Design and synthesis of new imidazolinone derivatives as potential antifungal agents

Article abstract of DOI:10.1002/jhet.588

A new series of chalcones, pyrimidines, and imidazolinone is described; chalcones (4a-o) were prepared from the lead 4-[2-(5-ethylpyridin-2-yl)ethoxy] benzaldehyde. Pyrimidines (5a-o) were prepared from the reaction of chalcones and guanidine nitrate in a

Full text of DOI:10.1002/jhet.588

March 2011
Design and Synthesis of New Imidazolinone Derivatives as
Potential Antifungal Agents
373
Navin B. Patel* and Hemant R. Patel
Department of Chemistry, Veer Narmad South Gujarat University, Surat 395007, India
*E-mail: drnavin@satyam.net.in
Received March 14, 2010
DOI 10.1002/jhet.588
Published online 22 December 2010 in Wiley Online Library (wileyonlinelibrary.com).
A new series of chalcones, pyrimidines, and imidazolinone is described; chalcones (4a–o) were prepared
from the lead 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde. Pyrimidines (5a–o) were prepared from the
reaction of chalcones and guanidine nitrate in alkali media. Imidazolinones (6a–o) were synthesized from
the reaction of pyrimidine and oxazolone derivatives (prepared by Erlenmeyer azlactone synthesis). The
1
structures of the synthesized compounds were assigned on the basis of elemental analyses, IR, H-NMR,
and 13C-NMR spectral data. All the products were screened against different strains of bacteria and fungi.
Most of these compounds showed better inhibitory activity in comparison with the standard drugs.
J. Heterocyclic Chem., 48, 373 (2011).
INTRODUCTION
reported to possess fungicidal activities [8], herbicidal
activities [9], vasodilator activities [10], anticonvulsant
agents [11], and antitumor agent [12].
Heterocyclic compounds are acquiring more impor-
tance in recent years because of their pharmacological
activities. Nitrogen and oxygen containing five- and six-
membered heterocyclic compounds have occupied enor-
mous significance in the field of medicinal chemistry.
The basic nucleus imidazole emerges from the drug
intermediate azlactone. The azlactones possess oxazo-
lone moiety. They are also of great importance to pro-
duce penicillin type of drug intermediates and also use-
ful to produce synthetic hormonal compounds. Imidaz-
ole is a planer five-membered heterocyclic ring system
with three carbon and two nitrogen atoms in 1 and 3
positions; imidazolones are keto dihydro imidazoles and
are known as oxoimidazoline; a five-membered hetero-
cyclic ring system having nitrogen atoms in 1 and 3
positions and carbonyl at 5 position. Oxoimidazoline,
also known as imidazolinone, is reported to exhibit a
wide variety of antibacterial [1,2], antifungal [3], and
antimicrobial activities [4–7]. They have also been
Recently, we have prepared chalcones, pyrimidines,
and amide derivatives and studied their antibacterial and
antifungal activities [13,14]. In continuation of our work
on chalcones and pyrimidines, we planned to attach oxa-
zolones with amino group of pyrimidine and to synthe-
size imidazolinone derivatives.
Hence, with a view to further assess the pharmacolog-
ical profile of this class of compounds, it was thought
worthwhile to synthesize some new congeners of imida-
zolinone heterocycles by incorporating the chalcone and
pyrimidine moieties in a single molecular framework.
RESULTS AND DISCUSSION
Chemistry. The synthesis of chalcones, pyrimidines,
and imidazolinone derivatives was performed following
the steps shown in Scheme 1. In the initial step,
C
V
2010 HeteroCorporation

374
N. B. Patel and H. R. Patel
Vol 48
Scheme 1. Synthesis of compounds 5a–o and 6a–o.
chalcones 4a–o were synthesized by condensing 4-[2-(5-
ethylpyridin-2-yl)ethoxy]benzaldehyde with appropriate ar-
omatic acetophenones in diluted methanolic sodium hy-
droxide solution at room temperature. The compounds 5a–
o were synthesized by the reaction of an appropriate chal-
cone with guanidine nitrate and sodium ethoxide solution.
Compounds 6a–o were prepared from the reaction of pyri-
midines and oxazolones. The purity of the compounds was
determined by thin layer chromatography (TLC) and ele-
mental analyses. Spectral data (IR, 1H-NMR, and 13C-
NMR) of all the newly synthesized compounds were in full
agreement with the proposed structures.
The synthesis of 4a–o was confirmed by the IR and
NMR spectra. In the IR spectrum, the sharp band of
AC¼¼O was observed at 1662 cmꢀ1, ACH¼¼CHA of
chalcone was observed at 1599 cmꢀ1, the asymmetric
and symmetric band of CAOAC ether linkage in the
structure were observed at 1223 and 1036 cmꢀ1. The
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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Design and Synthesis of New Imidazolinone Derivatives as
Potential Antifungal Agents
375
1
H-NMR spectra exhibited one doublet at d 7.11 attrib-
uted to the ¼¼CHACOA protons and two protons with
triplet at d 4.32 confirmed that ACH2AOA. In the 13C-
NMR spectra of chalcones, the higher field resonances
at d 190.0 ppm were attributed to the carbonyl group
present in chalcone. The structures of compounds 5a–o
and 6a–o were also established by using IR and NMR
spectroscopy. The IR spectra of pyrimidine showed dis-
appearance of AC¼¼O band at 1662 cmꢀ1 and appear-
ance of asymmetric and symmetric new broad bands at
3355 cmꢀ1 and 3220 cmꢀ1 for ANH2, respectively. A
signal at d 5.15 and d 7.85 for the ANH2 and ACH of
stock solution. In primary screening, 500, 250 and 125 lg/
mL concentrations of the synthesized drugs were taken.
The active synthesized drugs found in this primary screen-
ing were further tested in a second set of dilution against
all microorganisms. The drugs found active in primary
screening were similarly diluted to obtain 100, 50, 25,
12.5, 6.250, 3.125, and 1.5625 lg/mL concentrations. The
highest dilution showing at least 99% inhibition is taken as
MIC.
The MICs of synthesized compounds were carried out
by broth microdilution method as described by Rattan
[15]. Antibacterial activity was screened against two
Gram-positive (Staphylococcus aureus MTCC 96, Strep-
tococcus pyogenus MTCC 443) and two Gram-negative
(Escherichia coli MTCC 442, Pseudomonas aeruginosa
MTCC 441) bacteria, in which ampicillin was used as a
standard antibacterial agent. Antifungal activity was
screened against three fungal species Candida albicans
MTCC 227, Aspergillus niger MTCC 282, and Aspergil-
lus clavatus MTCC 1323, in which greseofulvin was
used as a standard antifungal agent.
13
pyrimidine ring, respectively, was observed, and the C-
NMR spectra of pyrimidine ACH appeared at d 103.2.
The sharp band of AC¼¼O in imidazolinone was
observed at 1797 cmꢀ1 and another band of AC¼¼N
was observed at 1656 cmꢀ1. The H-NMR spectra
1
showed a signal at 7.30 with singlet that determined the
13
ACH group of imidazolinone, and the C-NMR spectra
carbon of AC¼¼O appeared at 170.4.
From the above spectral analysis, we have confirmed
the conversion of chalcones to pyrimidines and the con-
version of pyrimidines to imidazolinones derivatives.
Antimicrobial activity. Methods. All microbial type
culture collection (MTCC) cultures were collected from
the Institute of Microbial Technology, Chandigarh, and
tested against the known drugs ampicillin and greseofulvin.
Mueller Hinton broth was used as nutrient medium to grow
and dilute the drug suspension for the test. Inoculum size
for test strain was adjusted to 108 colony-forming unit per
milliliter by comparing the turbidity. DMSO was used as
diluents to get desired concentration of drugs to test on
standard bacterial strains. Serial dilutions were prepared in
primary and secondary screening. The control tube contain-
ing no antibiotic was immediately subcultured (before
inoculation) by spreading a loopful evenly over a quarter
of plate of medium suitable for the growth of the test orga-
nism and kept for incubation at 37ꢁC overnight. The tubes
were then incubated overnight. The minimum inhibition
concentrations (MIC) of the control organism was read to
check the accuracy of the drug concentrations. The lowest
concentration inhibiting growth of the organism was
recorded as the MIC. All the tubes not showing visible
growth (in the same manner as control tube described
above) was subcultured and incubated overnight at 37ꢁC.
The amount of growth from the control tube before incuba-
tion (which represents the original inoculum) was com-
pared. Subcultures might show similar number of colonies
indicating bacteriostatic, a reduced number of colonies
indicating a partial or slow bactericidal activity, and no
growth if the whole inoculum has been killed. The test
must include a second set of the same dilutions inoculated
with an organism of known sensitivity. Each synthesized
drug was diluted obtaining 2000 lg/mL concentration, as a
Antibacterial activity. The minimal bactericidal con-
centrations (MBCs) of the tested compounds are shown
in Table 1. The different compounds 4a–o, 5a–o, and
6a–o were tested in in vitro against two Gram-positive
(S. aureus MTCC 96, S. pyogenus MTCC 443) and two
Gram-negative (E. coli MTCC 442, P. aeruginosa
MTCC 441) bacteria. From the screening data, chal-
cones, 4b, 4f, and 4h showed MBC value in the range
between 62.5 and 100 lg/mL while ampicillin has
standard MBC value of 100 lg/mL against E. coli
which indicates that these compounds have excellent ac-
tivity, while other chalcones 4c, 4d and 4o possessed
MBC value in the range of 125–150 lg/mL against E.
coli, and 4h exhibited very good activity against P. aer-
uginosa. Compounds 4f and 4h displayed excellent ac-
tivity in the range of 100–150 lg/mL while remaining
4b, 4d and 4n were equivalent against S. aureus when
compared with ampicillin. Compound 4h have MBC
value of 150 lg/mL, which was comparatively good
against S. pyogenus. The remaining chalcones possessed
moderate to poor activity against all four bacterial spe-
cies. In the pyrimidine derivatives, compound 5b pos-
sessed MBC value of 62.5 lg/mL against E. coli and
MBC value of 150 lg/mL against P. aeruginosa, which
was comparable with ampicillin. Compound 5e exhib-
ited MBC value of 150 lg/mL against P. aeruginosa.
Compound 5h showed MBC value of 100 lg/mL
against S. aureus and MBC value of 100 lg/mL against
S. pyogeneus. Compound 5i possessed MBC value of
62.5 lg/mL against E. coli and MBC value of 150 lg/
mL against S. aureus, which showed that this compound
is as active as ampicillin. Compound 5l showed MBC
value of 100 lg/mL against P. aeruginosa and MBC
Journal of Heterocyclic Chemistry
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376
N. B. Patel and H. R. Patel
Vol 48
Table 1
Antimicrobial activities of compounds 4a–o, 5a–o, and 6a–o.
Minimal bactericidal concentration (lg/mL)
Minimal fungicidal
concentration (lg/mL)
Gram negative
Gram positive
Compound
R
E. coli
P. aeruginosa
S. aureus
S. pyogenus
C. albicans
A. niger
A. clavatus
4a
2,4-Cl,5-F
4-OCH3
2,4-Cl
4-OH
2,6-Cl,5-F
4-CH3
-H
200
100
150
150
500
100
500
250
150
500
200
250
150
1000
100
250
500
500
250
500
500
250
250
150
500
200
150
200
250
250
150
250
250
100
250
500
500
250
250
200
100
500
250
250
150
250
250
200
250
250
500
1000
1
1000
250
500
250
500
100
1000
150
500
500
1000
500
1000
250
500
500
250
250
500
1000
250
500
100
150
200
250
150
500
250
500
500
250
250
500
500
500
1000
200
250
250
250
1000
1000
500
250
1000
250
500
250
1000
250
1000
150
500
250
1000
250
1000
500
500
500
250
500
500
1000
250
500
100
200
200
250
250
500
250
250
1000
250
500
500
500
1000
1000
200
500
250
250
150
1000
250
250
0.5
1000
1000
500
500
1000
1000
200
250
1000
1000
1000
1000
500
500
1000
500
500
500
500
500
500
500
500
500
1000
1000
500
1000
500
200
>1000
500
1000
500
500
500
500
1000
1000
200
500
500
1000
1000
1000
–
500
1000
500
500
500
500
1000
1000
1000
500
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
4m
4n
4o
5a
5b
5c
5d
5e
5f
5g
5h
5i
5j
5k
5l
5m
5n
5o
6a
6b
6c
6d
6e
6f
6g
6h
6i
6j
6k
6l
6m
6n
6o
1000
500
1000
500
4-F
2,4-F
62.5
>1000
1000
>1000
>1000
500
>1000
250
500
500
500
500
250
125
150
1000
>1000
>1000
500
4-Br
3,4-Cl
4-Cl
3-OCH3
3-F
3,4-F
2,4-Cl,5-F
4-OCH3
2,4-Cl
4-OH
2,6-Cl,5-F
4-CH3
-H
4-F
2,4-F
4-Br
3,4-Cl
4-Cl
500
500
1000
1000
500
1000
1000
1000
>1000
>1000
1000
500
62.5
>1000
>1000
500
500
250
250
200
250
250
500
500
500
500
250
500
250
62.5
1000
1000
500
1000
1000
500
250
250
250
250
500
250
250
500
250
100
250
200
200
100
100
200
250
150
200
1000
1000
500
500
500
500
3-OCH3
3-F
3,4-F
1000
200
1000
200
2,4-Cl,5-F
4-OCH3
2,4-Cl
4-OH
2,6-Cl,5-F
4-CH3
-H
>1000
500
500
>1000
500
500
500
500
>1000
1000
>1000
500
>1000
200
>1000
1000
>1000
500
>1000
200
4-F
2,4-F
4-Br
3,4-Cl
4-Cl
1000
1000
1000
500
1000
>1000
1000
1000
1000
–
3-OCH3
3-F
3,4-F
1000
–
Gentamycin
Ampicillin
Chloramphenicol
Ciprofloxacin
Norfloxacin
Nystatin
Greseofulvin
0.05
0.25
100
50
25
10
–
100
50
25
10
250
50
50
10
–
100
50
50
10
–
–
–
–
–
–
–
–
–
–
100
500
–
100
100
–
100
100
–
–
–
–
–
–
value of 150 lg/mL against S. aureus. The remaining pyr-
imidines displayed moderate to poor activities against all
four bacterial species. For the imidazolinone derivatives,
compounds 6h and 6i showed MBC value of 100 lg/mL
against E. coli. Compound 6d showed MBC value of 100
lg/mL against E. coli and P. aeruginosa, which was as
active as ampicillin; against S. aureus, compounds 6b, 6c,
6i, 6j, 6k, and 6o gave MBC value of 250 lg/mL, which
Journal of Heterocyclic Chemistry
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March 2011
Design and Synthesis of New Imidazolinone Derivatives as
Potential Antifungal Agents
377
Scheme 2. Synthesis of oxazol-5(4H)-one.
6d, 6e, 6f, 6g, 6k, and 6l are said to be as active as gre-
seofulvin when they were tested with C. albicans. Com-
pound 6j displayed excellent activity of 200 lg/mL
against C. albicans. From these results, it is concluded
that the imidazolinone derivatives showed good antifun-
gal activity rather than antibacterial activity.
EXPERIMENTAL
Laboratory chemicals were supplied by Rankem India Ltd.,
New Delhi, India and Ficher Scientific UK Ltd., Loughbor-
ough, Leicestershire. Melting points were determined by the
open-tube capillary method and are uncorrected. The purity of
the compounds was determined by TLC plates (silica gel G) in
the solvent system, i.e., toluene:ethyl acetate (75:25). The
spots were observed by exposure to iodine vapors or by UV
light. The IR spectra were obtained on a Perkin-Elmer 1720
1
FTIR spectrometer (KBr pellets). The H-NMR and 13C-NMR
spectra were recorded on a Bruker Avance II 400 spectrometer
using TMS as the internal standard in CDCl3. Elemental analy-
ses of the newly synthesized compounds were carried out on
Carlo Erba 1108 analyzer.
shows that these compounds are as active as ampicillin.
Compound 6h is said to be more active when it was
tested against S. aureus. Imidazolinones are moderately
active against S. pyogeneus.
Procedure for the synthesis of 4-[2-(5-ethylpyridin-2-yl)e-
thoxy]benzaldehyde
(3). 4-[2-(5-Ethylpyridin-2-yl)ethoxy]-
benzaldehyde (3) was synthesized by the method described in
refs. 16 and 17.
Antifungal activity. Minimal fungicidal concentra-
tions (MFCs) of the synthesized compounds are shown
in Table 1. For in vitro antifungal activity, three fungal
species C. albicans MTCC 227, A. niger MTCC 282,
and A. clavatus MTCC 1323 were used and compared
with greseofulvin. Most of the compounds possessed
very good antifungal activity against C. albicans when
they were compared greseofulvin; their MFC values
were in the range between 100 and 500 lg/mL. For
chalcones, compounds 4g and 4h showed excellent
activities of 200–250 lg/mL; 4c, 4d, 4m, and 4n pos-
sessed very good activity of 500 lg/mL, which is simi-
lar to greseofulvin (500 lg/mL) against C. albicans,
whereas chalcones possessed moderate to poor activity
against A. niger and A. clavatus. For pyrimidines, com-
pound 5o possessed good activity of 200 lg/mL against
C. albicans, which showed that this compound is more
active when compared with greseofulvin (500 lg/mL);
whereas for imidazolinone derivatives, compound 6j dis-
played excellent activity of 200 lg/mL against C. albi-
cans, A. niger, and A. clavatus, which indicates that this
compound is very active when compared with greseoful-
vin; while rest of the compounds 6b, 6d, 6e, 6f, 6g, 6k,
and 6l possessed MFC value of 500 lg/mL against C.
albicans, which have similar values like greseofulvin.
General preparation of the compounds 4a–o. Chalcones
were synthesized and characterized by the method described in
ref. 13.
General preparation of the compounds 5a–o. Pyrimidines
were synthesized and characterized by the method described in
ref. 13.
General process of oxazol-5(4H)-one (Erlenmeyer azlac-
tone synthesis) (C). A mixture of 3,4,5-trimethoxy benzalde-
hyde (0.33 mol), hippuric acid (0.33 mol), and potassium ace-
tate (0.33 mol) in acetic anhydride (0.83 mol) was refluxed
with stirring for 15 min [reaction progress was monitored by
TLC using isohexane:ethyl acetate (3:1) as eluent]. The mix-
ture was then cooled and neutralized by the addition of solid
potassium carbonate. The solid product was separated by filtra-
tion, dried, and purified from ethanol (as shown in Scheme 2).
CONCLUSION
Chalcones and pyrimidine derivatives possessed very
good activity against all four bacterial species, but the
observed results for fungicidal species are satisfactory.
In the case of imidazolinone derivatives, compounds 6b,
Figure 1. Imidazolinones 6a–o.
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N. B. Patel and H. R. Patel
Vol 48
General preparation of the compounds 6a–o. A mixture
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(4-hydroxy
phenyl) pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6d). This compound was
obtained as yellow solid, yield 57%, m.p. 215–217ꢁC, Rf:
0.61; IR (KBr): Ar-H 3065, OH 3354, CH2 2953, 2833, C¼¼O
of imidazolinone 1795, C¼¼N imidazolinone 1652, C¼¼N of
of 5a–o (0.01 mol) and an appropriate oxazolone (0.01 mol) in
50 mL acetic acid was refluxed for 6–8 h [reaction progress
was monitored by TLC using toluene–ethyl acetate (7.5:2.5) as
eluent]. After completion of reaction, the resulted mixture was
cooled and poured into ice cold water and the formed precipi-
tate was filtered and washed with water till pH neutral. The
raw product was crystallized from ethanol (Fig. 1).
pyrimidine 1612, CAOAC 1224, 1032 cmꢀ1 1H-NMR (deu-
;
teriochloroform): d 1.17 (t, 3H, J ¼ 7.63 Hz, ACH3), 2.54 (q,
2H, J ¼ 7.63 Hz, ACH2A), 3.24 (t, 2H, J ¼ 6.72 Hz, ACH2),
3.83 (s, 3H, AOCH3), 4.36 (t, 2H, J ¼ 6.71 Hz, ACH2AO),
6.78–8.35 (m, 19H, pyridine, pyrimidine, and Ar-H), 9.85 (s,
1H, AOH); 13C-NMR (CDCl3): d 15.6 (C8), 25.7 (C7), 37.5
(C9), 56.4 (C48–C50), 67.4 (C10), 103.7 (C22), 103.6–150.4
(C36–C41), 108.3 (C35), 114.7–157.6 (C11–C16), 122.3–157.4
(C2–C6), 126.5–130.8 (C42–C47), 116.4–158.5 (C23–C28), 130.6
(C32), 160.2 (C21), 163.6 (C17), 164.1 (C34), 169.5 (C19), 170.9
(C31). Anal. Calcd for C44H39N5O6: C, 72.02; H, 5.36; N,
9.54. Found: C, 72.04; H, 5.35; N, 9.52.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(2,4-dichloro-
5-fluoro phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxy-
benzylidene)-1H-imidazol-5(4H)-one (6a). This compound
was obtained as brown solid, yield 54%, m.p. 115–119ꢁC, Rf:
0.62; IR (KBr): Ar-H 3063, CH2 2952, 2834, C¼¼O of imida-
zolinone 1797, C¼¼N imidazolinone 1655, C¼¼N of pyrimidine
1613, CAOAC 1223, 1035, CAF 973, CACl 744 cmꢀ1 1H-
;
NMR (deuteriochloroform): d 1.20 (t, 3H, J ¼ 7.63 Hz,
ACH3), 2.51 (q, 2H, J ¼ 7.62 Hz, ACH2A), 3.26 (t, 2H, J ¼
6.71 Hz, ACH2), 3.82 (s, 3H, AOCH3), 4.35 (t, 2H, J ¼ 6.71
Hz, ACH2AO), 6.76–8.33 (m, 17H, pyridine, pyrimidine, and
Ar-H); 13C-NMR (CDCl3): d 15.2 (C8), 25.2 (C7), 37.5 (C9),
56.4 (C48–C50), 67.4 (C10), 103.3 (C22), 103.8–150.4 (C36–
C41), 108.4 (C35), 114.8–157.3 (C11–C16), 122.3–157.3 (C2–
C6), 126.3–130.0 (C42–C47), 118.7–1161.4 (C23–C28), 130.4
(C32), 160.2 (C21), 163.6 (C17), 164.2 (C34), 169.5 (C19), 170.8
(C31). Anal. Calcd for C44H36N5O5Cl2F: C, 65.67; H, 4.51; N,
8.70. Found: C, 65.63; H, 4.50; N, 8.68.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(2,6-dichlouro-
5-flouro phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxyben-
zylidene)-1H-imidazol-5(4H)-one (6e). This compound was
obtained as brown solid, yield 56%, m.p. 103–105ꢁC, Rf: 0.60;
IR (KBr): Ar-H 3058, CH2 2958, 2837, C¼¼O of imidazolinone
1789, C¼¼N imidazolinone 1653, C¼¼N of pyrimidine 1617,
CAOAC 1223, 1035, CAF 972, CACl 745 cmꢀ1 1H-NMR
;
(deuteriochloroform): d 1.16 (t, 3H, J ¼ 7.63 Hz, ACH3), 2.50
(q, 2H, J ¼ 7.63 Hz, ACH2A), 3.25 (t, 2H, J ¼ 6.72 Hz,
ACH2), 3.83 (s, 3H, AOCH3), 4.34 (t, 2H, J ¼ 6.71 Hz,
ACH2AO), 6.78–8.35 (m, 17H, pyridine, pyrimidine, and Ar-
H); 13C-NMR (CDCl3): d 15.8 (C8), 25.8 (C7), 37.2 (C9), 56.4
(C48–C50), 67.4 (C10), 103.2 (C22), 103.5–150.4 (C36–C41),
108.7 (C35), 115.1–157.1 (C11–C16), 122.3–157.4 (C2–C6),
126.3–130.6 (C42–C47), 118.3–161.4 (C23–C28), 130.1 (C32),
160.7 (C21), 163.4 (C17), 164.5 (C34), 169.0 (C19), 170.6 (C31).
Anal. Calcd for C44H36N5O5Cl2F: C, 65.67; H, 4.51; N, 8.70.
Found: C, 65.61; H, 4.50; N, 8.73.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(4-methoxy
phenyl) pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6b). This compound was
obtained as brown solid, yield 65%, m.p. 110–112ꢁC, Rf: 0.64; IR
(KBr): Ar-H 3064, CH2 2951, 2833, C¼¼O of imidazolinone
1792, C¼¼N imidazolinone 1655, C¼¼N of pyrimidine 1614,
CAOAC 1223, 1032 cmꢀ1 1H-NMR (deuteriochloroform): d
;
1.19 (t, 3H, J ¼ 7.62 Hz, ACH3), 2.53 (q, 2H, J ¼ 7.62 Hz,
ACH2A), 3.23 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.83 (s, 3H,
AOCH3), 4.34 (t, 2H, J ¼ 6.71 Hz, ACH2AO), 6.78–8.35 (m,
19H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.5
(C8), 25.3 (C7), 37.2 (C9), 55.8 (C29), 56.3 (C48–C50), 67.4 (C10),
103.2 (C22), 103.5–150.7 (C36–C41), 108.2 (C35), 114.5–157.6
(C11–C16), 122.1–157.4 (C2–C6), 126.5–130.1 (C42–C47), 114.8–
160.6 (C23–C28), 130.2 (C32), 160.6 (C21), 163.3 (C17), 164.3
(C34), 169.1 (C19), 170.3 (C31). Anal. Calcd for C45H41N5O6: C,
72.27; H, 5.53; N, 9.36. Found: C, 72.25; H, 5.51; N, 9.34.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(4-methyl
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6f). This compound was
obtained as dark brown solid, yield 61%, m.p. 200–203ꢁC, Rf:
0.65; IR (KBr): Ar-H 3063, CH2 2953, 2835, C¼¼O of imida-
zolinone 1797, C¼¼N imidazolinone 1656, C¼¼N of pyrimidine
1614, CAOAC 1222, 1034 cmꢀ1 1H-NMR (deuteriochloro-
;
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(2,4-dichloro
phenyl) pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6c). This compound was
obtained as yellow solid, yield, 58%, m.p. 113–115ꢁC, Rf:
0.59; IR (KBr): Ar-H 3059, CH2 2950, 2832, C¼¼O of imida-
zolinone 1791, C¼¼N imidazolinone 1654, C¼¼N of pyrimidine
form): d 1.19 (t, 3H, J ¼ 7.62 Hz, ACH3), 2.34 (s, 3H,
ACH3), 2.51 (q, 2H, J ¼ 7.62 Hz, ACH2A), 3.23 (t, 2H, J ¼
6.70 Hz, ACH2), 3.80 (s, 3H, AOCH3), 4.32 (t, 2H, J ¼ 6.70
Hz, ACH2AO), 6.76–8.32 (m, 19H, pyridine, pyrimidine, and
Ar-H); 13C-NMR (CDCl3): d 15.3 (C8), 25.4 (C29), 25.7 (C7),
37.3 (C9), 56.4 (C48–C50), 67.4 (C10), 103.2 (C22), 103.8–
149.2 (C36–C41), 108.5 (C35), 114.9–158.9 (C11–C16), 123.3–
155.4 (C2–C6), 127.0–130.2 (C42–C47), 128.1–137.23 (C23–
C28), 130.2 (C32), 158.9 (C21), 160.8 (C17), 163.5 (C34), 165.5
(C19), 170.0 (C31). Anal. Calcd for C45H41N5O5: C, 73.85; H,
5.65; N, 9.57. Found: C, 73.80; H, 5.62; N, 9.51.
1615, CAOAC 1225, 1034, CACl 743 cmꢀ1 1H-NMR (deu-
;
teriochloroform): d 1.21 (t, 3H, J ¼ 7.64 Hz, ACH3), 2.55 (q,
2H, J ¼ 7.62 Hz, ACH2A), 3.25 (t, 2H, J ¼ 6.72 Hz, ACH2),
3.84 (s, 3H, AOCH3), 4.36 (t, 2H, J ¼ 6.71 Hz, ACH2AO),
6.78–8.32 (m, 18H, pyridine, pyrimidine, and Ar-H); 13C-
NMR (CDCl3): d 15.1 (C8), 25.6 (C7), 37.6 (C9), 56.4 (C48–
C50), 67.3 (C10), 103.7 (C22), 103.2–150.4 (C36–C41), 108.2
(C35), 115.0–157.2 (C11–C16), 122.1–157.4 (C2–C6), 126.6–
130.4 (C42–C47), 127.4–135.7 (C23–C28), 130.8 (C32), 160.1
(C21), 163.7 (C17), 164.5 (C34), 169.4 (C19), 170.6 (C31). Anal.
Calcd for C44H37N5O5Cl2: C, 67.18; H, 4.74; N, 8.90. Found:
C, 67.12; H, 4.71; N, 8.91.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(1-phenyl)
pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-1H-
imidazol-5(4H)-one (6g). This compound was obtained as
brown solid, yield 55%, m.p. 102–104ꢁC Rf: 0.59; IR (KBr):
Ar-H 3064, CH2 2957, 2836, C¼¼O of imidazolinone 1795,
C¼¼N imidazolinone 1655, C¼¼N of pyrimidine 1615, CAOAC
1229, 1033 cmꢀ1 1H-NMR (deuteriochloroform): d 1.24 (t,
;
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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Design and Synthesis of New Imidazolinone Derivatives as
Potential Antifungal Agents
379
3H, J ¼ 7.61 Hz, ACH3), 2.53 (q, 2H, J ¼ 7.61 Hz, ACH2A),
3.26 (t, 2H, J ¼ 6.70 Hz, ACH2), 3.82 (s, 3H, AOCH3), 4.36
(t, 2H, J ¼ 6.70 Hz, ACH2AO), 6.78–8.37 (m, 19H, pyridine,
pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.6 (C8), 25.6
(C7), 37.4 (C9), 56.3 (C48–C50), 67.6 (C10), 103.5 (C22),
103.5–150.3 (C36–C41), 108.7 (C35), 114.8–157.6 (C11–C16),
122.4–157.3 (C2–C6), 126.4–130.6 (C42–C47), 127.5–133.0
(C23–C28), 130.4 (C32), 160.1 (C21), 163.5 (C17), 164.2 (C34),
169.6 (C19), 170.1 (C31). Anal. Calcd. for C44H39N5O5: C,
73.62; H, 5.48; N, 9.76. Found: C, 73.65; H, 5.45; N, 9.75.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(4-fluoro
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6h). This compound was
obtained as brown solid, yield 52%, m.p. 125–128ꢁC, Rf: 0.60; IR
(KBr): Ar-H 3068, CH2 2955, 2832, C¼¼O of imidazolinone
1793, C¼¼N imidazolinone 1653, C¼¼N of pyrimidine 1617,
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(3,4-dichlor-
ophenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6k). This compound was
obtained as brown solid, yield 65%, m.p. 83–85ꢁC, Rf: 0.66; IR
(KBr): Ar-H 3060, CH2 2952, 2834, C¼¼O of imidazolinone
1798, C¼¼N imidazolinone 1658, C¼¼N of pyrimidine 1610,
CAOAC 1220, 1035, CACl 749 cmꢀ1; 1H-NMR (deuteriochloro-
form): d 1.22 (t, 3H, J ¼ 7.63 Hz, ACH3), 2.50 (q, 2H, J ¼ 7.63
Hz, ACH2A), 3.20 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.83 (s, 3H,
AOCH3), 4.30 (t, 2H, J ¼ 6.72 Hz, ACH2AO), 6.78–8.32 (m,
19H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.6
(C8), 25.1 (C7), 37.6 (C9), 56.4 (C48–C50), 67.8 (C10), 103.0 (C22),
103.1–150.2 (C36–C41), 108.2 (C35), 114.9–157.2 (C11–C16),
122.7–157.3 (C2–C6), 126.5–130.5 (C42–C47), 127.0–133.8 (C23–
C28), 130.5 (C32), 160.2 (C21), 163.4 (C17), 164.2 (C34), 169.4
(C19), 170.7 (C31). Anal. Calcd. for C44H37N5O5Cl2: C, 67.18; H,
4.74; N, 8.90. Found: C, 67.12; H, 4.72; N, 8.88.
1
CAOAC 1226, 1038, CAF 974 cmꢀ1; H-NMR (deuteriochloro-
form): d 1.16 (t, 3H, J ¼ 7.63 Hz, ACH3), 2.56 (q, 2H, J ¼ 7.62
Hz, ACH2A), 3.23 (t, 2H, J ¼ 6.70 Hz, ACH2), 3.81 (s, 3H,
AOCH3), 4.36 (t, 2H, J ¼ 6.70 Hz, ACH2AO), 6.78–8.32 (m,
19H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.8
(C8), 25.2 (C7), 37.5 (C9), 56.4 (C48–C50), 67.5 (C10), 103.8 (C22),
103.2–150.8 (C36–C41), 108.4 (C35), 114.9–157.5 (C11–C16),
122.4–157.2 (C2–C6), 126.1–130.3 (C42–C47), 116.0–162.9 (C23–
C28), 130.1 (C32), 160.7 (C21), 163.6 (C17), 164.4 (C34), 169.3
(C19), 170.3 (C31). Anal. Calcd. for C44H38N5O5F: C, 71.82; H,
5.21; N, 9.52. Found: C, 71.81; H, 5.23; N, 9.51.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(4-chloro-
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-
1H-imidazol-5(4H)-one (6l). This compound was obtained as
dark yellow solid, yield 67%, m.p. 115–118ꢁC, Rf: 0.54; IR
(KBr): Ar-H 3063, CH2 2951, 2834, C¼¼O of imidazolinone
1794, C¼¼N imidazolinone 1653, C¼¼N of pyrimidine 1615,
CAOAC 1227, 1035, CACl 743 cmꢀ1; 1H-NMR (deuteriochloro-
form): d 1.23 (t, 3H, J ¼ 7.64 Hz, ACH3), 2.56 (q, 2H, J ¼ 7.64
Hz, ACH2A), 3.26 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.84 (s, 3H,
AOCH3), 4.33 (t, 2H, J ¼ 6.71 Hz, ACH2AO), 6.78–8.31 (m,
19H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.4
(C8), 25.7 (C7), 37.7 (C9), 56.3 (C48–C50), 67.4 (C10), 103.4 (C22),
103.4–150.6 (C36–C41), 108.4 (C35), 114.8–157.6 (C11–C16),
122.7–157.4 (C2–C6), 126.4–130.0 (C42–C47), 128.9–134.3 (C23–
C28), 130.6 (C32), 160.2 (C21), 163.4 (C17), 164.2 (C34), 169.5
(C19), 170.6 (C31). Anal. Calcd. for C44H38N5O5Cl: C, 70.25; H,
5.09; N, 9.31. Found: C, 70.24; H, 5.02; N, 9.32.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(2,4-difluoro
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-
1H-imidazol-5(4H)-one (6i). This compound was obtained as
brown solid, yield 60%, m.p. 95–99ꢁC, Rf: 0.59; IR (KBr): Ar-H
3066, CH2 2953, 2833, C¼¼O of imidazolinone 1795, C¼¼N imi-
dazolinone 1654, C¼¼N of pyrimidine 1614, CAOAC 1225,
1
1035, CAF 975 cmꢀ1; H-NMR (deuteriochloroform): d 1.20 (t,
3H, J ¼ 7.63 Hz, ACH3), 2.55 (q, 2H, J ¼ 7.63 Hz, ACH2A),
3.25 (t, 2H, J ¼ 6.71 Hz, ACH2), 3.83 (s, 3H, AOCH3), 4.36 (t,
2H, J ¼ 6.70 Hz, ACH2AO), 6.74–8.30 (m, 18H, pyridine, py-
rimidine, and Ar-H); 13C-NMR (CDCl3): d 15.2 (C8), 25.5 (C7),
37.6 (C9), 56.3 (C48–C50), 67.6 (C10), 103.2 (C22), 103.6–150.4
(C36–C41), 108.3 (C35), 114.7–157.3 (C11–C16), 122.3–157.4 (C2–
C6), 126.4–130.6 (C42–C47), 111.6–164.5 (C23–C28), 130.6 (C32),
160.8 (C21), 163.2 (C17), 164.2 (C34), 169.3 (C19), 170.2 (C31).
Anal. Calcd. for C44H37N5O5F2: C, 70.11; H, 4.95; N, 9.29.
Found: C, 70.13; H, 4.92; N, 9.27.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(3-methoxy-
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-
1H-imidazol-5(4H)-one (6m). This compound was obtained as
yellow solid, yield 52%, m.p. 114–116ꢁC, Rf: 0.61; IR (KBr):
Ar-H 3062, CH2 2952, 2831, C¼¼O of imidazolinone 1796,
C¼¼N imidazolinone 1658, C¼¼N of pyrimidine 1617, CAOAC
1221, 1036 cmꢀ1 1H-NMR (deuteriochloroform): d 1.17 (t,
;
3H, J ¼ 7.64 Hz, ACH3), 2.53 (q, 2H, J ¼ 7.64 Hz, ACH2A),
3.26 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.81 (s, 3H, AOCH3), 4.33
(t, 2H, J ¼ 6.71 Hz, ACH2AO), 6.73–8.36 (m, 19H, pyridine,
pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.6 (C8), 25.3
(C7), 37.2 (C9), 55.8 (C29), 56.4 (C48–C50), 67.2 (C10), 103.2
(C22), 103.3–150.6 (C36–C41), 108.7 (C35), 114.2–157.5 (C11–
C16), 122.5–157.3 (C2–C6), 126.1–130.3 (C42–C47), 112.2–
161.1 (C23–C28), 130.4 (C32), 160.3 (C21), 163.2 (C17), 164.1
(C34), 169.4 (C19), 170.2 (C31). Anal. Calcd. for C45H41N5O6:
C, 72.27; H, 5.53; N, 9.36. Found: C, 72.25; H, 5.55; N, 9.34.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(3-fluoro-
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6n). This compound was
obtained as brown solid, yield 51%, m.p. 100–103ꢁC, Rf: 0.62; IR
(KBr): Ar-H 3067, CH2 2955, 2835, C¼¼O of imidazolinone
1795, C¼¼N imidazolinone 1654, C¼¼N of pyrimidine 1613,
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(4-bromo
phenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzyli-
dene)-1H-imidazol-5(4H)-one (6j). This compound was
obtained as brown solid, yield 61%, m.p. 130–132ꢁC, Rf: 0.63;
IR (KBr): Ar-H 3065, CH2 2954, 2835, C¼¼O of imidazolinone
1794, C¼¼N imidazolinone 1656, C¼¼N of pyrimidine 1612,
CAOAC 1225, 1033, CABr 864 cmꢀ1 1H-NMR (deuterio-
;
chloroform): d 1.19 (t, 3H, J ¼ 7.63 Hz, ACH3), 2.55 (q, 2H, J
¼ 7.63 Hz, ACH2A), 3.24 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.82 (s,
3H, AOCH3), 4.34 (t, 2H, J ¼ 6.72 Hz, ACH2AO), 6.78–8.36
(m, 19H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d
15.5 (C8), 25.4 (C7), 37.1 (C9), 56.4 (C48–C50), 67.4 (C10), 103.3
(C22), 103.7–150.6 (C36–C41), 108.4 (C35), 114.7–157.1 (C11–
C16), 122.5–157.8 (C2–C6), 126.4–130.6 (C42–C47), 123.1–132.1
(C23–C28), 130.5 (C32), 160.4 (C21), 163.4 (C17), 164.3 (C34),
169.5 (C19), 170.6 (C31). Anal. Calcd. for C44H38N5O5Br: C,
66.33; H, 4.81; N, 8.79. Found: C, 66.30; H, 4.80; N, 8.77.
1
CAOAC 1224, 1032, CAF 974 cmꢀ1; H-NMR (deuteriochloro-
form): d 1.19 (t, 3H, J ¼ 7.62 Hz, ACH3), 2.51 (q, 2H, J ¼ 7.61
Hz, ACH2A), 3.25 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.82 (s, 3H,
AOCH3), 4.35 (t, 2H, J ¼ 6.72 Hz, ACH2AO), 6.78–8.34 (m,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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N. B. Patel and H. R. Patel
Vol 48
19H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d 15.3
(C8), 25.6 (C7), 37.4 (C9), 56.4 (C48–C50), 67.3 (C10), 103.7 (C22),
103.3–150.6 (C36–C41), 108.3 (C35), 114.4–157.4 (C11–C16),
128.5–157.2 (C2–C6), 126.3–130.2 (C42–C47), 115.5–163.4 (C23–
C28), 130.5 (C32), 160.2 (C21), 163.5 (C17), 164.5 (C34), 169.3
(C19), 170.2 (C31). Anal. Calcd. for C44H38N5O5F: C, 71.82; H,
5.21; N, 9.52. Found: C, 71.84; H, 5.22; N, 9.51.
REFERENCES AND NOTES
[1] Desai, N. C.; Bhavsar, A. M.; Baldaniya, B. B. Indian J Pharm
Sci 2009, 71, 90.
[2] Solankee, A.; Solankee, S.; Patel, G. Rasayan J Chem 2008,
1, 228.
[3] El-Sayed Ali, T.; Abdel-Aghfaar Abdel-Aziz, S.; Metwali
El-Shaaer, H.; Ismail Hanafy, F.; Zaky El-Fauomy, A. Turk J Chem
2008, 32, 365.
1-(4-{4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl}-6-(3,4-difluor-
ophenyl)pyrimidin-2-yl)-2-phenyl-4-(3,4,5-trimethoxybenzylidene)-
1H-imidazol-5(4H)-one (6o). This compound was obtained as
brown solid, yield 62%, m.p. 180–182ꢁC, Rf: 0.60; IR (KBr):
Ar-H 3063, CH2 2957, 2836, C¼¼O of imidazolinone 1796,
C¼¼N imidazolinone 1652, C¼¼N of pyrimidine 1612, CAOAC
[4] Mistry, R. N.; Desai, K. R. E-J Chem 2005, 2, 42.
[5] Benkli, K.; Karaburun, A. C.; Gundo Du-Karaburun, N.;
Demirayak, S.; Guven, K. Arch Pharm Res 2003, 26, 773.
[6] De, B.; Gupta, J.; Saravanan, V. S. Acta Pharm 2005, 55,
287.
1224, 1037, CAF 972 cmꢀ1 1H-NMR (deuteriochloroform): d
;
[7] Amir, M.; Kumar, A.; Ali, I.; Khan, S. A. Indian J Chem B
2009, 48, 1288.
1.21 (t, 3H, J ¼ 7.63 Hz, ACH3), 2.54 (q, 2H, J ¼ 7.62 Hz,
ACH2A), 3.21 (t, 2H, J ¼ 6.72 Hz, ACH2), 3.81 (s, 3H,
AOCH3), 4.36 (t, 2H, J ¼ 6.72 Hz, ACH2AO), 6.78–8.40 (m,
18H, pyridine, pyrimidine, and Ar-H); 13C-NMR (CDCl3): d
15.5 (C8), 25.8 (C7), 37.8 (C9), 56.3 (C48–C50), 67.4 (C10), 103.8
(C22), 103.4–150.6 (C36–C41), 108.3 (C35), 114.7–157.4 (C11–
C16), 122.3–157.3 (C2–C6), 126.3–130.2 (C42–C47), 117.5–149.5
(C23–C28), 130.4 (C32), 160.7 (C21), 163.6 (C17), 164.3 (C34),
169.4 (C19), 170.6 (C31). Anal. Calcd. for C44H37N5O5F2: C,
70.11; H, 4.95; N, 9.29. Found: C, 70.09; H, 4.94; N, 9.27.
[8] Ding, M.; Zeng, G.; Liu, Z. Phosphorus Sulfur Silicon
2002, 177, 1315.
[9] Huang, X.; Liu, Z.; Yang, F.; Ding, M. Phosphorus Sulfur
Silicon 2007, 182, 939.
[10] Demirayak, S.; Karaburun, A. C.; Kayagil, I.; Erol, K.; Sir-
magul, B. Arch Pharm Res 2004, 27, 13.
[11] Joshi, H.; Upadhyay, P.; Karia, D.; Baxi, A. J. Eur J Med
Chem 2003, 38, 837.
[12] Xue, N.; Yang, X.; Wu, R.; Chen, J.; He, Q.; Yang, B.; Lu,
X.; Hu, Y. Bioorg Med Chem 2008, 16, 2550.
[13] Patel, N. B.; Patel, H. R. Arkivoc 2009, 12, 302.
[14] Patel, N. B.; Patel, H. R. Int J Drug Design Discov 2010, 1,
93.
Acknowledgments. The authors thank the Professor and Head
of the Department of Chemistry at the Veer Narmad South
Gujarat University for laboratory facilities; the Librarian of the
Veer Narmad South Gujarat University, Surat, for library facili-
ties; and Dhanji Rajani, Microcare Laboratory, Surat, for antimi-
crobial activity. The authors also thank the Central Drug
Research Institute, Lucknow, for elemental analyses, and the
Sophisticated Analytical Instrumentation Facility, Chandigarh,
for IR, 1H-NMR, and 13C-NMR spectral analyses.
[15] Rattan, A. Antimicrobials in Laboratory Medicine; Church-
ill BI, Livingstone: New Delhi, 2000; p 85.
[16] Gaonkar, S. L.; Rai, K. M. L.; Prabhuswamy, B. Eur J Med
Chem 2006, 41, 841.
[17] Momose, Y.; Meguro, K.; Ikeda, H.; Hatanaka, C.; Satoru,
O. I.; Sohda, T. Chem Pharm Bull 1991, 396, 1440.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet