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European	Journal	of	Chemistry	4	(3)	(2013)	207‐210	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2013	EURJCHEM	

DOI:10.5155/eurjchem.4.3.207‐210.780	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Synthesis,	characterization	and	antibacterial	activity	of	(E)‐chalcone	derivatives

Ahmed	Mutanabbi	Abdula	

Chemistry	Department,	College	of	Science,	Al‐Mustansiriyah	University,	Baghdad,	00964,	Iraq	

*Corresponding	author	at:	Chemistry	Department,	College	of	Science,	Al‐Mustansiriyah	University,	Baghdad,	00964,	Iraq.	
Tel.:	+964.780.8838128;	fax:	+964.780.8838128.	E‐mail	address:	ahm.chem@yahoo.com	(A.M.	Abdula).	

	
	

	 	

	 	 	
ARTICLE	INFORMATION	 	 ABSTRACT
Received:	20	March	2013	
Received	in	revised	form:	23	April	2013	
Accepted:	23	April	2013	
Online:	30	September	2013	

KEYWORDS	

	 (E)‐Chalcone	derivatives	were	synthesized	by	 the	Claisen‐Schmidt	condensation	of	aromatic
aldehydes	with	methyl	 ketones.	 5‐Arylfuran‐2‐carboxaldehydes	 (1a‐b)	were	 synthesized	 by
Meerwein´s	method	and	condensed	with	2‐acetylpyrole	or	2‐acetylfuran	to	produce	the	new
chalcone	derivatives	 (2a‐d).	 The	new	chalcones	were	 characterized	using	 FT‐IR	and	GC‐MS.
The	 synthesized	 compounds	were	 also	 screened	 against	 some	 bacterial	 species	 to	 evaluate
their	activity	as	promising	antibacterial	agents.	

Furan	derivatives	
Meerwein’s	reaction	
Chalcone	derivatives	
Antibacterial	activity	
Claisen‐Schmidt	condensation	
1,3‐Diphenyl‐2‐propen‐1‐ones	

	
1.	Introduction	
	

Chalcones	 or	 1,3‐diphenyl‐2‐propen‐1‐one	 derivatives	 are	
a	class	of	open	chain	flavonoids	in	which	two	aromatic	rings	are	
linked	 by	 a	 three	 carbon	 α,β‐unsaturated	 carbonyl	 skeleton.	
Chalcones	and	 their	derivatives	have	 shown	a	wide	variety	of	
therapeutic	 activities	 such	 as	 anti‐oncogenic	 [1],	 anti‐
inflammatory	[2],	anti‐ulcerative	[3],	analgesic	[4],	antiviral	[5],	
anti‐fungal	 [6],	 anti‐malarial	 [7],	 and	 anti‐bacterial	 activities	
[8].	 During	 the	 last	 decade,	 the	 antimicrobial	 resistant	
represent	 the	major	problem	 facing	 the	world,	 so	 that	several	
new	antibiotics	and	antifungal	agents	are	accepted	each	year	to	
help	treatment	the	 infectious	diseases.	 In	order	to	discovering	
new	 antimicrobial	 agents,	 this	 research	 illustrated	 the	
synthesis	 novel	 (E)	 chalcone	 derivatives	 and	 screening	 their	
activities	 against	 some	 gram	 positive	 and	 game	 negative	
bacterial	species.		
	
2.	Experimental	
	
2.1.	Materials	and	method	
	

All	 starting	 materials	 and	 solvents	 were	 purchased	 from	
Sigma‐Aldrich	and	Fluka	and	used	without	further	purification.	
Melting	 points	 were	 determined	 on	 Electro‐thermal	 capillary	
apparatus	 and	 are	 uncorrected.	 FT‐IR	 measurements	 were	
recorded	on	Shimadzu	model	FT‐IR‐8400S.	Mass	spectra	were	
recorded	on	a	Shimadzu	GCMS‐QP2010	Ultra	apparatus.	
	
2.2.	General	procedure	for	the	preparation	of	5‐arylfuran‐2‐
carboxaldehydes	(1a‐b)	
	

These	 compounds	 were	 synthesized	 as	 mentioned	 in	 the	
reference	 [9,10].	 4‐Substituted	 aniline	 (0.136	 mol)	 was	
dissolved	in	a	mixture	of	concentrated	HCl	(33.7	mL)	and	H2O	
(22.5	mL).	The	solution	was	cooled	to	0	°C	and	diazotized	at	0‐5	
°C	with	sodium	nitrite	(9.5	g,	0.138	mol)	dissolved	 in	H2O	(25	

mL).	The	solution	was	stirred	 for	another	10	min,	filtered	and	
then	furan‐2‐carboxaldehyde	(15.4	g,	0.16	mol)	in	H2O	(50	mL)	
was	added	along	with	a	solution	of	CuCl2·2H2O	(5	g,	0.04	mol)	
in	 H2O	 (25	 mL)	 at	 a	 temperature	 of	 10‐15	 °C.	 The	 reaction	
mixture	 was	 slowly	 warmed	 up	 to	 40	 °C	 and	 stirred	 at	 this	
temperature	 for	 4h.	The	precipitate	was	 filtered	with	 suction,	
washed	 with	 water	 and	 an	 aqueous	 solution	 of	 sodium	
hydrogen	carbonate	(5%)	and	water.	The	products	were	dried	
at	room	temperature	and	recrystallized	 from	ethanol	(Scheme	
1).	
	
2.3.	General	procedure	for	the	preparation	of	(2E)‐3‐[5‐
(substituted	phenyl)‐furan‐2‐yl]‐1‐(aryl)prop‐2‐en‐1‐ones	
(2a‐d)	
	

These	derivatives	were	synthesized	according	to	procedure	
described	in	reference	[11‐14].	A	mixture	of	2‐acetylfuran	or	2‐
acetylpyrrol	 (0.004	mol),	 aromatic	 aldehyde	 (0.004	mol),	 and	
some	pellets	of	solid	NaOH	in	20	mL	of	ethanol	was	stirred	at	
room	 temperature	 for	 6	 h.	 The	 resulting	 solid	 was	 washed,	
dried,	and	crystallized	from	ethanol	(Scheme	1).		

(2E)‐3‐[5‐(4‐Chlorophenyl)‐furan‐2‐yl]‐1‐(1H‐pyrrol‐2‐yl)	
prop‐2‐en‐1‐one	 (2a):	 Color:	 Dark	 yellow	 powder.	 Yield:	 75%.	
M.p.:	158‐160	°C.	FT‐IR	(KBr,	ν,	cm‐1):	3229	(pyrrole	N‐H),	3132	
(aromatic	C‐H),	2969	 (aliphatic	C‐H),	1641	 (C=O),	1578,	1551	
(C=C).	GC‐MS	(EI,	m/z):	297	(M+),	186,	158,	139,	111,	94,	66,	44.	

(2E)‐3‐[5‐(3‐Nitrophenyl)‐furan‐2‐yl]‐1‐(1H‐pyrrol‐2‐yl)	
prop‐2‐en‐1‐one	 (2b):	 Color:	 Yellow	powder.	 Yield:	 73%.	M.p.:	
168‐170	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	 3241	 (pyrrole	 N‐H),	 3121	
(aromatic	C‐H),	2965,	2866	(aliphatic	C‐H),	1643	(C=O),	1589,	
1529	(C=C).	GC‐MS	(EI,	m/z):	308	(M+),	281,	207,	191,	186,	158,	
133,	96,	73,	44.	

(2E)‐3‐[5‐(4‐Chlorophenyl)‐furan‐2‐yl]‐1‐(furan‐2‐yl)prop‐2‐
en‐1‐one	 (2c):	Color:	Gray	powder.	Yield:	50%.	M.p.:	94‐96	°C.	
FT‐IR	(KBr,	ν,	cm‐1):	3123	(aromatic	C‐H),	2926,	2857	(aliphatic	
C‐H),	1651	(C=O),	1591,	1468	(C=C).	GC‐MS	(EI,	m/z):	298	(M+),	
263,	241,	187,	139,	111,	95,	76,	67.	



208	 Abdula	/	European	Journal	of	Chemistry	4	(3)	(2013)	207‐210	
	

	

 
	

Scheme	1
	
	

 

Scheme	2	
	
	

	
	
(2E)‐3‐[5‐(3‐Nitrophenyl)‐furan‐2‐yl]‐1‐(furan‐2‐yl)prop‐2‐

en‐1‐one	 (2d):	 Color:	 Dark	 brown	 powder.	 Yield:	 40%.	 M.p.:	
115‐118	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	 3124	 (aromatic	 C‐H),	 2928,	
2862	(aliphatic	C‐H),	1665	(C=O),	1597,	1528(C=C).	GC‐MS	(EI,	
m/z):	308	(M+),	281,	207,	191,	158,	133,	96,	73,	44.	

	
2.4.	Antimicrobial	studies	
	

The	 (E)‐chalcone	 derivatives	 (2a‐d)	 were	 tested	 for	 their	
antibacterial	 activity	 against	 Escherichia	 coli,	 Klebsiella	 SPP	
(Gram	 ‐)	 as	 well	 as	 Staphylococcus	 aureus	 and	 Enterococcus	
faecalis	 (Gram	+)	using	well	diffusion	method	[15].	DMSO	was	
run	 as	 a	 control	 and	 test	 was	 performed	 at	 10	 mg/mL	
concentration	using	DMSO	solvent.	Tetracycline	and	amoxicillin	
were	 used	 as	 standard	 drugs.	 Each	 experiment	 was	 made	 in	
triplicate	and	the	average	reading	was	taken.	

	
	

3.	Results	and	discussion	
		

The	 starting	 materials	 5‐(4‐chlorophenyl)furan‐2‐carbox‐
aldehyde	 (1a)	 and	 5‐(3‐nitrophenyl)furan‐2‐carboxaldehyde	
(1b)	 were	 prepared	 under	 the	 conditions	 of	 Meerwein´s	
reaction	 from	 4‐chloroaniline	 or	 3‐nitroaniline	 and	 furan‐2‐
carboxaldehyde	 as	 described	 in	 Scheme	 1.	 Claisen‐Schmidt	
condensation	of	aldehyde	derivatives	(1a‐b)	with	2‐acetylfuran	
or	 2‐acetylpyrrol	 in	 the	 presence	 of	 sodium	 hydroxide	 gives	
chalcone	derivatives	2a‐d	in	good	yield	(Scheme	1).	

The	 mechanism	 of	 Claisen‐Schmidt	 reaction	 can	 be	
summarized	in	Scheme	2.	

The	 structures	 of	 chalcone	 derivatives	 (2a‐d)	 were	
characterized	by	recording	their	IR	and	GC‐MS	spectra.	The	IR	
spectrum	 of	 compound	 2a	 showed	 absorption	 at	 3229	 cm‐1	
which	is	due	to	the	pyrrole	N‐H	stretching,	while	the	aromatic	
C‐H	stretching	frequency	absorption	appear	at	3132	cm‐1.		

	

5.0 7.5 10.0 12.5 15.0 17.5 20.0 22.5 25.0 27.5 30.0 32.5

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

1.1

1.2

(x1,000,000)
TIC

	
a	

50.0 75.0 100.0 125.0 150.0 175.0 200.0 225.0 250.0 275.0 300.0 325.0 350.0
0

10

20

30

40

50

60

70

80

90

100

%

158

297

139

20713094
66 111 268204 28144 186

233
254 355

	
b	

	
Figure	1.	GC	spectra	(a)	and	GC‐MS	spectra	(b)	of	chalcone	derivative	2a.	

N
H

O

O

Cl



Abdula	/	European	Journal	of	Chemistry	4	(3)	(2013)	207‐210	 209	
 

	
Table	1.	Inhibition	zone	of	(E)‐chalcone	derivatives	against	some	bacterial	species.	

Compound	
Inhibition	zone	(mm)	at	10	mg/mL	against

Gram	(‐) Gram	(+)	
Escherichia	coli	 Klebsiella	SPP Staphylococcus	aureus Enterococcus	faecalis

2a	 ‐	 ‐ ‐ ‐	
2b	 10	 7 22 ‐	
2c	 ‐	 ‐	 28	 ‐	
2d	 8	 7	 14	 ‐	
Tetracycline	 19	 10 ‐ 20	
Amoxicillin	 ‐	 8	 30	 19	

	
	

O

O

HN
Cl

O

HN

m/z =94

HN

m/z = 66

O

O

HN

O
HN

O

O
HN

m/z = 186

m/z = 158

m/z = 297

 
	

Figure	2.	Mass	fragments	of	compound	2a.
	
	
The	 aliphatic	 C‐H	 sterching	 appear	 at	 2969	 cm‐1.	 The	

carbonyl	 group	 C=O	 frequency	 band	 appeared	 at	 1641	 cm‐1.	
Bands	at	1578	and	1551	cm‐1	related	to	C=C	absorption	further	
confirm	the	structure	of	compound.		

The	GC‐MS	spectrum	of	2a	as	illustrated	in	Figure	1	showed	
the	 parent	 ion	 peak	 at	 an	 m/z	 value	 of	 297	 (M+)	 and	 the	
fragments	 at	 186,	 158,	 94	 and	 66	 strongly	 enhanced	 the	
elucidation	of	compound.	The	physical	properties,	spectral	data	
and	mass	analysis	of	all	 the	synthesized	compounds	are	given	
in	the	experimental	section.	

The	suggested	fragments	for	the	compound	2a	depicted	in	
Figure	2.	

This	research	included	the	in	vitro	assay	of	the	synthesized	
compounds	against	several	microbial	 species	 to	evaluate	 their	
activities	 as	 promising	 antimicrobial	 agents.	 The	 antibacterial	
activity	 results	 revealed	 that	 (2E)‐3‐[5‐(substituted	 phenyl)‐
furan‐2‐yl]‐1‐(aryl)prop‐2‐en‐1‐ones	 (2a‐d)	 exhibited	
moderate	 to	 potent	 bacterial	 growth	 inhibition	 against	 some	
gram	 positive	 and	 gram	 negative	 strains.	 Compound	 2c	
exhibited	the	portentous	activity	against	Staphylococcus	aureus	
comparing	 with	 Amoxicillin	 as	 standard	 while	 compound	 1	
show	no	activity	against	all	bacterial	species.	Table	1	shows	the	
Inhibition	 zone	 in	mm	 at	 10	mg/	mL	 concentration	 of	 tested	
compounds.	
	
4.	Conclusions	
	

(E)‐Chalcone	 derivatives	 were	 prepared	 by	 the	 Claisen‐
Schmidt	 condensation.	 The	 synthesized	 derivatives	 were	
confirmed	 using	 FT‐IR	 and	 GC‐MS	 analysis.	 The	 new	
compounds	were	 tested	 against	 several	 of	 gram	 positive	 and	

gram	 negative	 bacterial	 species	 and	 exhibited	 potent	 to	
moderate	activity	as	antimicrobial	species.	
	
Acknowledgements	
	

This	 study	 was	 supported	 by	 Chemistry	 Department,	
College	of	Science,	Al‐Mustansiriyah	University,	Baghdad,	Iraq.	
	
Supplementary	Materials:	 FT‐IR	 and	 GC‐MS	 data	 for	 comp‐
ounds	 2a‐d.	 This	 material	 is	 available	 free	 of	 charge	 via	 the	
Internet	at	http://www.eurjchem.com.	
	
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