Synthesis and antibacterial evaluation of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety

Article abstract of DOI:10.1515/chempap-2016-0090

A series of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety were synthesised and their antibacterial activities against tobacco and tomato bacterial wilts evaluated in vitro. Out of the synthesised compounds, 5g, 5j, 5n, 5m and 5p exhi

Full text of DOI:10.1515/chempap-2016-0090

Chemical Papers 70 (11) 1521–1528 (2016)
DOI: 10.1515/chempap-2016-0090
ORIGINAL PAPER
Synthesis and antibacterial evaluation of novel Schiff base
derivatives containing 4(3 )-quinazolinone moiety
a,b
‡
a
‡
b
b
Mei-Hang Chen *, Xiao-Bing Wang , Bang-Cheng Tang, Xun Zhang
aState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide
and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China
bDepartment of Material and Chemistry Engineering, Tongren University, Guizhou Tongren, Bijiang District 554300, China
Received 2 December 2015; Revised 31 March 2016; Accepted 16 April 2016
A series of novel Schiff base derivatives containing 4(3H)-quinazolinone moiety were synthesised
and their antibacterial activities against tobacco and tomato bacterial wilts evaluated in vitro.
Out of the synthesised compounds, 5g, 5j, 5n, 5m and 5p exhibited excellent antibacterial ac-
tivities against tobacco bacterial wilt, with half maximal effective concentrations (EC50): 160.34,
−
1
1
58.03, 125.94, 148.09 and 133.67 (all in µg mL ), respectively, which were better than the EC50
−
1
of thiodiazole–copper (216.70 µg mL ). Compounds 5j, 5n and 5o also showed good antibacterial
activities against tomato bacterial wilt, with EC50 of 95.20, 90.03 and 83.21 (all in µg mL ) respec-
tively, which were better than the EC50of thiodiazole–copper (99.80 µg mL ). These compounds
−
1
−
1
may prove to be useful as potential antibacterial agents.
ꢀ
c 2016 Institute of Chemistry, Slovak Academy of Sciences
Keywords: Schiff base derivatives, 4(3H)-quinazolinone, synthesis, antibacterial activity
Introduction
such as anti-inflammatory (Giria et al., 2010), an-
tibacterial (Panneerselvam et al., 2009), antifun-
gal (Patel et al., 2012), antimalarial (Zhu et al.,
2010), antiviral (Kumar et al., 2010), and anti-
cancer (Alafeefy et al., 2015). Recent studies of
4(3H)-quinazolinone derivatives have mainly focused
on antibacterial and antifungal activities. For ex-
ample, (E)-3-[2-(substituted-arylideneamino)ethyl]-2-
(arylamino)-4(3H)-quinazolinone derivatives were
synthesised and found to exhibit significant antibac-
terial activities against tobacco and tomato bacterial
wilts (Wang et al., 2013). Novel 4(3H)-quinazolinone
Schiff base derivatives were synthesised and exhibited
potential antifungal activity against Corynespora cas-
siicola Wei and Phomopsis mangiferae Ahmad (Zeng
et al., 2015). Meanwhile, Schiff bases have gained im-
portance in medicinal and pharmaceutical fields due
to showing extensive biological activities, such as an-
tibacterial (Gwaram et al., 2012), antifungal (Bharti
Ralstonia solanacearum, a soil-borne plant bacte-
rial pathogen, was classified as one of the most de-
structive plant pathogens due to the high incidence of
plant mortality; it caused bacterial wilt in a wide range
of potential host plants, including tobacco, tomato,
pepper, aubergine and potato (Li et al., 2011). Nowa-
days, some of traditional bactericides, such as strep-
tomycin, thiodiazole–copper and kocide, are used to
control R. solanacearum in agricultural production.
However, these bactericides cannot effectively control
the bacterial pathogen and may induce resistance in
the host (Wu et al., 2012). Accordingly, the need ex-
ists for the development of novel and more practical
antibacterial reagents.
4
(3H)-Quinazolinones, an important class of nitro-
gen-containing fused heterocycles, are found to ex-
hibit a wide range of pharmacological properties,
*
Corresponding author, e-mail: chenmeihang0123@126.com
‡
The first and the second authors contributed equally to this work
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M. H. Chen et al./Chemical Papers 70 (11) 1521–1528 (2016)
Table 1. Physical properties and analytical data for compounds (4, 5a−5p)
wi (calc.)/%
wi (found)/%
◦
Appearance Reaction time/h Yield/% M.p/ C
Compound
Formula
Mr
C
H
N
4
C15H13N3O2
C22H17N3O2
267.28 brown solid
355.13 grey solid
3
5
80
78
178−179
–
–
–
5
a
184–187
74.35
4.82
4.94
5.18
5.23
4.97
4.85
4.97
5.06
5.10
5.03
4.32
4.22
4.32
4.39
4.14
4.11
4.14
4.17
3.71
4.01
3.71
3.85
3.71
3.66
3.71
3.61
4.03
3.98
4.03
3.92
4.03
4.14
11.82
11.88
11.37
11.67
10.90
10.92
10.90
10.95
10.11
10.03
11.25
11.15
11.25
11.28
10.78
10.69
10.78
10.90
10.30
10.59
9.68
7
4.22
74.78
4.65
71.67
1.74
71.67
1.60
69.39
9.52
70.77
0.83
70.77
0.72
67.78
7.90
67.78
7.73
64.79
4.67
60.84
0.62
60.84
0.86
60.84
0.88
66.00
6.17
66.00
6.21
66.00
5.93
5
b
C23H19N3O2
C23H19N3O3
C23H19N3O3
C24H21N3O4
C22H16FN3O2
C22H16FN3O2
C22H16ClN3O2
C22H16ClN3O2
369.15 grey solid
385.14 grey solid
385.14 grey solid
415.15 grey solid
373.12 grey solid
373.12 grey solid
390.13 grey solid
390.13 grey solid
8
8.5
9
82
81
72
66
71
80
69
74
70
66
60
70
78
65
62
189–191
194–196
192–194
203–205
195–197
199–201
198–200
197–199
201–203
207–209
204–206
201–204
217–219
213–215
210–214
7
5
c
7
5
d
7
5
e
10
3
6
5
f
7
5
5
g
2
7
h
4
6
5
i
j
3
6
5
C22H15FClN3O2 408.14 grey solid
1.5
4
6
5
k
C22H16BrN3O2
C22H16BrN3O2
C22H16BrN3O2
C22H16N4O4
C22H16N4O4
C22H16N4O4
433.04 grey solid
433.04 grey solid
433.04 grey solid
400.12 grey solid
400.12 grey solid
400.12 grey solid
6
9.76
9.68
9.59
9.68
5
l
3
6
5
m
3.5
2
6
9.55
5
n
o
p
13.99
13.87
13.99
13.89
13.99
13.86
6
5
2
6
5
1
6
et al., 2010; Tansir et al., 2008), antimicrobial (Ceyhan
et al., 2011; Bagihalli et al., 2008), anti-HIV (Pandeya
et al., 1999), antiviral (Zhang et al., 2009), anticancer
TOR 22 (Germany) spectrometer using a KBr disk
1
13
technique. H NMR and C NMR (solvent CDCl3 or
DMSO) spectral analyses were performed on a JEOL-
ECX 500 NMR spectrometer (Japan) at ambient tem-
perature using TMS as an internal standard. Chemical
shift is given in δ relative to TMS. Elemental anal-
ysis was performed on an Elementar Vario-III CHN
analyser (Elementar, German). The melting points of
the products were determined on an XT-4 binocu-
lar microscope (Beijing Tech Instrument, China). Un-
less stated otherwise, all reagents were of analytical
grade or chemically pure and purchased from Heowns
Biochem Technologies (China) and Aladdin Chemical
(China). All solvents were dried and distilled prior to
use.
(Mandal et al., 2011), and antioxidant (Li et al.,
2
014) activities. In addition, some Schiff base deriva-
tives of 4(3H)-quinazolinone derivatives were found to
show good antibacterial activities against tobacco and
tomato bacterial wilts (Zeng et al., 2015; Wang et al.,
2
014).
Based on the above findings, an attempt was made
to introduce a Schiff bases fragment into 4(3H)-
quinazolinone derivatives by a condensation addition
reaction to build a novel family of bioactive com-
pounds. Accordingly, a series of novel Schiff bases
derivatives containing 4(3H)-quinazolinone moiety
were synthesised (Fig. 1) and their antibacterial activ-
ities against tobacco and tomato bacterial wilts eval-
uated in vitro.
General procedure for preparation of 3-
(chloromethyl)quinazolin-4(3H)-one (3)
Experimental
3-(Chloromethyl)quinazolin-4(3H)-one (3) was
prepared following the procedures described in the lit-
erature (Ma et al., 2014).
The IR spectra were recorded on a Bruker VEC-
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M. H. Chen et al./Chemical Papers 70 (11) 1521–1528 (2016)
Table 2. Spectral data of compounds (4, 5a−5p)
1523
Compound
Spectral data
1
4
H NMR (500 MHz, DMSO-d6), δ: 8.54 (1H, s, Qu-2-H), 8.21 (1H, d, J = 7.45 Hz, Qu-5-H), 7.86−7.85 (1H, m,
Qu-7-H), 7.51−7.48 (2H, m, Qu-6,8-H), 6.96 (2H, d, J = 8.60 Hz, ArH), 6.74 (2H, d, J = 8.60 Hz, ArH), 5.96 (2H,
s, OCH2), 5.50 (2H, s, NH2);
1
3C NMR (125 MHz, DMSO-d6), δ: 160.28, 148.21, 147.34, 146.31, 137.43, 131.40, 129.05, 128.18, 126.33, 123.05,
1
21.70, 115.21, 72.96
5
a
IR (KBr), ν˜ /cm 1: 1683, 1616, 1507, 1232, 1026
−
1
H NMR (500 MHz, CDCl3), δ: 8.60 (1H, s, –N=CH–), 8.51 (1H, s, Qu-2-H), 8.17 (1H, d, J = 7.45 Hz, Qu-5-H),
7
.88−7.83 (3H, m, Qu-7-H, ArH), 7.68 (1H, d, J = 8.00 Hz, ArH), 7.51−7.48 (4H, m, Qu-6,8-H, ArH), 7.28 (2H, d,
J = 8.60 Hz, ArH), 7.12 (2H, d, J = 8.60 Hz, ArH), 5.96 (2H, s, OCH2)
1
3C NMR (125 MHz, CDCl3), δ: 160.41, 159.97, 155.02, 148.19, 147.95, 146.23, 136.66, 136.63, 131.80, 129.33,
1
29.05, 128.18, 127.98, 126.96, 123.05, 121.90, 117.25, 73.52
−
1
5
b
IR (KBr), ν˜ /cm : 1683, 1616, 1506, 1231, 1067
1
H NMR (500 MHz, CDCl3), δ: 8.58 (1H, s, –N=CH–), 8.55 (1H, s, Qu-2-H), 8.21 (1H, d, J = 7.45 Hz, Qu-5-H),
7
.90−7.80 (3H, m, Qu-7-H, ArH), 7.72−7.60 (2H, m, Qu-6,8-H), 7.28 (2H, d, J = 8.55 Hz, ArH), 7.15 (2H, d, J =
9
.15 Hz, ArH ), 7.08 (2H, d, J = 9.15 Hz, ArH ), 6.00 (2H, s, OCH2), 2.50 (3H, s, CH3)
13
C NMR (125 MHz, CDCl3), δ: 160.69, 159.69, 154.13, 147.87, 147.37, 146.90, 145.37, 141.89, 135.14, 133.70,
29.60, 128.79, 127.85, 127.81, 127.23, 122.47, 116.95, 72.76, 21.73
1
−
1
5
c
IR (KBr), ν˜ /cm : 1680, 1614, 1506, 1243, 1021
1
H NMR (500 MHz, CDCl3), δ: 8.61 (1H, s, –N=CH–), 8.54 (1H, s, Qu-2-H), 8.21 (1H, d, J = 7.45 Hz, Qu-5-H),
7
.88−7.85 (3H, m, Qu-7-H, ArH), 7.72−7.60 (2H, m, Qu-6,8-H), 7.27 (2H, d, J = 8.55 Hz, ArH), 7.15 (2H, d, J =
9
.15 Hz, ArH), 7.07 (2H, d, J = 9.15 Hz, ArH), 5.99 (2H, s, OCH2), 3.83 (3H, s, OCH3)
13
C NMR (125 MHz, CDCl3), δ: 160.40, 159.26, 154.65, 154.86, 148.20, 146.65, 135.61, 135.42, 130.81, 128.16,
27.98, 127.79, 126.96, 122.86, 121.90, 117.27, 114.76, 73.55, 55.92
1
−
1
5
d
IR (KBr), ν˜ /cm : 1682, 1621, 1505, 1232, 1023
1
H NMR (500 MHz, CDCl3), δ: 8.81 (1H, s, –N=CH–), 8.51 (1H, s, Qu-2-H), 8.18 (1H, d, J = 8.00 Hz, Qu-5-H),
8.11 (1H, d, J = 5.75 Hz, ArH), 7.85 (1H, t, J = 6.65 Hz, ArH), 7.85 (1H, t, J = 7.75 Hz, Qu-7-H ), 7.69 (1H, d,
J = 8.00 Hz, ArH), 7.57−7.47 (3H, m, Qu-6,8-H, ArH), 7.22 (2H, d, J = 9.15 Hz, ArH). 7.13 (2H, t, J = 8.60 Hz,
ArH), 5.96 (2H, s, OCH2), 3.85 (3H, s, OCH3)
1
3C NMR (125 MHz, CDCl3), δ: 160.40, 159.66, 154.91, 154.86, 148.20, 146.99, 135.60, 133.50, 128.16, 127.79,
1
27.20, 126.96, 124.46, 122.88, 121.91, 121.17, 117.33, 112.50, 73.58, 56.28
−
1
5
e
IR (KBr), ν˜ /cm : 1684, 1615, 1507, 1233, 1024
1
H NMR (500 MHz, CDCl3), δ: 8.34 (1H, s, –N=CH–), 8.33 (1H, s, Qu-2-H), 8.20 (1H, s, Qu-5-H), 7.80−7.71 (2H,
m, Qu-7,8-H), 7.58 (1H, s, ArH), 7.55 (1H, t, J =7.45 Hz, J = 8.05 Hz, Qu-6-H), 7.28 (1H, s, ArH), 7.19 (1H, d,
J = 8.55 Hz,ArH), 7.09 (1H, d, J = 9.02 Hz, ArH), 6.93 (1H, d, J = 8.05 Hz,ArH), 5.99 (2H, s, OCH2), 3.97−3.94
(
6H, 2s, 2× OCH3)
1
3C NMR (125 MHz, CDCl3), δ: 160.59, 159.19, 153.90, 151.92, 149.41, 147.75, 147.31, 145.26, 134.87, 129.49,
1
27.73, 127.12, 124.36, 122.32, 121.82, 116.90, 110.41, 108.69, 72.71, 55.99
−
1
5
f
IR (KBr), ν˜ /cm : 1682, 1614, 1507, 1225, 1024
1
H NMR (500 MHz, CDCl3), δ: 8.74 (1H, s, –N=CH–), 8.51 (1H, s, Qu-2-H), 8.17 (1H, d, J = 8.00 Hz, Qu-5-H),
8
.06 (1H, t, J = 6.65 Hz, ArH), 7.85 (1H, t, J = 7.50 Hz, Qu-7-H), 7.68 (1H, d, J = 8.00 Hz, ArH), 7.58−7.52 (2H,
m, Qu-6,8-H), 7.32−7.28 (4H, m, ArH), 7.13 (2H, d, J = 8.60 Hz, ArH), 5.97 (2H, s, OCH2)
1
3
C NMR (125 MHz, CDCl3), δ: 160.42, 159.75, 155.35, 155.24, 148.11, 147.65, 145.73, 135.69, 135.22, 133.25,
30.51, 128.76, 128.18, 127.18, 126.96, 122.25, 121.89, 116.82, 72.91
1
−
1
5
g
IR (KBr), ν˜ /cm : 1683, 1615, 1506, 1234, 1021
1
H NMR (500 MHz, CDCl3), δ: 8.39 (1H, s, –N=CH–), 8.34 (1H, d, J = 8.00 Hz, Qu-5-H), 8.21 (1H, s, Qu-2-H),
7
8
5
.88 (1H, d, J = 5.75 Hz, ArH), 7.86 (1H, d, J = 5.75 Hz, ArH), 7.79−7.77 (2H, m, Qu-7,8-H), 7.55 (1H, t, J =
.05 Hz, Qu-6-H), 7.19 (1H, d, J = 8.60 Hz, ArH), 7.16 (1H, d, J = 8.60 Hz, ArH), 7.10 (1H, d, J = 9.15 Hz, ArH),
.99 (2H, s, OCH2)
13
C NMR (125 MHz, CDCl3), δ: 160.58, 159.91, 157.99, 154.23, 147.75, 146.81, 145.24, 134.88, 132.50, 130.68,
30.61, 127.73, 127.12, 122.36, 121.81, 116.87, 116.00, 72.62
1
−
1
5
h
IR (KBr), ν˜ /cm : 1684, 1614, 1506, 1230, 1022
1
H NMR (500 MHz, CDCl3), δ: 8.39 (1H, s, –N=CH–), 8.34 (1H, d, J = 8.05 Hz, Qu-5-H), 8.21 (1H, s, Qu-2-H),
7
.81−7.78 (3H, m, ArH, Qu-7-H), 7.73 (1H, d, J = 8.05 Hz, Qu-8-H), 7.55 (1H, t, J = 6.85 Hz, Qu-6-H), 7.44 (1H,
d, J = 8.60 Hz, ArH), 7.21 (1H, d, J = 9.15 Hz, ArH), 7.10 (1H, d, J = 8.55 Hz, ArH), 6.00 (2H, s, OCH2)
1
3
C NMR (125 MHz, CDCl3), δ: 160.60, 159.83, 157.98, 154.38, 147.73, 146.61, 145.25, 137.25, 134.91, 134.65,
29.84, 129.07, 128.31, 127.74, 127.14, 122.44, 121.81, 116.88, 72.61
1
−
1
5
i
IR (KBr), ν˜ /cm : 1681, 1616, 1508, 1229, 1026
1
H NMR (500 MHz, CDCl3), δ: 8.83 (1H, s, –N=CH–), 8.52 (1H, s, Qu-2-H), 8.17 (1H, d, J = 6.90 Hz, Qu-5-H),
8.11 (1H, d, J = 7.45 Hz, ArH), 7.86 (1H, t, J = 6.55 Hz, ArH), 7.85 (1H, t, J = 15.45 Hz, Qu-7-H), 7.68 (1H, d,
J = 8.00 Hz, ArH), 7.57−7.50 (3H, m, Qu-6,8-H, ArH), 7.45 (1H, t, J = 8.15 Hz, ArH), 7.31 (2H, d, J = 8.60 Hz,
ArH), 7.14 (2H, d, J = 8.60 Hz, ArH), 5.97 (2H, s, OCH2)
1
3C NMR (125 MHz, CDCl3), δ: 160.41, 159.26, 155.52, 155.47, 148.19, 147.94, 145.91, 135.63, 135.41, 133.25,
130.59, 128.76, 128.18, 127.98, 126.96, 123.26, 121.89, 117.30, 73.51
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M. H. Chen et al./Chemical Papers 70 (11) 1521–1528 (2016)
Table 2. (continued)
Compound
Spectral data
IR (KBr), ν˜ /cm 1: 1682, 1616, 1509, 1231, 1024
−
5
j
1
H NMR (500 MHz, CDCl3), δ: 8.73 (1H, s, –N=CH–), 8.56 (1H, s, Qu-2-H ), 8.21 (1H, d, J = 6.90 Hz, Qu-5-H),
7
.90−7.59 (3H, m, Qu-6,7,8-H), 7.56 (1H, t, J = 8.15 Hz, ArH), 7.47 (1H, d, J = 8.00 Hz, ArH), 7.47 (1H, d, J =
5
.65 Hz, ArH),7.33 (2H, d, J = 8.60 Hz, ArH), 7.19 (2H, d, J = 8.60 Hz, ArH), 6.01 (2H, s, OCH2)
13
C NMR (125 MHz, CDCl3), δ: 160.77, 159.76, 155.01, 152.66, 148.43, 147.55, 147.30, 145.50, 134.98, 134.77,
27.52, 127.34, 127.14, 126.31, 126.11, 122.40, 121.25, 116.68, 115.69, 72.88
1
−
1
5
k
IR (KBr), ν˜ /cm :1683, 1616, 1507, 1234, 1021
1
H NMR (500 MHz, CDCl3), δ: 8.64 (1H, s, –N=CH–), 8.55 (1H, s, Qu-2-H), 8.21 (1H, d, J = 6.30 Hz, Qu-5-H),
7
.90−7.85 (3H, m, Qu-7-H, ArH), 7.73−7.71 (3H, m, Qu-8-H, ArH), 7.62 (1H, t, J = 8.05 Hz, Qu-6-H), 7.34 (1H,
d, J = 9.15 Hz, ArH), 7.17 (1H, d, J = 9.15 Hz, ArH), 6.00 (2H, s, OCH2)
1
3
C NMR (125 MHz, CDCl3), δ: 159.76, 158.12, 154.58, 147.55, 147.30, 145.19, 135.22, 134.97, 131.75, 130.18,
27.52, 127.33, 126.31, 124.62, 122.51, 121.26, 116.59, 72.86
1
−
1
5
l
IR (KBr), ν˜ /cm : 1681, 1615, 1508, 1230, 1025
1
H NMR (500 MHz, CDCl3), δ: 8.65 (1H, s, –N=CH–), 8.56 (1H, s, Qu-2-H), 8.21 (1H, d, J = 6.30 Hz, Qu-5-H),
8
.09 (1H, s, ArH), 7.99 (1H, t, J = 5.75 Hz, Qu-7-H), 7.92−7.87 (2H, m, Qu-6,8-H), 7.72 (1H, d, J = 8.00 Hz, ArH),
7
.62 (1H, t, J = 8.05 Hz, ArH), 7.35 (2H, d, J = 9.20 Hz, ArH), 7.18 (2H, d, J = 9.15 Hz, ArH), 6.01(2H, s, OCH2)
13
C NMR (125 MHz, CDCl3), δ: 159.78, 157.72, 154.67, 147.57, 147.27, 144.98, 138.34, 134.98, 133.61, 130.94,
30.56, 127.50, 127.35, 122.62, 122.01, 119.34, 116.63, 72.87
1
−
1
5
m
IR (KBr), ν˜ /cm : 1684, 1616, 1507, 1234, 1020
1
H NMR (500 MHz, CDCl3), δ: 8.79 (1H, s, –N=CH–), 8.56 (1H, s, Qu-2-H ), 8.21 (1H, d, J = 6.30 Hz, Qu-5-H),
8
.13 (1H, d, J = 6.30 Hz, ArH), 7.90 (1H, t, J = 7.45 Hz, Qu-7-H), 7.76−7.71 (2H, m, Qu-8-H, ArH), 7.62 (1H, t,
J = 7.45 Hz, J = 6.90 Hz, Qu-6-H), 7.52−7.46 (2H, m, ArH), 7.34 (2H, d, J = 9.15 Hz, ArH), 7.19 (2H, d, J =
.15 Hz, ArH), 6.01( 2H, s, OCH2)
9
1
3
C NMR (125 MHz, CDCl3, ppm) δ: 159.76, 157.21, 154.89, 147.55, 147.30, 145.22, 134.97, 133.93, 133.17, 132.88,
28.54, 128.05, 127.52, 127.34, 126.31, 125.11, 122.55, 121.26, 116.70, 72.88
1
−
1
5
n
IR (KBr), ν˜ /cm : 1684, 1616, 1506, 1232, 1025
1
H NMR (500 MHz, CDCl3), δ: 8.34 (1H, d, J = 6.30 Hz, –N=CH–), 8.25 (1H, d, J =8.05 Hz, Qu-2-H), 8.20 (1H,
s, Qu-5-H), 7.80−7.71 (2H, m, Qu-7,8-H), 7.55−7.52 (3H, m, Qu-6-H, ArH), 7.40−7.34 (3H, m, N=CHPh, ArH),
7
.18−7.05 (6H, m, ArH), 5.99 (2H, s, OCH2)
13
C NMR (125 MHz, CDCl3), δ: 159.76, 155.19, 155.05, 149.11, 147.30, 144.84, 134.98, 133.59, 131.57, 130.02,
29.28, 127.53, 127.34, 126.32, 124.40, 122.72, 121.26, 116.67, 72.87
1
−
1
5
o
IR (KBr), ν˜ /cm : 1683, 1616, 1506, 1231, 1021
1
H NMR (500 MHz, CDCl3), δ: 8.71 (1H, s, –N=CH–), 8.52 (1H, s, Qu-2-H), 8.35 (1H, d, J = 6.30 Hz, ArH), 8.32
(1H, d, J = 8.00 Hz, ArH), 8.22 (1H, d, J = 8.05 Hz, Qu-5-H), 7.79 (1H, t, J = 5.75 Hz, Qu-7-H), 7.73 (1H, d, J =
8.00 Hz, Qu-8-H), 7.66 (1H, t, J = 8.00 Hz, ArH), 7.56 (1H, t, J = 7.45 Hz, Qu-6-H), 7.26 (2H, d, J = 8.60 Hz,
ArH), 7.18 (2H, d, J = 8.60 Hz, ArH), 6.02 (2H, s, OCH2)
1
3C NMR (125 MHz, CDCl3), δ: 159.76, 158.33, 154.27, 147.25, 147.37, 145.34, 135.34, 134.97, 132.11, 130.18,
1
27.62, 127.33, 126.37, 124.82, 122.54, 121.21, 116.78, 72.82
−
1
5
p
IR (KBr), ν˜ /cm : 1683, 1615, 1506, 1230, 1027
1
H NMR (500 MHz, CDCl3), δ: 8.66 (1H, s, –N=CH–), 8.57 (1H, s, Qu-2-H ), 8.37 (2H, d, J = 8.60 Hz, ArH), 8.21
(1H, d, J = 8.05 Hz, Qu-5-H), 8.18 (2H, d, J = 9.20 Hz, Ar), 7.99 (1H, t, J = 8.60 Hz, Qu-7-H), 7.72 (1H, d, J =
8.05 Hz, Qu-8-H), 7.62 (1H, t, J = 6.85 Hz, Qu-6-H), 7.43 (1H, d, J = 9.15 Hz, ArH), 7.20 (1H, d, J = 9.15 Hz,
ArH), 6.02 (2H, s, OCH2)
1
3C NMR (125 MHz, CDCl3), δ: 160.76, 157.21, 155.18, 148.54, 147.53, 147.30, 141.64, 134.99, 134.77, 129.32,
127.34, 127.14, 126.31, 125.92, 123.40, 122.92, 121.43, 116.58, 72.82
General procedure for preparation of 3-((4-
aminophenoxy)methyl)quinazolin-4(3H)-one
General procedure for preparation of title com-
pounds 5a–5p
(
4)
Aromatic aldehyde (1.1 mmol) was added to a
solution of intermediate 4 (1.0 mmol) in anhydrous
ethanol (15 mL). The resulting mixture was refluxed
for 1−10 h. When the reaction was complete, the sol-
vent was removed under vacuum, and the residue was
re-crystallised from EtOH (Wang et al., 2013) to ob-
tain compounds 5a−5p with a yield of 60–82 %. The
properties and analytical data for the title compounds
are listed in Table 1, and the spectral data are shown
in Table 2.
A mixture of compound 2 (0.1 mol), intermediates
(0.1 mol) and K2CO3 (0.12 mmol) was dissolved in
CH3CN (300 mL) and refluxed. After refluxing for 3 h,
the reaction solution was poured into 1 L of water to
produce a solid precipitate; the precipitate was then
recrystallised from ethanol to obtain intermediate 4
Bae et al., 2012). The properties and analytical data
for compound 4 are listed in Table 1, and the spectral
data are shown in Table 2.
3
(
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M. H. Chen et al./Chemical Papers 70 (11) 1521–1528 (2016)
1525
Fig. 1. Synthetic route of title compounds.
Table 3. Optimisation of reaction conditions for intermediate
for 5.0 h
I = (Ctur − Ttur)/Ctur × 100 %
(1)
4
where Ctur is the corrected turbidity value of bacte-
rial growth on untreated NB, Ttur is the corrected tur-
bidity value of bacterial growth on treated NB. Sim-
ilarly, the solvent for tomato bacterial wilt was (SM;
◦
a
Entry Catalyst Solvent
Temperature/ C Yield /%
1
2
3
4
5
6
7
8
9
0
NaHCO3 CH3CN
a.t.
a.t.
a.t.
35
35
35
35
50
65
80
31
57
48
52
61
70
63
80
85
92
K2CO3
NaOH
CH3CN
CH3CN
CH2Cl2
(CH3)2CO
CH3CN
DMF
1
0.0 g of peptone, 5.0 g of glucose, 1.0 g of casein acid
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
hydrolysate, 1 L of distilled water, pH 7.0−7.2), and
thiodiazole–copper served as positive control. Some of
the title compounds were tested against tobacco bac-
terial wilt and tomato bacterial wilt at five double-
declining concentration (200, 100, 50, 25, and 12.5 (all
CH3CN
CH3CN
CH3CN
1
−1
in µg mL )), and EC50 of compounds were calculated
with SPSS 17.0.
a) Yield of crude compound 4.
Results and discussion
Synthesis
Antibacterial biological assay
The synthetic route for novel Schiff bases deriva-
tives containing 4(3H)-quinazolinone moiety is shown
in Fig. 1. The title compounds were synthesised from
2-aminobenzoic acid in five steps including cyclisation,
addition, chlorination, condensation, and etherifica-
tion reaction. To optimise the reaction conditions of
intermediate 4, the influence of catalyst, temperature
and solvent were tested. The results indicate that the
catalyst, solvent and temperature had a pronounced
effect on the yield. Table 3 shows that a maximum
yield of 92 % was achieved when K2CO3 was used
The antibacterial activities of the title compounds
against R. solanacearum were evaluated using the tur-
bidimeter test (Wang et al., 2013; Xu et al., 2012). The
title compounds were dissolved in 150 µL of dimethyl-
formamide (DMF) and diluted with water contain-
ing Tween-20 (0.1 vol. %) to obtain concentrations
−
1
−1
of 200 µg mL and 100 µg mL , with thiodiazole–
copper serving as a positive control. The liquid sample
(1 mL) was added to the non-toxic nutrient broth (NB;
1
.5 g of beef extract, 2.5 g of peptone, 0.5 g of yeast
◦
powder, 5.0 g of glucose and 500 mL of distilled water,
as catalyst, and refluxed (80 C) for 5.0 h in CH3CN
pH 7.0−7.2) liquid medium in 4 mL tubes. Next, NB
(Table 3, entry 10).
(
40 µL) containing tobacco bacterial wilt was added
The structures of the synthesised compounds were
characterised by IR, 1H NMR, C NMR and ele-
mental analyses. The IR spectral data of the title
compounds showed characteristic absorption bands
13
to solvent NB (5 mL) containing the test compounds
or thiodiazole–copper. The inoculated test tubes were
◦
incubated at (30 ± 1) C under continuous shaking
−
1
−1
at 180 min for 48 h. The culture growth was moni-
tored spectrophotometrically by measuring the optical
density at 600 nm (OD600) and expressed as corrected
turbidity. The relative inhibitory rate (I, %) compared
with a blank assay was calculated as follows:
at 1684−1680 cm , which were assigned to C—O
of 4(3H)-quinazolinone. The absorption bands of the
−CH—N− of the skeleton-stretching frequency ap-
−
1
1
peared at 1618−1611 cm . The H NMR spectra of
the title compounds, using CDCl3 as a solvent, showed
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M. H. Chen et al./Chemical Papers 70 (11) 1521–1528 (2016)
Table 4. Antibacterial activity of compounds 5a−5p against tobacco and tomato bacterial wilt
Tobacco bacterial wilt Tomato bacterial wilt
Compound
00/(µg mL 1)
−
100/(µg mL
−1
)
200/(µg mL
−1
)
−1
100/(µg mL )
2
5
a
51.2 ± 1.9
44.4 ± 2.2
48.4 ± 3.4
44.6 ± 2.6
40.1 ± 2.5
79.7 ± 3.2
80.1 ± 3.1
73.5 ± 2.5
74.2 ± 4.0
88.6 ± 2.8
64.0 ± 2.1
63.6 ± 1.9
59.0 ± 2.5
95.2 ± 1.5
89.4 ± 3.2
93.5 ± 1.6
63.1 ± 1.3
30.4 ± 2.4
20.5 ± 2.6
27.3 ± 3.5
29.2 ± 1.8
19.4 ± 2.4
40.3 ± 2.3
28.3 ± 2.1
35.6 ± 3.5
38.0 ± 1.9
49.9 ± 1.8
26.3 ± 3.6
47.8 ± 1.6
43.4 ± 4.2
57.3 ± 1.3
52.6 ± 2.3
52.3 ± 1.6
30.2 ± 2.1
67.5 ± 1.4
47.5 ± 3.6
49.0 ± 4.0
45.8 ± 3.8
46.2 ± 3.2
80.8 ± 3.5
84.9 ± 1.2
60.1 ± 3.2
55.4 ± 3.9
86.8 ± 3.8
51.4 ± 2.5
47.3 ± 1.5
33.2 ± 1.9
87.2 ± 3.5
88.6 ± 4.0
81.9 ± 1.8
86.2 ± 3.6
30.3 ± 2.1
23.6 ± 1.5
28.2 ± 1.0
31.9 ± 2.8
20.3 ± 2.0
46.1 ± 2.6
55.3 ± 2.3
32.4 ± 2.6
34.6 ± 2.7
51.4 ± 1.9
41.7 ± 2.1
23.8 ± 2.4
10.4 ± 1.7
38.1 ± 1.5
48.2 ± 1.4
55.0 ± 2.3
57.3 ± 1.4
5
b
5
c
5
d
5
5
e
f
5
5
g
h
5
5
i
j
5
k
5
l
5
m
5
5
5
n
o
p
thiodiazole–copper
the –OCH2– yielding singlet peak and appeared at
δ 5.96−6.02. A singlet ranging from δ 8.34−8.81 be-
longed to the 4(3H)-quinazolinone ring –N—CH−
terial activities against tomato bacterial wilt (55.3 %,
51.4 %, 56.1 %, 55.2 %, and 53.0 %, respectively)
at 100 µg mL , which compared with thiodiazole–
copper (57.3 %).
Based on the preliminary bioassays, the EC50 val-
ues of the test compounds, as well as thiodiazole-
copper, are listed in Table 5. Notably, compounds
−
1
proton. The chemical shifts at δ 160.69−159.76,
1
3
1
59.97−155.19, and 73.52−72.62 in C NMR con-
firmed the existence of the −C—O, −N—CH− and
CH2− groups, respectively.
−
5
g, 5j, 5n, 5o, and 5p exhibited excellent activities
Antibacterial activity
against tobacco bacterial wilt, with half maximal ef-
fective concentration (EC50) values of 160.34, 158.03,
−
1
The antibacterial activity against tomato bac-
terial wilt and tobacco bacterial wilt of the syn-
thesised Schiff bases derivatives containing 4(3H)-
quinazolinone moiety were evaluated in vitro by the
turbidimeter test. Commercial agricultural antibac-
terial thiodiazole-copper was used as a control. The
results shown in Table 4 indicate that most of the
compounds exhibited significant antibacterial activ-
ity against tomato and tobacco bacterial wilt. Among
the title compounds, 5j, 5n, 5o, and 5p showed ex-
cellent antibacterial activities against tobacco bac-
terial wilt at 200 µg mL , with inhibition activi-
ties of 88.6 %, 95.2 %, 89.4 %, and 93.5 %, respec-
tively, which were better than that achieved by the
commercial bactericide thiodiazole–copper (63.1 %).
Meanwhile, the antibacterial activities of compounds
125.94, 148.09 and 133.67 (all in µg mL ), respec-
tively, which were better than that of thiodiazole–
−
1
copper (216.70 µg mL ). Meanwhile, compounds 5j,
5n, and 5o, showed good activities against tomato
bacterial wilt in vitro, with EC50 values of 95.20,
90.03, and 83.21 (all in µg mL ), respectively,
which were better than that of thiodiazole–copper
−
1
−
1
(99.80 µg mL L).
SAR analyses
−
1
The preliminary structure-activity relationship
(SAR) indicated that the antibacterial activities of
the title compounds exhibited potential against to-
bacco and tomato bacterial wilt for the different aryl
groups introduced into the title compounds. The data
for the antibacterial activities indicated that the re-
lationships of the antibacterial activities with differ-
ent R were deduced on the basis of the antiviral ac-
tivities in Tables 4 and 5. When R was substituted
with electron-withdrawing aryl (4-FPh, 2-F-6-ClPh,
2-NO2Ph, 3-NO2Ph, and 4-NO2Ph), the correspond-
ing title compounds showed excellent antibacterial ac-
tivities. For example, the antibacterial activities of
compounds 5j, 5n, 5o, and 5p against tobacco and
tomato bacterial wilt achieved more than 80.0 % at
5
j, 5l, 5m, 5n, 5o, and 5p against tomato bacterial
−
1
wilt at 100 µg mL
were 49.9 %, 47.8 %, 43.4 %,
5
7.3 %, 52.6 % and 52.3 %, respectively, which ex-
ceeded that of thiodiazole–copper (30.2 %). In addi-
tion, compounds 5j, 5n and 5o demonstrated sat-
isfactory antibacterial activities against tomato bac-
terial wilt, with inhibition rates of 86.8 %, 87.2 %
and 88.6 %, respectively, which were close to that of
−
1
thiodiazole-copper (86.2 %) at 200 µg mL . Com-
pounds 5g, 5j, 5n, 5o, and 5p showed good antibac-
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M. H. Chen et al./Chemical Papers 70 (11) 1521–1528 (2016)
1527
Table 5. EC50 values of compounds against tobacco and
Acknowledgements. This work was financially supported by
the opening foundation of the key laboratory of green pesti-
cide and agricultural bioengineering, Ministry of Education,
Guizhou University (no. 2010GDGP0105), Science and Tech-
nology Foundation of Guizhou Province (no. [2011]2080), and
Natural Science Foundation of Guizhou Province Education
tomato bacterial wilt
Tobacco bacterial Tomato bacterial
wilt
wilt
Compound
EC50/(µg mL 1) EC50/(µg mL
−
−1
)
(no. 2010079).
5
f
173.23 ± 2.1
160.34 ± 1.8
190.10 ± 2.0
187.42 ± 1.2
158.03 ± 1.7
125.94 ± 3.0
148.09 ± 2.6
133.67 ± 2.1
216.70 ± 1.1
117.24 ± 2.6
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145.26 ± 2.0
137.59 ± 2.2
95.20 ± 2.9
90.03 ± 1.5
83.21 ± 1.8
102.36 ± 2.2
99.80 ± 2.3
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