Synthesis and evaluation of antimicrobial and antioxidant activity of novel 7-Aryl-6H,7H- benzo[f]chromeno[4,3-b]chromen-6-one by MgO nanoparticle as green catalyst

Article abstract of DOI:10.1002/jhet.3796

Using MgO nanoparticle as a recyclable and efficient catalyst, multicomponent reaction of 2-Naphthol, aldehyde derivatives, 4-hydroxycoumarin has led to the synthesis of novel 7-Aryl-6H,7H- benzo[f]chromeno[4,3-b]chromen-6-one derivatives. This study aime

Full text of DOI:10.1002/jhet.3796

Received: 13 August 2019
DOI: 10.1002/jhet.3796
Revised: 25 September 2019
Accepted: 7 October 2019
A R T I C L E
Synthesis and evaluation of antimicrobial
and antioxidant activity of novel 7-Aryl-6H,7H- benzo[f]
chromeno[4,3-b]chromen-6-one by MgO nanoparticle
as green catalyst
Sara Hosseinzadegan | Nourallah Hazeri
| Malek T. Maghsoodlou
Department of Chemistry, Faculty of
Abstract
Science, University of Sistan &
Baluchestan, Zahedan, The Islamic
Republic of Iran
Using MgO nanoparticle as a recyclable and efficient catalyst, multicomponent
reaction of 2-Naphthol, aldehyde derivatives, 4-hydroxycoumarin has led to the
synthesis of novel 7-Aryl-6H,7H- benzo[f]chromeno[4,3-b]chromen-6-one
derivatives. This study aimed to examine the antimicrobial and antioxidant
effects of the synthetic compound in order to reach some benefits, including
the synthesis of new derivatives with biological properties, shorter time, high
yields, and concordance with green chemistry.
Correspondence
Nourallah Hazeri, Department of
Chemistry, Faculty of Science, University
of Sistan & Baluchestan, P. O. Box
98135-674. Zahedan, The Islamic Republic
of Iran.
Email: nhazeri@chem.usb.ac.ir;
n_hazeri@yahoo.com
Funding information
Research Council of University of Sistan
and Baluchestan
1 | INTRODUCTION
2 | RESULTS AND DISCUSSION
Chromen core is a bioactive compound that is found
in many natural compounds such as flavonoids.[1–4]
Many biological operations have been reported for
the compounds containing this core, some of which
are anti-HIV,[5] neuro-protective,[5,6] antidiabetes,[7]
antioxidant,[8,9] and antimicrobial[10–13] operations.
Considering the significance of chromen in terms of
biological operations, the synthesis of its new deriva-
tives and the development of new methods to synthe-
size heterocycles containing chromen seem to be of
paramount importance. We used magnesium oxide
nanoparticles as a green catalyst for the synthesis of
new 7-Aryl-6H,7H- benzo[f]chromeno[4,3-b]chromen-
6-one derivatives at lower temperatures and shorter
time compared to previous studies and then exam-
ined the biological properties (namely antibacterial,
antifungal, and antioxidant) of the synthesized
derivatives.
The structure of MgO nanoparticles was proven using
and Scanning Electron microscopic images (SEM) tech-
niques and X-ray diffraction (XRD) (Figures 1 and 2,
respectively). In SEM, image nanocrystals were deter-
mined as dense flakes with a size range of 30–50 nm. The
XRD patterns of synthesized MgO were similar with the
standard diffraction data of MgO nanoparticles (JCPDS
file No. 89-7746) and peaks observed at (111), (200),
(220), (311), and (222), diffraction planes reveal the cubic
phase of MgO nanoparticles. Average particle size was
calculated to be 23.7 and 25.7 nm according to the
Scherrer equation.[14–16]
In this study, chromine derivatives were synthesized
using multicomponent synthesis and MgO nanoparticles
as a catalyst. (Scheme 1).
The reactions were optimized for amount of MgO
nanoparticles and temperature. In the first stage of optimi-
zation, using 1 mmol beta-naphthol, 1 mmol benzaldehyde,
J Heterocycl Chem. 2019;1–6.
wileyonlinelibrary.com/journal/jhet
© 2019 Wiley Periodicals, Inc.
1

2
HOSSEINZADEGAN ET AL.
TABLE 1 Optimization of reaction conditions
MgO
Temperature Time
Entry NPs (mol%) (ꢀC)
(min) Yield (%)
1
2
3
4
5
6
7
8
9
10
0
5
50
50
50
50
50
50
25
60
70
80
60
45
35
30
25
25
60
15
15
15
0
58
65
81
87
84
37
92
90
86
10
15
20
25
20
20
20
20
FIGURE 1 SEM image MgO nanoparticles
ones. The results of synthesized compounds are shown in
Table 2.
The catalyst was used five times after separation,
washing, and drying in the synthesis of 4a. The recovery
results show that reusing the catalyst does not greatly
reduce the efficiency (Figure 3).
According to previous reports, catalysts such as
1-Methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium Chlo-
ride (MSI),[17] Zr (HSO4)4,
Alum,[19] and melamine
[18]
trisulfonic acid[20] have been used in the synthesis of
these compounds. The results presented in Table 3 show
that MgO nanoparticle have lower temperature, lower
time, and higher efficiency than previous catalysts in the
synthesis of derivatives.
FIGURE 2 XRD spectrum of MgO nanoparticles
The chemical structures of compounds 4a–j were
identified by elemental analyses, 1H NMR and 13C NMR
1
spectrum. In H NMR spectra of 4b; hydrogens of the
methyl groups (N (Me)2) appeared at δ: 3.16 ppm (6H,
s), δ: 6.31 ppm (1H, s, CH). In 13C NMR spectra, methyl
groups of amine appeared at δ: 46.0, ppm, sp3 carbon in
the ring at δ: 36.4 ppm and carbonyl group at δ:
168.1 ppm.
SCHEME 1 Multicomponent synthesis of chromen
derivatives
The proposed mechanism was presented at the below
in Scheme 2.
1 mmol 4-hydroxycoumarin in different amounts of
nanoparticles (0–25 mol%) at 50ꢀC. The results showed that
the best efficiency was 20 mol%. Then, temperature optimi-
zation was carried out and the reaction was tested at 25, 60,
70, and 80ꢀC, and it was found that the highest efficiency
with lowest time were 60ꢀC with a molecular weight of 20%
catalyst (Table 1).
Ten 7-Aryl-6H,7H-benzo[f]chromeno[4,3-b]chromen-
6-one derivatives were synthesized in optimum condi-
tions, five of which were new derivatives. The presented
method in this study caused the formation of compounds
with higher efficiency and shorter time than the previous
2.1 | Antimicrobial evaluation of the
synthesized compounds
The antimicrobial activity includes antimicrobial and
antifungal activity, of the synthesized compounds was
evaluated against three gram-negative bacteria, two
gram-positive bacteria and one fungi. According to the
results concerning, minimum inhibitory concentration
(MIC), minimum bactericidal concentration (MBC), min-
imum fungicidal concentration (MFC) values in Table 4,

HOSSEINZADEGAN ET AL.
3
TABLE 2 Multicomponent
synthesis of 7-Aryl-6H,7H-benzo[f]
chromeno[4,3-b
MP (ꢀC)
Time
(min)
Yield
(%)
Entry
R
Found
Reported
4a
C6H5
20
92
202–203
199–200
[16]
4b
4c
4
3
N (CH3)2 C6H4
15
25
89
85
195–197
New
NO2 C6H4
NO2 C6H4
OH C6H4
235–2237 237–238
[16]
4d
4
10
25
93
257–259
257–258
[17]
4e
2
2
82
84
86
84
246–247
282–283
190–191
193–194
New
New
New
4f
OH 4 OCH3 C6H3 30
4 g
4 h
2,4 (OCH3)2 C6H3
2,5 (OCH3)2 C6H3
15
15
191–192
[17]
4i
4j
3,4 (OCH3)2 C6H3
10
5
91
93
265–266
213–215
New
4
OCH3 C6H4
211–212
[16]
94
92
90
88
86
84
5
4
3
2
1
Run
SCHEME 2 Proposed mechanism for the synthesis of 7-Aryl-
6H,7H-benzo[f]chromeno[4,3-b]chromen-6-one derivatives by MgO
nanoparticle
FIGURE 3 Reusability of MgO NPs in the synthesis of 4a
TABLE 3 Comparison of different methods in the synthesis
7-(phenyl)-6H,7H-benzo[f]chromeno[4,3-b]chromen-6-one (4a)
Subsequently, the compounds containing the hydroxide
group (4e, 4f) showed the next order of antimicrobial
activity. The results were compared with cefazolin, genta-
micin, terbinafine, and tolnaftate as commercial drugs.
In the antibacterial activity, the results indicated that
cefazole has not effect on Acinetobacter baumannii and
Bacillus cereus but the synthesized derivatives, especially
4d, showed good effect. In the antifungal activity, also
tolnaftate had no effect on Aspergillus fumigatus but the
compound 4d showed good effects.
Time
(min)
Temperature
(ꢀC)
Entry
4a
Cat
Yield (%)
90[16]
91[17]
86[18]
89[19]
92
MSI
120
20
80
110
120
120
60
4a
Zr (HSO4)4
Alum
4a
45
4a
MTSA
MgO Nps
60
4a
20
the order of antimicrobial activity was described as
4d>4c>4e>4f>4i>4g>4h>4j>4b>4a. The highest anti-
microbial activity was related to 4d and 4c. The highest
antimicrobial activity of these compounds can be attrib-
uted to the presence of nitro group in their structure.
2.2 | Antioxidant evaluation
In the study of antioxidant activity, the concentration dia-
gram on percent inhibition was plotted and IC50

4
HOSSEINZADEGAN ET AL.
TABLE 4 Antimicrobial activity of 7-aryl-6H,7H-benzo[f]chromeno[4,3-b]chromen-6-one derivatives
Gram-negative bacteria
Gram-positive bacteria
Fungi
5009
1399
1855
1290
1665
1447
Product/
antibiotics
MIC
1024
1024
256
128
256
512
256
256
128
512
8
MBC
2048
2048
512
256
512
1024
512
1024
256
1024
16
MIC
-
MBC
-
MIC
MBC
MIC
MBC
MIC
1024
1024
512
512
512
1024
512
1024
512
1024
8
MBC
2048
2048
1024
1024
1024
2048
1024
2048
512
MIC
-
MIFC
-
4a
4b
4c
4d
4e
4f
-
-
-
-
-
-
512
512
256
1024
1024
-
1024
-
-
-
-
512
512
512
512
512
512
512
512
-
1024
1024
1024
1024
1024
1024
1024
1024
-
1024
256
512
128
128
256
256
512
1024
512
2048
32
256
256
256
512
1024
2048
1024
4096
64
512
64
128
2048
256
512
2048
512
1024
4 g
4 h
4i
-
-
-
-
-
-
1
-
-
-
-
-
4
-
-
-
-
4j
-
-
2048
16
a
0.25
4
0.5
8
b
4
8
32
64
2
4
-
-
TABLE 5 Antioxidant activity of 7-Aryl-6H,7H-benzo[f]
chromeno[4,3-b]chromen-6-one derivatives
(%) Scavenging
concentrations (μg/ml)
Compounds
5
10
39
65
35
25
31
39
53
54
48
48
69
15
49
69
41
32
38
47
64
66
60
59
78
20
57
81
51
36
41
56
75
75
67
65
89
IC50 (μg/ml)
16.05
7.31
4a
4b
4c
4d
4e
4f
24
39
20
11
15
23
35
35
31
30
19.19
27.13
23.53
16.59
9.92
SCHEME 3 Proposed mechanism for radical stability
of DPPH
4 g
4 h
4i
9.66
11.87
12.28
3.33
4j
3 | CONCLUSIONS
Ascorbic acid 52
Using
2-Naphthol,
aldehyde
derivatives,
and
4-hydroxycoumarin, 10 7-Alkyl-6H,7H-benzo[f]chromeno
[4,3-b]chromen-6-one derivatives were synthesized in this
study, five of which were new compounds. MgO
nanoparticles were used as a green and recyclable catalyst
and a new method was suggested for the synthesis of the
7-Alkyl-6H,7H-benzo[f]chromeno[4,3-b]chromen-6-one
derivatives. MgO nanoparticles showed good recyclabil-
ity and can be used up to five times without dramati-
cally reducing efficiency. Biological tests were carried
out on the synthesized compounds, and the compounds rev-
ealed acceptable antimicrobial, antifungal, and antioxidant
calculated from the slope of the line. All the derivatives
4a-j exhibited antioxidant properties with IC50 ranging
from 7.31 to 27.13 μg/mL and IC50 value for ascorbic acid
was obtained as 3.33 μg/mL (Table 5). The order of the
antioxidant properties of the derivatives based on were
4b>4h>4g>4i>4j>4a>4f>4C>4e>4d. Depending on the
structure of the derivatives, the order of the property is
dependent on the radical stability formed. According to
the results, the following mechanism was proposed for
DPPH radical stability (Scheme 3).

HOSSEINZADEGAN ET AL.
5
properties. The novelty of this study is the synthesis of new
derivatives with antimicrobial and antioxidant proper-
ties and the development of a new method and green
catalyst for the synthesis of 7-Alkyl-6H,7H-benzo[f]
chromeno[4,3-b]chromen-6-one derivatives at a shorter
reaction time with higher yields, compared to the pre-
vious methods.
7-(4-(dimethylamino)phenyl)-6H,7H-benzo[f]
chromeno[4,3-b]chromen-6-one (4b)
M.p. 195–197ꢀC; IR (KBr, cm−1): 3046 and 2919 (CH3), 2793
(C H), 1674 (C O); 1H NMR (400 MHz, DMSO-d6) δ: 3.16
(6H, s, 2Me), 6.31 (1H, s, CH), 7.23–7.31 (8H, m, H Ar), 7.45
(1H, d, J = 8.4 Hz, H Ar), 7.51–7.56 (3H, m, H Ar), 7.83
(2H, d, J = 6.3 Hz, H Ar); 13C NMR (75 MHz, DMSO-d6) δ:
36.4, 46.0, 103.5, 116.1, 120.1, 123.5, 124.6, 128.7, 131.6, 153.0,
164.9, 168.1. Anal. Calcd for C28H21NO3: C, 80.17; H, 5.05; N,
11.44. Found: C, 80.15; H, 5.06; N, 11.47.
3.1 | Experimental section
All reagents and solvents obtained from Merck and
Sigma-Aldrich. Antibiotics were acquired from Sigma-
Aldrich. The 1H and 13C-NMR spectra were determined
by a Bruker FT-NMR Ultra Shield-250 spectrometer
(250 and 75 MHz, resp). Elemental analyses were
accomplished for on a Thermo Finnigan Flash EA
microanalyzer. The FT-IR spectrum was recorded on a
Bruker Tensor 27 FT-IR spectrometer using KBr bul-
lets. Melting points of material were determined by a
Kruss type KSP1N melting point meter. Monitoring
progress of the reactions and the purity of the products
were done by TLC (Silica gel, Aluminum Sheets,
Merck). The concentrations of bacterial, fungal suspen-
sions, and absorption of derivatives in antioxidant
activity were determined by using Jenway 6405 UV–V
spectrophotometer. The XRD analysis was carried out
by Bruker D8 X-ray diffractometer with Cu-Kα radia-
tion (λ = 1.5418 Å) in the range of 10–70ꢀ and the scan-
ning rate of 1.5ꢀ/min.
7-(2-hydroxyphenyl)-6H,7H-benzo[f]chromeno[4,3-b]
chromen-6-one (4e)
M.p. 246–247ꢀC; IR (KBr, cm−1): 3256 (O H), 3052 (C H),
1711 (C O); 1H NMR (400 MHz, DMSO-d6) δ: 5.76 (1H, s,
CH), 7.13–7.24 (1H, m, H Ar), 7.33–7.35 (8H, m, H Ar),
7.47 (1H, t, H Ar), 7.51–7.73 (1H, m, H Ar), 8.11 (1H, d,
J = 6.6 Hz, H Ar), 12.25 (1H, s, OH); 13C NMR (75 MHz,
DMSO-d6) δ: 29.1, 114.3, 116.6, 116.7, 117.0, 122.7, 123.1,
124.4, 125.0, 125.8, 128.8, 129.1, 132.7, 133.0, 149.7, 152.5,
152.7, 156.8, 160.9, 161.1. Anal. Calcd for C26H16O4: C,
79.58; H, 4.11. Found: C, 79.59; H, 4.14.
7-(2-hydroxy-4-methoxyphenyl)-6H,7H-benzo[f]
chromeno[4,3-b]chromen-6-one (4f)
M.p. 282–283ꢀC; IR (KBr, cm−1): 3271 (O H), 3074 and
2993 (CH3), 2972 (C H), 1721 (C O); 1H NMR
(400 MHz, DMSO-d6) δ: 3.95 (3H, s, OMe), 5.73 (1H, s,
CH), 6.77 (1H, d, J = 7.2 Hz, H Ar), 7.01–7.12 (2H, m,
H Ar), 7.32–7.73 (8H, m, H Ar), 8.01 (1H, d, J = 7.8 Hz,
H Ar), 12.25 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6)
δ: 29.1, 56.5, 101.0, 111.6, 114.4, 116.6, 116.7, 117.0, 120.1,
122.8, 123.4, 124.4, 125.1, 125.6, 132.7, 132.9, 139.1, 147.8,
152.4, 152.6, 154.4, 160.9. Anal. Calcd for C27H18O5: C,
76.77; H, 4.29. Found: C, 76.78; H, 4.32.
3.2 | Preparation of MgO nanoparticles
The MgO nanoparticles were prepared according to pre-
viously reported.[21]
7-(2,4-dimethoxyphenyl)-6H,7H-benzo[f]chromeno
[4,3-b]chromen-6-one (4 g)
3.2.1 | Synthesis of 7-aryl-6H,7H-benzo[f]
chromeno[4,3-b]chromen-6-one (4a-j)
M.p. 190–191ꢀC; 3012, 2974 and 2939, (CH3), 2723 (C-H),
1
1669 (C=O); H NMR (400 MHz, DMSO-d6) δ: 3.59 (3H, s,
OMe), 3.74 (3H, s, OMe), 6.19 (1H, s, CH), 6.43–6.51 (3H, m,
H Ar), 7.05 (1H, d, J = 8.4 Hz, H Ar), 7.32–7.40 (5H, m,
H Ar), 7.60 (3H, t, H Ar), 7.93 (1H, d, J = 7.8 Hz, H Ar);
13C NMR (75 MHz, DMSO-d6) δ: 32.9, 55.5, 56.1, 99.1, 104.5,
105.6, 116.5, 117.7, 120.3, 124.0, 124.3, 129.0, 132.3, 152.4,
158.7, 159.7, 163.6, 164.4. Anal. Calcd for C28H20O5: C,
77.05; H, 4.62. Found: C, 77.03; H, 4.60.
A mixture of 1 mmol 2-Naphthol (0.144 g), 1 mmol alde-
hyde derivatives, 1 mmol 4-hydroxycoumarin (0.162 g)
and 0.25 mmol MgO nanoparticles (0.02 g) in 2 ml of
ethanol were stirred at 50ꢀC. The reactions were moni-
tored by TLC (n-hexane/ethyl acetate). After completion
of the reaction, 5 ml of acetone was added to the precipi-
tates and MgO nanocatalyst was filtered off. Remove the
filter solution under vacuum conditions. The precipitate
was recrystallized with ethanol. The isolated MgO
nanoparticles washed several times with ethanol and
water, then were dried under vacuum over Al2O3 at
room temperature.
7-(3,4-dimethoxyphenyl)-6H,7H-benzo[f]chromeno
[4,3-b]chromen-6-one (4i)
M.p. 265–266ꢀC; 3021, 3012, 2981 and 2930, (CH3), 2752
1
(C H), 1689 (C O); H NMR (400 MHz, DMSO-d6) δ:
3.59 (3H, s, OMe), 3.73 (3H, s, OMe), 6.32 (1H, s, CH),

6
HOSSEINZADEGAN ET AL.
6.71 (2H, d, J = 8.1 Hz, H Ar), 6.84 (1H, d, J = 8.1 Hz,
H Ar) 7.33–7.41 (5H, m, H Ar), 7.60–7.64 (3H, m,
H Ar), 7.94 (1H, d, J = 7.5 Hz, H Ar), 9.15 (1H, s,
H Ar); 13C NMR (75 MHz, DMSO-d6) δ: 36.1, 55.9, 56.1,
104.9, 111.8, 112.1, 116.5, 118.2, 119.3, 124.3, 132.4, 147.6,
149.0, 152.6, 165.2, 165.4. Anal. Calcd for C28H20O5: C,
77.05; H, 4.62. Found: C, 77.06; H, 4.59.
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Antioxidant activity of derivatives on DPPH was evalu-
ated according to the method of Beyzaei et al.[24] In 4 ml
of the 0.004% (w/v) DPPH methanolic solution, 1 ml of
various concentrations (25, 50, 75, and 100 μg/mL) of all
derivatives in methanol was added and stand for 30 min
at room temperature in darkness. The absorbance was
read against blank at 517 nm. The percent inhibition
(I %) of free radical production from DPPH was calcu-
lated by the equation (1):
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ðA control−A sampleÞ
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%of scavenging =
× 100
ðAcontrolÞ
A control: absorbance of DPPH solution;A sample: absor-
bance of the test compound;All tests were carried out in
triplicate and their average was reported.
How to cite this article: Hosseinzadegan S,
Hazeri N, Maghsoodlou MT. Synthesis and
evaluation of antimicrobial and antioxidant activity
of novel 7-Aryl-6H,7H- benzo[f]chromeno[4,3-b]
chromen-6-one by MgO nanoparticle as green
catalyst. J Heterocycl Chem. 2019;1–6. https://doi.
org/10.1002/jhet.3796
ACKNOWLEDGMENTS
We gratefully appreciate financial support from the Research
Council of University of Sistan and Baluchestan.
ORCID
Nourallah Hazeri https://orcid.org/0000-0002-0560-
7245