. Med. Chem. Lett., 2006,
vol. 16, p. 4644. doi org/10.1016/j.bmcl.2006.05.102
. Jadhav, V.B., Kulkarni, M.V., Rasal, V.P., Biradar, S.S.,
and Vinay, M.D., Eur. J .Med. Chem., 2008, vol. 43,
p. 1721. doi org/10.1016/j.ejmech.2007.06.023
8
.07 s (1H, Ar-H), 8.58 s (1H, Ar-H), 12.15 s (1H,
1
3
NH). C NMR spectrum, δ, ppm: 20.3, 109.2, 122.5,
1
1
27.7, 128.6, 129.1, 131.8, 132.1, 132.7, 133.0, 133.7,
+
36.8, 145.0, 153.6, 163.3. MS, m/z: 324.21 [M + H] .
(E)-2-Iodo-N'-[(5-methyl-7-nitrobenzofuran-2-yl)-
methylene]benzohydrazide (6n). Yield 79%, mp
–
1
1
53–154°C. IR spectrum, ν, cm : 3375, 1665, 1523.
1
8. Hayakawa, I., Shioya, R., Agatsuma, T., Furukawa, H.,
and Sugano, Y., Bioorg. Med. Chem. Lett., 2004,
vol. 14, p. 3411. doi org/10.1016/j.bmcl.2004.04.079
H NMR spectrum, δ, ppm: 3.46 s (3H, CH ), 7.23–
3
7
7
.29 m (2H, Ar-H), 7.48–7.56 m (2H, Ar-H), 7.90–
.99 m (2H, Ar-H), 8.08 s (1H, Ar-H), 8.36 s (1H, Ar-
9
. Rida, S.M., El-Hawash, S.A.M., Fahmy, H.T.Y.,
Hazzaa, A.A., and El-Meligy, M.M.M., Arch. Pharm.
Res., 2006, vol. 29, no. 10, p. 826. doi 10.1007/
BF02973901
1
3
H), 12.15 s (1H, NH). C NMR spectrum, δ, ppm:
2
1
1
0.3, 94.0, 109.6, 122.6, 127.6, 128.5, 129.2, 131.6,
31.8, 132.7, 133.7, 136.8, 139.2, 140.9, 145.1, 153.3,
+
65.2. MS, m/z: 450.02 [M + H] .
1
0. Reddy, K.A., Lohray, B.B., Bhushan, V., Bajji, A.C.,
Reddy, K.V., Reddy, P.R., Krishna, T.H., Rao, I.N.,
Jajoo, H.K., Rao, N.V.S., Chakrabarti, R., Kumar, T.D.,
and Rajagopalan, R., J. Med. Chem., 1999, vol. 42,
p. 1927. doi 10.1021/jm980549x
CONCLUSIONS
A new series of substituted benzofuran hydrazone
derivatives 6a–6n were synthesized, characterized by
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 9 2017

2
1
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