Boosting 3H-Benzo[f]chromen-3-one Chalcone with Anti-inflammatory Drugs: Synthesis, Characterization, and Evaluation of Cytotoxicity and Antimicrobial Activity

Article abstract of DOI:10.1134/S1070428020090195

Abstract: A series of novel 3H-benzo[f]chromen-3-one derivatives bearing non-steroidal anti-inflammatory drug moieties were synthesized with good yields. Benzo[f]coumarin chalcone was prepared via Claisen–Schmidt condensation between 2-acetyl-3H-benzo[f]c

Full text of DOI:10.1134/S1070428020090195

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 9, pp. 1622–1627. © Pleiades Publishing, Ltd., 2020.
Boosting 3H-Benzo[f]chromen-3-one Chalcone
with Anti-inflammatory Drugs: Synthesis, Characterization,
and Evaluation of Cytotoxicity and Antimicrobial Activity
a,
b
a
Q. A. H. Jaber *, N. A. Abdul-Rida , and Sh. Adnan
a
Department of Chemistry, College of Education, University of Al-Qadisiyah,
Diwaniyah, 58001 Iraq
b
Department of Chemistry, College of Science, University of Qadisiyah,
Diwaniyah, 58001 Iraq
*
e-mail: qassimjaber99@gmail.com
Received March 18, 2020; revised March 26, 2020; accepted March 29, 2020
Abstract—A series of novel 3H-benzo[f]chromen-3-one derivatives bearing non-steroidal anti-inflammatory
drug moieties were synthesized with good yields. Benzo[f]coumarin chalcone was prepared via Claisen–
Schmidt condensation between 2-acetyl-3H-benzo[f]chromen-3-one and 4-hydroxybenzaldehyde in basic
medium and was then esterified with carboxylic acids (drugs) in the presence of phosphoryl chloride and
1
anhydrous zinc(II) chloride. The newly synthesized compounds were characterized by FT-IR and H and
1
3
C NMR spectra and elemental analyses and were screened in vitro for their anticancer and antimicrobial
activity. Some of the tested compounds showed a good activity in comparison to standard drugs.
Keywords: benzo[f]chromen-3-one, chalcone, anti-inflammatory drugs, esterification
DOI: 10.1134/S1070428020090195
INTRODUCTION
RESULTS AND DISCUSSION
Fused chromenes play a very significant role in
medicinal chemistry and are used as valuable basic
core for the design and synthesis of pharmacologically
active compounds [1, 2]. Coumarin and its derivatives
possess a wide range of biological activities such as
antimicrobial [3], anticancer [4–7], anticoagulant [8],
analgesic [9], ulcerogenic [10], antiviral [11], anti-
malarial [12], anti-inflammatory [13, 14], antidepres-
sant [15], and antioxidant [16, 17] and inhibit HIV
protease [18], acetylcholinesterase [19], monoamine
oxidase B (MAO-B) [20], and steroid 5α-reductase
Initially, we prepared 3-acetyl-5,6-benzocoumarin 3
by treatment of 2-hydroxynaphthaldehyde 1 with ethyl
acetoacetate 2 in the presence of piperidine. The con-
densation of 3 with 4-hyroxybenzaldehyde gave benzo-
coumarin chalcone 4, and the latter was coupled with
anti-inflammatory drugs, namely clonixin, sulindac,
mefenamic acid, flurbiprofen, indomethacin, keto-
profen, and oxaprozin) via esterification in the presence
of phosphoryl chloride and anhydrous zinc chloride
(Scheme 1).
The structures of 5–11 were determined by spec-
1
13
troscopic methods (FT-IR, H and C NMR) and
[21]. In addition, compounds with a chalcone backbone
elemental analyses. The FT-IR spectra of 5–11 showed
are known to possess a wide range of biological
activities [22, 23]. Many coumarin derivatives were
designed and found to be promising as organic
fluorescent materials for potential applications in
biochemical and biological imaging due to their light
emission properties [24]. In this work, we report the
synthesis of a new series of benzocoumarin derivatives
conjugated with anti-inflammatory drugs and their
biological evaluation.
−1
characteristic absorption bands at 1756–1730 cm
attributed to lactone carbonyl stretching and at 1730–
−1
1
715 cm due to ester carbonyl stretching, whereas
−
1
the band at 1690–1650 cm was assigned to chalcone
carbonyl stretching. Other absorption bands due to
substituents present in their molecules were also
observed (see Experimental).
1
In the H NMR spectra of 5–11, protons of the
benzocoumarin moiety gave almost similar patterns.
1
622

BOOSTING 3H-BENZO[f]CHROMEN-3-ONE CHALCONE
1623
Scheme 1.
CHO
O
O
O
O
Piperidine
EtOH
OH
+
Me
–
Me
OEt
O
1
2
3
CHO
9
8
7
10
O
O
O
HO
piperidine
RCOOH
POCl /ZnCl
1
10a
3
2
2
6
a
1
0b
O
3
6
4
a
O
OH
F
O
O
O
R
5
4
5–11
O
5
'
Me
5
"
Me
S
Me
2"
H
Me
4'
7'
H
3'
6'
Cl
N
2'
6"
Me
N
2'
R =
4'
5'
6'
5'
2"
3
"
6
"
N
4"
6" 3'
2'
4
"
2
"
5
"
6'
5"
4'
6"
F
Me
6, sulindac
5
, clonixic acid
MeO
7, mefenamic acid
8, flurbiprofen
4
'
6'
Ph 4'
Me
N
N
2'
2
'
Ph 5'
O
O
Me
O
Cl
9
, indomethacin
10, ketoprofen
11, oxaprozin
The 1-H proton resonated as a singlet at δ 8.60–
.20 ppm, and signals in the region δ 8.24–7.84 ppm
were assigned to protons of the benzene ring fused to
the coumarin fragment. The enone fragment of 5–11
gave two doublets at δ 7.20 and 8.04 ppm, indicating
trans configuration of the chalcone C=C double bond.
pounds 5, 6, 9, and 10 at a concentration of 80 μM
showed the most potent inhibition of cancer cell
proliferation (Fig. 1), whereas the other compounds
displayed very weak or no activity in comparison with
docetaxel. The calculated IC50 values are presented in
Table 1.
8
In the 13C NMR spectra of 5–11, the chalcone
Some of the synthesized compounds displayed
promising activity against both bacterial and fungal
strains (Table 2). Compounds 5, 8, 9, and 11 showed
carbonyl carbon atom resonated at δ 175.0–168.0 ppm,
C
and the ester and lactone carbonyl carbon signals were
located at δ 168.0–161.0 and 162.0–159.0 ppm,
C
Table 1. Cytotoxicity of compounds 5–11
IC , ꢀM
respectively. The signals at δ 155.0–150.0 and 152.0–
C
1
0a
1
1
46.0 ppm were assigned to C and C of the benzo-
5
0
Compound no.
coumarin fragment, respectively. The double-bonded
carbon atoms of the enone linkage resonated in the
SK-LU-1
21.6±0.72
30.2±2.42
>100
MCF-7
24.7±0.88
41.5±2.05
>100
5
6
7
8
9
regions δ 128.0–124.5 and 145.0–138.0 ppm. The
C
other signals were also consistent with the proposed
structures (see Experimental).
>100
>100
Compounds 5–11 were screened in vitro for their
antitumor activities against SK-LU-1 and MCF-7
cancer cell lines by the standard MTT assay using
docetaxel as a positive control. The cell viability tests
were carried out at different concentrations. Com-
25.3±0.85
21.5±1.69
>100
36.9±1.07
39.2±1.83
>100
1
0
11
Docetaxel
25±1.35
30±1.42
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020

1624
JABER et al.
Table 2. Antimicrobial activity of compounds 5-11
Inhibition zone diameter, mm
Compound
E. coli
no.
S. aureus
C. albicans
A. niger
5
0 ꢀg/mL 100 ꢀg/mL 50 ꢀg/mL 100 ꢀg/mL 50 ꢀg/mL 100 ꢀg/mL 50 ꢀg/mL 100 ꢀg/mL
5
6
7
8
9
0
11
3
18
5
9
8
16
17
8
8
9
15
12
13
4
2
4
4
8
2
4
4
10
2
3
5
11
12
2
20
18
5
3
7
5
10
12
8
5
11
20
13
23
16
9
12
10
11
20
22
4
1
11
6
6
6
11
8
19
20
15
2
5
7
Cephalexin
Fluconazole
DMSO
12
8
14
9
11
13
13
15
21
25
0
0
0
0
a good activity against E. coli at a concentration of
00 ꢀg/mL. Compounds 5, 6, and 10 were also active
matory drugs through an ester linkage were success-
fully synthesized and were screened for cytotoxicity
and antimicrobial activity. The compounds containing
OMe, Cl, F, and NH substituents showed good anti-
cancer, antibacterial, and antifungal activities, and they
can be regarded as potential anticancer and anti-
microbial agents. Further tests are required to prove
their in vivo activity.
1
against S. aureus at the same concentration. Further-
more, compounds 5, 6, 7, and 9 exhibited a good
inhibitory activity against C. albicans. However, none
of the compounds tested (except for 7) were active
against A. niger (Table 2).
In conclusion, a series of new 5,6-benzocoumarin
chalcone derivatives conjugated with anti-inflam-
EXPERIMENTAL
SK-LU-1
(a)
The melting points were measured on a Stuart
SMP30 melting point apparatus (Switzerland) and are
uncorrected. The IR spectra were recorded in KBr on
a Shimadzu FT-IR 8201 PC spectrophotometer. The
NMR spectra were obtained on a Varian Inova spec-
5
6
7
8
9
10
11
4
3
2
1
0
0
0
0
0
1
13
trometer at 500 MHz for H and 125.65 MHz for
C
with tetramethylsilane as internal standard. Analytical
silica gel 60 F254 TLC plates were purchased from
Merck. Elemental analyses (C, H, N) were carried out
by using a Vario 3000 elemental analyzer (Shimadzu,
Japan). All reagents were obtained from commercial
suppliers and were used without further purification.
1
0
20
40
60
80
Concentration, μg/mL
MCF-7
(b)
5
4
3
2
1
0
0
0
0
0
0
3
-Acetyl-3H-benzo[f]chromen-3-one. Ethyl aceto-
5
6
7
8
9
acetate 2 (1.327 mg, 10.2 mmol) was added with
stirring to a solution of 2-hydroxynaphthaldehyde 1
(1.722 mg, 10 mmol) in anhydrous ethanol (15 mL)
containing a few drops of piperidine, and the mixture
was stirred until a solid precipitated. The solid product
was filtered off, washed with water, dried, and recrys-
tallized from ethanol. Yield 93%, yellow crystals,
mp 186–188°C, R 0.59. IR spectrum, ν, cm : 3031,
931 (C–H), 1735, 1681 (C=O), 1612, 1558, 1450
(C=C), 1211 (C–O). H NMR spectrum (DMSO-d ), δ,
1
0
1
0
20
40
60
80
Concentration, μg/mL
−
1
f
Fig. 1. Cytotoxicity of benzo[f]coumarin derivatives 5–11
against (a) SK-LU-1 and (b) MCF-7 cancer cell lines after
exposure for 48 h.
2
1
6
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020

BOOSTING 3H-BENZO[f]CHROMEN-3-ONE CHALCONE
1625
ppm: 8.10 s (1H, 1-H), 7.89 d (1H, 5-H), 7.84 d (1H,
4-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
yl)prop-1-en-1-yl]phenyl 2-methyl-1-[(Z)-4-(meth-
anesulfinyl)benzylidene]-1H-indene-3-carboxylate
(6). Yield 68%, brown crystals, mp 212–214°C,
8
-H), 7.68–7.04 m (4H, Harom), 2.21 s (3H, Me).
1
3
C NMR spectrum (DMSO-d ), δ , ppm: 172.0
6
C
3
10a
1
(
2-C=O), 161.7 (C O), 155.5 (C ), 137.6 (C ), 135.1–
13.4, 29.5 (Me). Found, %: C 75.35; H 4.12.
C H O . Calculated, %: C 75.62; H 4.23.
−
1
1
R 0.63 (hexane–EtOAc, 7:3). IR spectrum, ν, cm :
f
3055, 2931 (C–H), 1735, 1728, 1660 (C=O), 1626,
15
10
3
1
1
566, 1542 (C=C), 1157, 1141, 1080 (C-O). H NMR
(
E)-2-[3-(4-Hydroxyphenyl)prop-2-enoyl]-3H-
spectrum (DMSO-d ), δ, ppm: 8.42 s (1H, 1-H), 8.19 d
6
benzo[f]chromen-3-one (4). A solution of compound 3
(1H, 6′-H), 8.06 d (1H, 5-H), 8.03 d (1H, 8-H), 7.86 d
(
(
1.191 mg, 5 mmol) and 4-hydroxybenzaldehyde
0.61 mg, 5 mmol) in ethanol was stirred at 50°C for
(
1H, 13-H), 7.75–6.93 m (9H, Harom.), 2.76 s (3H,
1
3
SMe), 2.40 s (3H, Me). C NMR spectrum
6
h in the presence of piperidine (TLC). After cooling,
11
15
(DMSO-d ), δ , ppm: 167.8 (C ), 161.6 (C ), 161.4
6 C
the mixture was stirred for 1 h at room temperature and
left overnight, and the solid product was filtered off,
washed with water, dried, and recrystallized from
ethanol. Yield 73%, brown crystals, mp 203–205°C,
3
10a
4a
1
2′
(C ), 151.1 (C ), 149.1 (C ), 147.5 (C ), 142.5 (C ),
4
b
13
15
1
41.9 (C ), 141.0 (C ), 136.4 (C ), 133.0–117.4
(Carom), 41.1 (SMe), 13.2 (Me). Found, %: C 75.85;
−
1
H 4.31. C H O S. Calculated, %: C 75.91; H 4.35.
4
1
28
6
R 0.59. IR spectrum, ν, cm : 3471 (O–H), 3078, 3031,
f
2
985 (C–H), 1738, 1675 (C=O), 1604, 1558, 1458
4-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
yl)prop-1-en-1-yl]phenyl 2-(2,3-dimethylanilino)-
benzoate (7). Yield 74%, white crystals, mp 197–
1
(
(
C=C), 1218, 1049 (C–O). H NMR spectrum
DMSO-d ), δ, ppm: 9.80 s (1H, OH), 8.42 s (1H, 1-H),
6
8
.07 d (1H, 5-H), 8.04 d (1H, 8-H), 7.86 d (1H,
199°C, R 0.56 (hexane–EtOAc, 8:2). IR spectrum, ν,
cm : 3288 (NH), 3062, 2977, 2931 (C–H), 1732,
f
1
3
−1
C H CH=), 7.68–6.76 m (8H, Harom). C NMR spec-
6
4
trum (DMSO-d ), δ , ppm: 171.1 (=CHC=O), 159.5
1715, 1665 (C=O), 1604, 1589 (C=C), 1527 (δNH),
6
C
3
4a
10a
1
1
(
C =O), 157.8 (C ), 149.1 (C ), 137.6 (C ), 135.1–
1205, 1056 (C–O). H NMR spectrum (DMSO-d ), δ,
6
1
19.2 (Carom). Found, %: C 77.56; H 4.29. C H O .
ppm: 9.37 br.s (1H, NH), 8.48 s (1H, 1-H), 8.21 d (1H,
3b-H), 8.10 d (1H, 5-H), 8.09 d (1H, 8-H), 7.93 d (1H,
22
14
4
Calculated, %: C 77.18; H 4.12.
1
2
3-H), 7.91–7.05 m (14H, Harom.), 2.31 s (3H, Me),
Compounds 5–11 (general procedure). A mixture
of the corresponding carboxylic acid (1 mmol), chal-
cone 4 (1 mmol), zinc chloride (1 mmol), and phos-
phoryl chloride (10 mL) was stirred at 65–70°C for 5–
1
3
.21 s (3H, Me). C NMR spectrum (DMSO-d ), δ ,
6
C
11
15
3
10a
ppm: 171.0 (C ), 164.1 (C ), 159.5 (C ), 155.5 (C ),
4
a
2b
1
1
49.2 (C ), 145.8 (C ), 145.0 (C ), 137.6–114.5
Carom), 22.1 (Me), 18.5 (Me). Found, %: C 78.92;
H 5.01; N 2.63. C H NO . Calculated, %: C 78.57;
(
8
h. After completion of the reaction (TLC), the
3
7
27
5
mixture was allowed to cool down to 25°C and poured
onto crushed ice with stirring. The precipitate was
collected by filtration, washed with cold water, dried,
and recrystallized from an appropriate solvent.
H 4.81; N 2.48.
4-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
yl)prop-1-en-1-yl]phenyl 2-(2-fluoro-[1,1′-bi-
phenyl]-4-yl)propanoate (8). Yield 73%, yellow
4
-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
powder, mp 205–207°C, R 0.55 (hexane–EtOAc, 9:1).
f
yl)prop-1-en-1-yl]phenyl 2-(3-chloro-2-methyl-
anilino)pyridine-3-carboxylate (5). Yield 39 mg
−
1
IR spectrum, ν, cm : 3039, 2908 (C–H), 1738, 1721,
668 (C=O), 1604, 1566 (C=C), 1172, 1085 (C–O),
1
(
(
(
(
65%), yellow powder, mp 236–238°C, R 0.55
hexane–EtOAc, 9:1). IR spectrum, ν, cm : 3313
NH), 3062, 2977, 2931 (C–H), 1752, 1718, 1696
f
1
−
1
987 (C–F). H NMR spectrum (DMSO-d ), δ, ppm:
6
8
7
.24 s (1H, 1-H), 8.13 d (1H, 5-H), 7.94 d (1H, 8-H),
.89 d (1H, 13-H), 7.87–6.89 m (12H, Harom), 3.54 t
C=O), 1643 (C=N), 1612, 1566 (C=C), 1542 (δNH),
1
3
1
(1H, 16-H), 1.93 d (3H, Me). C NMR spectrum
1
211, 1033 (C–O), 645 (C–Cl). H NMR spectrum
11
15
(
DMSO-d ), δ , ppm: 173.6 (C ), 167.5 (C ), 161.4
6 C
(
DMSO-d ), δ, ppm: 10.25 br.s. (1H, NH), 8.35 s (1H,
6
3
3b
10a
4a
(
C ), 160.1 (C ), 153.6 (C ), 155.5, 149.9 (C ),
1
7
-H), 8.23 d (1H, 1H, 6′-H), 8.19 d (2H, 5-H, 8-H),
1
13
1
46.9 (C ), 144.7 (C ), 135.5–117.0 (Carom), 49.9
.94 d (1H, 13-H), 7.92–6.67 m (14H, Harom.), 2.28 s
1
6
13
(C ), 14.6 (Me). Found, %: C 78.52; H 4.69.
C H FO . Calculated, %: C 78.16; H 4.43.
(3H, Me). C NMR spectrum (DMSO-d ), δ , ppm:
6 C
11
15
2′
3
3
7
25
5
1
74.5 (C ), 165.0 (C ), 162.5 (C ), 161.1 (C ), 156.8
6′
10a
4a
1
1
(C ), 155.0 (C ), 152.0 (C ), 150.0 (C ), 146.0 (C ),
4-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
13
3′
2
1
45.0 (C ), 143.9 (C ), 140.3 (C ), 136.1–119.6
yl)prop-1-en-1-yl]phenyl 1-(4-chlorobenzoyl)-5-
(Carom), 18.3 (Me). Found, %: C 71.68; H 3.90; N 4.83.
methoxy-2-methyl-1H-indole-3-carboxylate (9).
C H ClN O . Calculated, %: C 71.61; H 3.95; N 4.77.
Yield 58%, white crystals, mp 229–232°C, R 0.47
35
23
2
5
f
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 9 2020

1626
JABER et al.
−
1
(
2
hexane–EtOAc, 8:2). IR spectrum, ν, cm : 3055,
coumarin derivatives 5–11, were then added at concen-
trations of 10, 20, 40, 60, and 80 μM to 3 wells, and the
plate was further incubated for 48 h. After replacing
the old medium with fresh medium, an MTT solution
(50 μL of 0.5 mg/mL in DMEM) was added to each
well, and the plate was returned to incubator for
another 4 h. The resulting formazan crystals were
dissolved by adding 100 μL of DMSO to each well.
The extent of MTT reduction within cells to formazan
was calculated by measuring the absorbance at
λ 570 nm on an ELISA microplate reader. The obtained
data were used to calculate cell viability percentage
931 (C–H), 1756, 1743, 1692, 1677 (C=O), 1604,
566 (C=C), 1215, 1064, 1041 (C–O), 685 (C–Cl).
H NMR spectrum (DMSO-d ), δ, ppm: 8.61 s (1H,
-H), 8.08 d (1H, 5-H), 8.02 d (1H, 8-H), 7.86 d (1H,
3-H), 7.76–6.67 (15H, Harom), 3.50 s (3H, OMe),
.19 s (3H, Me). C NMR spectrum (DMSO-d ), δ ,
ppm: 175.0 (C ), 164.7 (C ), 160.3 (C ), 159.9 (C ),
55.6 (C ), 151.0 (C ), 147.9 (C ), 144.1 (C ), 142.0
C ), 139.2 (C ), 134.0–116.1 (Carom), 50.1 (OMe),
3.2 (Me). Found, %: C 71.25; H 3.74; N 2.19.
C H ClNO . Calculated, %: C 71.91; H 3.92; N 2.10.
1
1
6
1
1
2
1
3
6
C
11
16
15
3
5′
10a
4a
1
1
(
1
13
2″
40
26
7
(
Fig. 1), and the IC values are given in Table 1.
50
4
-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
yl)prop-1-en-1-yl]phenyl 2-(3-benzoylphenyl)-
Antimicrobial activity assay. Antimicrobial activ-
propanoate (10). Yield 63%, brown powder, mp 220–
ity of the synthesized compounds was investigated
in vitro against both Gram positive bacteria
(Staphylococcus aureus) and Gram negative bacteria
(Escherichia coli), as well as fungi (Candida albicans,
Aspergillus niger) using the broth dilution method [26].
Preparation of nutrient broth, subculture, base layer
medium, and agar medium was made according to the
standard procedure. The standard and test compounds
were dissolved in DMSO to obtain a concentration of
50 or 100 μg/mL. The samples were incubated at 37°C
for 24 h (bacteria) or at 25°C for 7 days (fungi), and
the inhibition zone diameter (mm) was measured
(Table 2). Cephalexin and fluconazole were used as
standard antibiotics to compare the results.
2
22°C, R 0.54 (hexane–EtOAc, 9:1). IR spectrum, ν,
f
−
1
cm : 3047, 2923 (C–H), 1733, 1724, 1704, 1665
1
(C=O), 1612, 1566 (C=C), 1164, 1020 (C–O). H NMR
spectrum (DMSO-d ), δ, ppm: 8.49 s (1H, 1-H), 8.08 d
6
(1H, 5-H), 8.05 d (1H, 8-H), 7.89 d (1H, 13-H), 7.85–
7
.04 m (14H, Harom), 3.35–3.31 q (1H, 15-H), 1.39 d
13
(3H, Me). C NMR spectrum (DMSO-d ), δ , ppm:
6 C
18
11
15
3
1
77.9 (C ), 170.0 (C ), 168.1 (C ), 155.5 (C ), 154.5
10a
4a
1
13
1c
(C ), 150.0 (C ), 148.0 (C ), 144.0 (C ), 140.0 (C ),
3
b
16
1
39.2 (C ), 138.5–115.7 (C
), 37.7 (C ), 13.0
arom
(
Me). Found, %: C 78.32; H 4.15. C H O . Calculat-
38 26 6
ed, %: C 78.88; H 4.53.
4
-[(1E)-3-Oxo-3-(3-oxo-3H-benzo[f]chromen-2-
yl)prop-1-en-1-yl]phenyl 3-(4,5-diphenyl-1,3-oxazol-
-yl)propanoate (11). Yield 49%, brown solid,
mp 210–212°C, R 0.57 (hexane–EtOAc, 8:2). IR spec-
ACKNOWLEDGMENTS
2
f
The authors are thankful to Department of Chemistry,
College of Education, University of Al-Qadisiyah for
providing necessary facilities. We also thank Dr. Najim A.
Al-Masoudi for his sustained guidance to carry out the lab
work.
−
1
trum, ν, cm : 3047, 2939 (C–H), 1740, 1720, 1664
C=O), 1650 (C=N), 1604, 1542, 1488 (C=C), 1203,
(
1
1
180, 1072 (C–O). H NMR spectrum (DMSO-d ), δ,
6
ppm: 8.42 s (1H, 1-H), 8.17 d (1H, 5-H), 8.07 d (1H,
8
2
-H), 7.91 d (1H, 13-H), 7.84–7.04 (9H, H ), 2.90–
arom
1
3
.84 t (2H, 16-H), 2.73–2.69 t (2H, 15-H). C NMR
CONFLICT OF INTEREST
The authors declared the absence of conflict of interest.
REFERENCES
1
1
spectrum (DMSO-d ), δ , ppm: 174.1 (C ), 167.6
6
C
1
5
3
2′
10a
(
(
1
C ), 163.5 (C ), 156.8 (C ), 150.0 (C ), 149.9
C ), 147.5 (C ), 146.7 (C ), 144.9 (C ), 141.7 (C ),
37.6–117.0 (Carom), 30.7 (COCH ), 26.5 (2′-CH ).
4a
1
5′
13
4′
2
2
Found, %: C 77.13; H 4.09. C H NO . Calculat-
4
0
27
6
ed, %: C 77.78; H 4.41.
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