Synthesis, characterization and antimicrobial activities of some novel bis-chalcones

Article abstract of DOI:10.1007/s00044-011-9696-z

A series of novel bis-chalcones 3a-n were synthesized in excellent yields by condensation reaction of 1,4-diacetylbenzene with various aldehydes in ethanol 96% and aqueous NaOH at room temperature. All compounds were characterized by IR, ¹H and

Full text of DOI:10.1007/s00044-011-9696-z

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2012) 21:1811–1816
DOI 10.1007/s00044-011-9696-z
ORIGINAL RESEARCH
Synthesis, characterization and antimicrobial activities of some
novel bis-chalcones
•
Akbar Mobinikhaledi Mehdi Kalhor
•
Hossein Jamalifar
Received: 19 May 2010 / Accepted: 8 June 2011 / Published online: 25 June 2011
Ó Springer Science+Business Media, LLC 2011
Abstract A series of novel bis-chalcones 3a–n were
synthesized in excellent yields by condensation reaction of
1,4-diacetylbenzene with various aldehydes in ethanol 96%
and aqueous NaOH at room temperature. All compounds
diseases, there is still a need for new and effective agents to
help bring these diseases under control. Among the cur-
rently identified antimicrobial agents, chalcones are widely
distributed in nature and considered as the precursors for
flavonoid synthesis in plants. They also with proper sub-
stitution have recently been isolated from Broussonetia
papyrifera, known to selectively inhibit enzymes like
protein tyrosine phosphatase 1B (PTP1B) (Chan et al.,
2002) and aldose reductase (Severi et al., 1998). Chemi-
cally, chalcones consist of an open chain in which the two
aromatic rings are joined by a three-carbon unsaturated
carbonyl system. Chalcones can be easily obtained through
the Claisen–Schmidt condensation of benzaldehyde and
acetophenone using either basic or acidic catalysts (Davey
and Tivey, 1958; Lyle and Paradis, 1955). These com-
pounds are not only a segment of biologically important
but also a versatile intermediate for the synthesis of het-
erocyclic compounds (Nagaraj and Reddy, 2008; Bhat
et al., 2009). Compounds with a chalcone-based structure
have shown an impressive array of pharmacological
activities including anticancer (Ducki et al., 1998; Mod-
zelewska et al., 2006), antiinflammatory (Hsieh et al.,
2000), antimalarial (Li et al., 1995; Bhattacharya et al.,
2009) and anti-protozoal (Li et al., 1995; Liu et al., 2001)
activities. Furthermore, many of chalcones exhibit benefi-
cial biological activities, such as antimicrobial (Nowa-
kowska, 2007), anti-HIV (Artico et al., 1998), antibacterial
(Selvakumar et al., 2007), antitumor (Gschwendt et al.,
1984) and antioxidant (Bhat et al., 2009; Vaya et al., 1997)
activities.
1
were characterized by IR, H and 13C NMR, UV spec-
troscopy and elemental analysis. The antimicrobial activi-
ties of synthesized compounds were also evaluated. The
most of these compounds exhibited a good activity against
Staphylococcus aureus, Escherichia coli and Candida
albicans microorganisms. Some of them showed signifi-
cant activities.
Keywords Bis-chalcones ꢀ Microorganisms ꢀ
Antimicrobial activities
Introduction
Despite recent advances in our understanding of the bio-
logical processes leading to the development of microbial
A. Mobinikhaledi (&) ꢀ M. Kalhor ꢀ H. Jamalifar
Department of Chemistry, Arak University, Arak 38156-879,
Iran
e-mail: akbar_mobini@yahoo.com
A. Mobinikhaledi ꢀ M. Kalhor ꢀ H. Jamalifar
Department of Chemistry, Payame Noor University,
Tehran 19395-4697, Islamic Republic of Iran
In view of these observations and also due to our
interests in synthesis of biologically active heterocycles
(Tehranchian et al., 2005; Mobinikhaledi et al., 2010), we
report synthesis of some novel biological active bis-
chalcones.
A. Mobinikhaledi ꢀ M. Kalhor ꢀ H. Jamalifar
Department of Drug and Food Control Faculty of Pharmacy,
Tehran University of Medical Sciences, Tehran, Iran
123

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Med Chem Res (2012) 21:1811–1816
Results and discussion
377–306 nm, 280–234 nm and 261–220 nm assigned to
n ? pH, p ? pH and n ? rH transitions, respectively.
The band at 377–306 nm was assigned to the transition
involving the carbonyl portions (C=O) of chalcone group.
The two other absorption bands were due to transitions of
Synthesis
The general synthetic strategy employed to prepare the bis-
chalcone derivatives is based on the Claisen–Schmidt
condensation (Davey and Tivey, 1958; Lyle and Paradis,
1955). Firstly, the reaction between benzaldehyde and
1,4-diacetylbenzene in the presence of NaOH as a base
using various solvents including water, which known as an
attractive medium for many organic reactions, was con-
sidered at room temperature. The results indicated that the
reaction is accomplishable in water with the yield of 65%
and the highest yield obtained for EtOH with 94% in 18 min
time. The results for compound 3a are comparable with
those reported by pervious method (Hasegawa et al., 1985).
Then a series of the bis-chalcones 3a–n were prepared
by condensing aromatic aldehydes and 1,4-diacetylbenzene
to form the expected compounds using aqueous sodium
hydroxide as a catalyst in ethanol at room temperature
(Scheme 1). The products were isolated after addition of
aqueous sodium hydroxide to the well stirred mixture of
aldehyde and 1,4-diacetylbenzene as the unsaturated bisk-
etones, which yielded the trans-alkene as a major isomer
(E-form, J = 15.3–15.8 Hz) as judged by 1H NMR
spectroscopy.
1
aryl rings. In H NMR spectra of compounds 3a–n, the
aromatic protons resonate as a multiple at 6.86–8.31 ppm
depending on the substituent on the Ar group. The appear-
ance of singlet signals at the region between 8.07–8.36 ppm
is attributed to the resonance of the 1,4-phenylene ring
protons. The presence of doublet signals at the regions
between 7.18–7.85 and 7.75–8.18 ppm are due to the reso-
nance of the double bond protons of the adjacent carbonyl
group. The 13C NMR spectra of compounds 3a–n showed
signals between 111.1–161.9 ppm due to the resonance of
aryl and unsaturated carbons. The appearance of signals at
the region between 189.3–190.8 ppm attributed to the car-
bon resonance of the C=O group is in support of the expected
structures.
Antimicrobial activity
The results of the bioassay are given in Table 1. A cursory
view of the data indicates that most of the compounds exhibit
a moderate to good activity against the Gram negative strain.
Compounds 3f, 3i do not exert a significant effect against the
three microorganisms. It is noteworthy that compounds 3a,
3b, 3d, and especially 3e have moderate to potent bacteri-
cidal effects on three microorganisms.
1
The H NMR data of compounds 3b, 3e, 3h and 3n,
show that these compounds exist either as Z-form or Z/E-
form (J = 9.1–9.3 Hz) (Yoshizawa and Shioiri, 2006).
These compounds are insoluble in water and also have low
solubility in the most common organic solvents.
Although compounds 3k–n have the most antibacterial
effect on the gram negative Escherichia coli, they do not
show any antifungal activity. Perhaps, presence of the nitro
and methoxy groups on the 4-position of the phenyl ring is
the reason why these two compounds show the most fun-
gicidal activity. The same way, probably, compound 3e has
the potential to be a good antimicrobial candidate should it
acquire methoxy, nitro or chloro groups on 4-position of
the phenyl group that the research is ongoing in this regard.
In addition, investigation of the minimum inhibitory con-
centration (MIC) values of the potent derivatives against
The structure of synthesized compounds was established
by means of their IR, UV, 1H NMR, 13C NMR spectra and
elemental analyses. The assignment of selected character-
istic IR bands provides significant indications for the for-
mation of the bis-chalcones 3a–n. The appearance of a
strong absorption band between 1655 and 1666 cm-1 region
is due to stretching vibration of the carbonyl group at adja-
cent unsaturated bond. The UV spectra of the bis-chalcone
analogues in methanol, exhibited three absorption bands at
Scheme 1 Synthesis route of
compounds 3a–n
O
CHO
O
i
R
2
R
R
+
O
3a-n
O
1
2
R
3a H
3h 2-OMe
3i 3-OMe
3j 4-OMe
3k 3,4-OMe
3l 3-Br
3b 2-Cl
3c 3-Cl
3d 4-Cl
i: NaOH/ EtOH/RT
3e 2-NO2
3f 3-NO2
3g 4-NO2
3m 4-Br
3n 2-OH
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Med Chem Res (2012) 21:1811–1816
1813
From a chemical perspective, these compounds have
low solubility in common solvents such as water, EtOH
and MeOH. So it is possible that if their solubility is
improved, these compounds would demonstrate a more
potent anti-microbial effect. Research on this aspect is
ongoing.
Table 1 Antimicrobial activities of bis-chalcones 3a–n (zone of
inhibition in mm)
No.
Compound
S. aureus
E. coli
C. albicans
1
3a
10
13
17
2
3b
10
27
12
3
3c
NA
10
13
12
4
3d
23
12
5
3e
15
21
15
Experimental
6
3f
NA
10
NA
13
NA
25
7
3g
All the used chemicals were purchased from Merck or
Fluka Company. Melting points were determined using an
electro thermal digital apparatus and are uncorrected.
Elemental analyses were performed on a Vario EL III
elemental analyzer. IR spectra were performed on a Galaxy
series FTIR 5000 spectrometer using KBr discs. NMR
spectra were recorded on a Bruker (300 MHz) spectrom-
eter. Chemical shifts (ppm) were referenced in the internal
standard tetramethylsilane (TMS). UV spectra were
recorded on a Diod Array UV–Vis Hp 8450 spectrometer.
The reactions were monitored by thin layer chromatogra-
phy (TLC).
8
3h
NA
NA
NA
11
NA
NA
NA
30
9
9
3i
NA
22
10
11
12
13
14
15
16
3j
3k
NA
NA
NA
NA
NT
21
3l
10
30
3m
9
30
3n
13
30
Gentamicin
Amphotricin B
23
24
NT
NT
Dimethyl sulfoxide (DMSO) only, control for compounds and
references
NA Not active, NT not tested
General procedure for the synthesis of bis-chalcones
three microorganisms indicates that compounds 3g and
3l–n have the highest bactericidal activity (50 lg/ml)
against the E. coli and compound 3e has a high activity
(100 lg/ml) against all three microorganisms (Table 2).
Additionally, compound 3g has the highest antifungal
activity relative to other compounds (50 lg/ml) on
C. albicans fungus.
(3a–n) (Scheme 1)
A solution of diacetylbenzene (0.1 g, 0.6 mmol) and the
corresponding aromatic aldehyde (1.2 mmol) in 15 ml of
ethanol was treated with 2 ml of NaOH (0.048 g,
1.2 mmol) at 5–10°C. The reaction mixture was stirred at
room temperature for desired time. After completion of the
reaction, it was diluted with water (5 ml). The aqueous
solution was acidified with dilute HCl. The obtained solid
was filtered, washed thoroughly with water and dried. The
crude product was purified by recrystallization from
appropriate solvent.
Table 2 Minimum inhibitory concentration (MIC) of the selected
compounds against certain microbial strains (lg/ml)
Compound
C. albicans
E. coli
S. aureus
3a
3b
3c
3d
3e
3g
3h
3j
200
100
NT
200
100
200
NT
NT
200
200
200
100
200
100
300
100
100
50
200
200
300
200
100
50
1,10-(1,4-Phenylene)bis(3-phenylprop-2-en-1-one) (3a)
Yellowish solid, reaction time: 18 min, m.p. 210°C, 94%
yield, recrystallization solvent: benzene/MeOH; IR (KBr):
t 3053 (w), 1655 (s, C=O), 1599 (s), 1448 (m), 1332 (s),
1226 (s), 1035 (m), 983 (m), 837 (m), 754 (s), 682
(m) cm-1; 1H NMR (CDCl3, 300 MHz): dH 7.45–7.47 (m,
6H, H–ph), 7.53 (d, 2H, J = 15.7 Hz, CO–CH), 7.67 (m,
4H, H–ph), 7.84 (d, 2H, J = 15.7 Hz, C=CH), 8.14 (s, 4H,
C6H4) ppm; 13C NMR (CDCl3, 75 MHz): dC 121.8, 128.6,
128.7, 129.0, 130.9, 134.6, 141.3, 145.8, 190.1
(C=O) ppm; Anal. Calcd. for C24H18O2: C, 85.18; H, 5.36;
found: C, 84.92; H, 5.33%; UV/vis kmax (MeOH) 264, 274,
320 nm.
NT
NT
100
50
300
300
NT
NT
NT
NT
3k
3l
3m
3n
50
50
Disc diffusion method used to determine the MICs (Chand et al.,
1994). DMSO only, control for compounds
NT not tested
123

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Med Chem Res (2012) 21:1811–1816
1,10-(1,4-Phenylene)bis(3-(2-chlorophenyl)prop-2-en-1-
one) (3b)
(m, 10H, H–Ar, CO–CH and C=CH), 8.28 ((s, 4H, C6H4),
8.31 (d, 2H, J = 7.6 Hz, H–Ar) ppm; Anal. Calcd. for
C24H16N2O6: C, 67.29; H, 3.76; N, 6.54; found: C, 67.62; H,
3.75; N, 6.51%; UV/vis kmax (MeOH) 264, 277, 318 nm.
Yellowish solid, reaction time: 14 min, m.p. 248–250°C,
85% yield, recrystallization solvent: DMF; IR (KBr): t
3078 (w), 1655 (s, C=O), 1591 (s), 1442 (m), 1371 (s),
1272 (s), 1226 (s),1035 (s), 1008 (s), 754 (s, C–Cl), 682
1,10-(1,4-Phenylene)bis(3-(3-nitrophenyl)prop-2-en-1-one)
(3f)
1
(m) cm-1; H NMR (DMSO-d6, 300 MHz): dH 7.47–7.51
(m, 4H, H–Ar), 7.58-7.61 (d, 2H, J = 9.3 Hz, CO–CH),
8.07 (d, 4H, J = 3.12, H–Ar), 8.25–8.28 (d, 2H, J = 9.3,
C=CH), 8.33 (s, 4H, C6H4) ppm; 13C NMR (DMSO-d6,
75 MHz): dC 125.2, 128.2, 129.2, 129.5, 130.5, 132.6,
132.7, 134.9, 139.7, 140.9, 189.3 (C=O) ppm; Anal. Calcd.
for C24H16Cl2O2: C, 70.77; H, 3.96; found: C, 71.08; H,
3.94%; UV/vis kmax (MeOH) 262, 315 nm.
Light brown solid, reaction time: 12 min, m.p. 270–271°C,
94% yield, recrystallization solvent: DMF/H2O; IR (KBr): m
3086 (w), 1666 (s, C=O), 1608 (s), 1523, 1340 (s, –NO2),
1402 (w), 1330 (s), 1275 (m), 1221 (s), 1099 (w), 979 (m),
798 (m), 736 (s) cm-1; 1H NMR (DMSO-d6, 300 MHz): dH
7.77 (d, 2H, J = 8.0 Hz, H–Ar),7.89 (d, 2H, J = 15.7 Hz,
CO–CH), 8.18–8.30 (m, 4H, H–Ar, C=CH), 8.36 (s, 4H,
C6H4), 8.80 (s, 2H, H–Ar) ppm; Anal. Calcd. for
C24H16N2O6: C, 67.29; H, 3.76; N, 6.54; found: C, 67.65; H,
3.79; N, 6.51%; UV/vis kmax (MeOH) 261, 272, 306 nm.
1,10-(1,4-Phenylene)bis(3-(3-chlorophenyl)prop-2-en-1-
one) (3c)
1,10-(1,4-Phenylene)bis(3-(4-nitrophenyl)prop-2-en-1-one)
(3g)
Yellowish solid, reaction time: 12 min, m.p. 185–186°C,
88% yield, recrystallization solvent: DMF; IR (KBr): t
3041 (w), 1656 (s, C=O), 1606 (s), 1562 (m), 1415 (w),
1309 (m), 1224 (s), 1035 (w), 976 (m), 800 (m, C–Cl), 673
Brown crystalline solid, reaction time: 12 min, m.p.
305–307°C, 92% yield, recrystallization solvent: DMF; IR
(KBr): m 3109 (w), 1656 (s, C=O), 1593 (s), 1535, 1346 (s,
–NO2), 1413 (m), 1224 (s), 1109 (m), 1030 (m), 974 (m),
825 (s), 748 (s) cm-1; 1H NMR (DMSO-d6, 300 MHz): dH
7.85–7.95 (m, 4H, H–Ar, CO–CH), 8.14–8.36 (m, 12H, H–
Ar, C=CH, C6H4) ppm; Anal. Calcd. for C24H16N2O6: C,
67.29; H, 3.76; N, 6.54; found: C, 66.98; H, 3.75; N,
6.52%; UV/vis kmax (MeOH) 277, 307 nm.
1
(w) cm-1; H NMR (CDCl3, 300 MHz): dH 7.36–7.44 (m,
4H, H–Ar), 7.50–7.57 (m, 4H, H–Ar, CO–CH), 7.67 (s, 2H,
H–Ar), 7.76 (d, 2H, J = 15.7 Hz, C=CH), 8.15 (s, 4H,
C6H4) ppm; 13C NMR (CDCl3, 75 MHz): dC 122.9, 126.9,
128.0, 128.8, 130.3, 130.7, 135.1, 136.4, 141.1, 144.1,
189.5 (C=O) ppm; Anal. Calcd. for C24H16Cl2O2: C,
70.77; H, 3.96; found: C, 70.50; H, 3.94%; UV/vis kmax
(MeOH) 265, 314 nm.
1,10-(1,4-Phenylene)bis(3-(4-chlorophenyl)prop-2-en-1-
one) (3d)
1,10-(1,4-Phenylene)bis(3-(2-methoxyphenyl)prop-2-en-1-
one) (3h)
Yellow solid, reaction time: 10 min, m.p. 284–285°C, 91%
yield, recrystallization solvent: DMF/H2O; IR (KBr): m
3059 (w), 1656 (s, C=O), 1599 (s), 1489 (m), 1406 (m),
1327 (s), 1224 (s), 1091 (m), 1010 (s), 812 (s, C–Cl), 503
Dark yellow solid, reaction time: 18 min, m.p. 159–161°C,
81% yield, recrystallization solvent: EtOH/H2O; IR (KBr): m
3059 (w), 2947, 2839 (w, OCH3), 1657 (s, C=O), 1599 (s),
1491 (s), 1308 (m), 1248 (s), 1182 (s, C–OCH3), 748
1
(w) cm-1; H NMR (DMSO-d6, 300 MHz): dH 7.55 (d,
1
(s) cm-1; H NMR (CDCl3, 300 MHz): dH 3.93 (s, 6H,
4H, J = 7.56, H–Ar), 7.82 (d, 2H, J = 15.7, CO–CH),
7.95–7.98 (m, 6H, H–Ar, C=CH), 8.31 (s, 4H, C6H4) ppm;
Anal. Calcd. for C24H16Cl2O2: C, 70.77; H, 3.96; found: C,
70.43; H, 3.95%; UV/vis kmax (MeOH) 266, 324 nm.
2OCH3), 6.95–7.05 (m, 4H, H–Ar), 7.38 (t, 2H, J = 8.2 Hz,
H–Ar), 7.58–7.67 (m, 4H, H–Ar, CO–CH), 8.06–8.18 (m,
6H, C=CH, C6H4) ppm; 13C NMR (CDCl3, 75 MHz): dC
55.6 (OCH3), 111.3, 120.8, 122.7, 123.6, 128.3, 128.7, 129.4,
132.1, 141.3, 158.9 (C–OCH3), 190.8 (C=O) ppm; Anal.
Calcd. for C26H22O4: C, 78.37; H, 5.57; found: C, 78.66; H,
5.60%; UV/vis kmax (MeOH) 261, 280, 307, 362 nm.
1,10-(1,4-Phenylene)bis(3-(2-nitrophenyl)prop-2-en-1-one)
(3e)
1,10-(1,4-Phenylene)bis(3-(3-methoxyphenyl)prop-2-en-1-
one) (3i)
Brown solid, reaction time: 15 min, m.p. 254–256°C, 88%
yield, recrystallization solvent: DMF; IR (KBr) m 3109,
3063 (w), 1660 (s, C=O), 1595, 1344 (s, NO2), 1518 (s),
1411 (m), 1221 (s), 1109 (m), 985 (m), 827 (s), 750 (s), 540
Yellow solid, reaction time: 18 min, m.p. 165°C, 88%
yield, recrystallization solvent: DMF/H2O; IR (KBr): m
1
(m) cm-1; H NMR (DMSO-d6, 300 MHz): dH 7.75–8.11
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Med Chem Res (2012) 21:1811–1816
1815
3011 (w), 2941 (w, OCH3), 1656 (s, C=O), 1599 (s), 1493
(m), 1325 (m), 1255 (s, C–OCH3), 1168 (m), 1035 (s), 985
3059 (w), 1655 (s, C=O), 1604 (s), 1554 (s), 1475 (w),
1411 (m), 1325 (m). 1222 (s), 1035 (m), 976 (s), 835 (m),
;
798 (s, C–Br), 669 (m) cm-1 1H NMR (CDCl3,
1
(s), 831 (m), 788 (s), 678 (m) cm-1; H NMR (CDCl3,
300 MHz): dH 3.88 (s, 6H, 2OCH3), 6.99 (d, 2H,
J = 8.0 Hz, H–Ar), 7.18 (s, 2H, H–Ar), 7.26 (d, 2H,
J = 7.3 Hz, H–Ar), 7.37 (t, 2H, J = 8.0 Hz, H–Ar), 7.49
(d, 2H, J = 15.7 Hz, CO–CH), 7.84 (d, 2H, J = 15.7 Hz,
C=CH), 8.13 (s, 4H, C6H4) ppm; 13C NMR (CDCl3,
75 MHz): dC 55.4 (OCH3), 113.5, 116.6, 121.2, 122.1,
128.7, 130.0, 135.9, 141.2, 145.7, 160.0 (C–OCH3), 190.1
(C=O) ppm; Anal. Calcd. for C26H22O4: C, 78.37; H, 5.57;
found: C, 78.08; H, 5.58%; UV/vis kmax (MeOH) 261, 274,
314 nm.
300 MHz): dH 7.33 (t, 2H, J = 7.8 Hz, H–Ar), 7.51 (d, 2H,
J = 15.8 Hz, CO–CH), 7.57 (d, 4H, J = 8.2 Hz, H–Ar),
7.75 (d, 2H, J = 15.7 Hz, C=CH), 7.80 (d, 2H,
J = 9.1 Hz, H–Ar), 8.15 (s, 4H, C6H4) ppm; 13C NMR
(CDCl3, 75 MHz): dC 122.9, 123.2, 127.3, 128.8, 130.5,
130.9, 133.6, 136.7, 141.1, 144.0, 189.5 (C=O) ppm; Anal.
Calcd. for C24H16Br2O2: C, 58.09; H, 3.25; found: C,
58.38; H, 3.27%; UV/vis kmax (MeOH) 262, 315 nm.
1,10-(1,4-Phenylene)bis(3-(4-bromophenyl)prop-2-en-1-
one) (3m)
1,10-(1,4-Phenylene)bis(3-(4-methoxyphenyl)prop-2-en-1-
one) (3j)
Yellowish crystalline solid, reaction time: 10 min, m.p.
287–288°C, 94% yield, recrystallization solvent: DMF; IR
(KBr): m 3041 (w), 1656 (s, C=O), 1604 (s), 1487 (m), 1404
(m), 1224 (m), 1035 (m), 981 (m), 815 (s, C–Br), 497
Yellow solid, reaction time: 15 min, m.p. 217°C, 91%
yield, recrystallization solvent: benzene/MeOH; IR (KBr):
m 3067 (w), 2972, 2841 (w, OCH3), 1656 (s, C=O), 1593
(s), 1512 (s), 1425 (m), 1292 (s), 1235 (s), 1182 (s, C–
OCH3), 1031 (s), 987 (m), 810 (s), 563 (w) cm-1; 1H NMR
(CDCl3, 300 MHz): dH 3.88 (s, 6H, 2OCH3), 6.96 (d, 4H,
J = 7.4 Hz, H–Ar), 7.40 (d, 2H, J = 15.5 Hz, CO–CH),
7.63 (d, 4H, J = 7.3 Hz, H–Ar), 7.80 (d, 2H, J = 15.3 Hz,
C=CH), 8.12 (s, 4H, C6H4) ppm; 13C NMR (CDCl3,
75 MHz): dC 55.4 (OCH3), 114.5, 119.6, 127.4, 128.6,
130.4, 141.5, 145.6, 161.9 (C–OCH3), 190.1 (C=O) ppm;
Anal. Calcd. for C26H22O4: C, 78.37; H, 5.57; found: C,
78.66; H, 5.55%; UV/vis kmax (MeOH) 277, 357 nm.
1
(w) cm-1; H NMR (DMSO-d6, 300 MHz): dH 7.70 (m,
4H, H–Ar), 7.78–8.10 (m, 8H, H–Ar, CO–CH and C=CH),
8.31 (s, 4H, C6H4) ppm; Anal. Calcd. for C24H16Br2O2: C,
58.09; H, 3.25; found: C, 58.47; H, 3.24%; UV/vis kmax
(MeOH) 220, 234, 319 nm.
1,10-(1,4-Phenylene)bis(3-(2-hydroxyphenyl)prop-2-en-1-
one) (3n)
Yellow solid, reaction time: 25 min, m.p. 155–156°C, 94%
yield, recrystallization solvent: EtOH/H2O; IR (KBr): m
3254 (s, OH), 3041 (w), 1662 (s, C=O), 1575 (s), 1422 (m),
1334 (m), 1267 (s), 1211 (m), 991 (m), 758 (m), 594
1,10-(1,4-Phenylene)bis(3-(3,4-dimethoxyphenyl)prop-2-
en-1-one) (3k)
1
(w) cm-1; H NMR (DMSO-d6, 300 MHz): dH 6.85–6.97
(m, 4H, H–Ar), 7.26 (t, 2H, J = 7.2 Hz, H–Ar), 7.87–7.91
(m, 4H, H–Ar, CO–CH), 8.08 (d, 2H, J = 15.5 Hz,
C=CH), 8.23 (s, 4H, C6H4), 10.38 (s, 2H, OH) ppm; 13C
NMR (DMSO-d6, 75 MHz): dC 116.7, 119.9, 121.3, 121.7,
129.1, 129.3, 132.8, 140.8, 141.4, 157.9 (C–OH), 189.7
(C=O) ppm; Anal. Calcd. for C24H18O4: C, 77.82; H, 4.90;
found: C, 77.52; H, 4.89%; UV/vis kmax (MeOH) 306,
361 nm.
Yellow solid, reaction time: 15 min, m.p. 183–185°C, 85%
yield, recrystallization solvent: DMF/H2O; IR (KBr): m
3092 (w), 2935, 2837 (w, OCH3), 1662 (s, C=O), 1591 (s),
1516 (s), 1425 (m), 1265 (s, C–OCH3), 1141 (m), 1028
1
(m), 810 (w) cm-1; H NMR (CDCl3, 300 MHz): dH 3.83
(s, 6H, 2OCH3), 3.95 (s, 6H, 2OCH3), 6.91–6.94 (m, 4H,
H–Ar), 7.18 (d, 2H, J = 17.7 Hz, CO–CH), 7.71 (m, 2H,
H–Ar), 7.76 (d, 2H, J = 15.7 Hz, C=CH), 8.07 (s, 4H,
C6H4) ppm; 13C NMR (CDCl3, 75 MHz): dC 55.8 (OCH3),
56.0 (OCH3), 111.1, 119.7, 123.6, 127.5, 128.3, 128.6,
146.0, 147.8, 148.9, 149.2, 190.1 (C=O) ppm; Anal. Calcd.
for C28H26O6: C, 73.35; H, 5.72; found: C, 73.05; H,
5.70%; UV/vis kmax (MeOH) 274, 377 nm.
Biological screening
Preliminary experiments were carried out to determine the
antimicrobial activity in vitro of all compounds 3a–n by
using cup–plate agar method (Barry, 1976) at a concen-
tration of 400 lg/ml against staphylococcus aureus ATCC
29737, Escherichia coli ATCC 35218 and Candida albi-
cans ATCC 10231. The compounds were diluted in DMSO
for bioassay. The solvent control was included, although no
antibacterial and antifungal activity has been noted. All
1,10-(1,4-Phenylene)bis(3-(3-bromophenyl)prop-2-en-1-
one) (3l)
Yellow solid, reaction time: 15 min, m.p. 221°C, 85%
yield, recrystallization solvent: DMF/H2O; IR (KBr): m
123

1816
Med Chem Res (2012) 21:1811–1816
promoting compounds and for inhibitors of tumor promotion.
Cancer Lett 25:177–185
Hasegawa M, Saigo K, Mori T, Uno H, Nohara M, Nakanishi H
(1985) Topochemical ‘‘double’’ photocyclodimerization of the
samples were tested in triplicate and the average results
were recorded. The plates were incubated at 37°C for 24 h
to bacteria and incubated at 25°C for 48 h to fungus.
In addition, determination of the minimum inhibitory
concentration (MICs) values for the potent bis-chalcone
derivatives against three microorganisms using disc diffu-
sion method (Chand et al., 1994) was evaluated. In this
method, concentrations of 400, 200, 100, 50 and 25 lg/ml
used in per disc and incubated the same up conditions for
bacteria and fungus.
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Acknowledgments We are indebted to the Chemistry Department
of Arak University for providing of financial supports and also thank
the research council of Tehran University of Medical Sciences for the
evaluating of biological activities.
Mobinikhaledi A, Foroughifar N, Kalhor M, Mirabolfathy M (2010)
Synthesis and antifungal activity of novel 2-benzimidazolyli-
mino-5-arylidene-4-thiazolidinones. J Heterocycl Chem 47:77–
80
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