Dimeric 2-(2-chlorophenyl)-quinazolin-4-ones as potential antimicrobial agents

Article abstract of DOI:10.1007/s00044-011-9621-5

3-(Aryl)-2-(2-chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3- hydroquinazolin-3yl)]ethyl}-3-hydroquinazolin-4-ones had been selected as target bio-active molecules. Several quinazoline derivatives were prepared by using anthranilic acid, acid chloride, 2-

Full text of DOI:10.1007/s00044-011-9621-5

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2012) 21:1127–1135
DOI 10.1007/s00044-011-9621-5
ORIGINAL RESEARCH
Dimeric 2-(2-chlorophenyl)-quinazolin-4-ones as potential
antimicrobial agents
•
•
•
N. C. Desai Amit Dodiya Nayan Bhatt
Mukesh Kumar
Received: 13 December 2010 / Accepted: 5 March 2011 / Published online: 27 March 2011
Ó Springer Science+Business Media, LLC 2011
Abstract 3-(Aryl)-2-(2-chlorophenyl)-6-{2-[2-(2-chlo-
rophenyl)-4-oxo(3-hydroquinazolin-3yl)]ethyl}-3-hydro-
quinazolin-4-ones had been selected as target bio-active
molecules. Several quinazoline derivatives were prepared
by using anthranilic acid, acid chloride, 2-amino-ethanol,
and different amines. Newly synthesized compounds were
screened for their antibacterial and antifungal activities on
Escherichia coli, Staphylococcus aureus, Pseudomonas
aeruginosa, Staphylococcus pyogenes, Candida albicans,
Aspergillus niger, and Aspergillus clavatus. The com-
pounds 5e, 5g, and 5h are shown to have excellent activity,
while 5c, 5d, 5i, 5k, 5l are shown to have very good
activity against several strains of bacteria. The structures of
the synthesized compounds were firmly established by
well-defined spectral analysis techniques like IR, 1H-NMR,
13C-NMR, and Mass spectra.
the development of novel antimicrobials (Dahiya and Kumar,
2008). Quinazolines are heterocyclic compounds having
wide spectrum medicinal values such as antihypertensive
(Pandey and Bajpai, 2004), antiviral (Hess and Cronin, 1968)
anti-inflammatory (Yadav and Shirude, 2006; Wand and Xia,
2003). The diverse pharmacological properties exhibited by
quinazolones have been of much significance in recent years.
2,3-Disubstituted quinazolones have beendemonstrated to be
associated with antiviral (Pandey et al., 1988) and antifungal
activities (Tiwari et al., 2006). In addition, some quinazolone
derivatives containing sulphonamido group caused antihy-
pertensive effect probably dueto the initialreductionof blood
volume because of Na? depletion and subsequently on
account of direct relaxation of arteriolar smooth muscle
(Papsech and Schroeder, 1956). Some compounds were
generallyeffectiveinlowerbloodpressureinthespontaneous
hypertensive rats model and showed a-adrenergic blocking
activity (Atkins and Nicolosi, 1979).
Keywords Quinazolinone Á
Antimicrobial activity of quinazolinone moiety Á
Dimeric quinazolinone
Looking to the medicinal importance of these com-
pounds, this study is aimed to synthesize new bio-active
molecules and screen them for antimicrobial activity (De-
sai and Moradia, 2007; Desai and Shah, 2001; Desai and
Bhatt, 1995; Desai and Desai, 2005). The study reported in
this article is in continuation of the previous work aimed at
synthesizing bio-active heterocyclic entities (Desai and
Desai, 2005; Desai and Undavia, 1998; Desai and Undavia,
1996; Desai and Bhavsar, 2008; Desai and Saxena, 2008;
Desai and Baldaniya, 2009).
Introduction
Since the last half of the 20th century, bacteria have
developed resistance against currently available drugs and
therefore it is an ongoing effort, for medicinal chemists to
synthesize new chemotherapeutic agents. In continuation to
this, compounds bearing heterocyclic nuclei have received
much attention because of their chemotherapeutic value in
Nanda and his co-workers synthesized 3-(arylidenea-
mino)-2-phenylquinazoline-4(3H)-ones, which were inves-
tigated for their antimicrobial activity against both gram
positive (Staphylococcus aureus 6571 and Bacillus subtilis)
and gram negative bacteria (Escherichia coli K12 and
Shigella dysenteriae 6) using a turbidometric assay
method. It was found that the incorporation of the
N. C. Desai (&) Á A. Dodiya Á N. Bhatt Á M. Kumar
Medicinal Chemistry Division, Department of Chemistry,
Bhavnagar University, Bhavnagar 364 002, India
e-mail: dnisheeth@rediffmail.com
123

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Med Chem Res (2012) 21:1127–1135
3-arylideneamino substituent enhanced the antibacterial
activity of the quinazolone system (Nanda et al., 2007). On
the basis of this, for the first time the authors have reported
the dimeric quinazolinones and try to evaluate antimicro-
bial activity. Results of the antimicrobial activity clearly
indicate that by introducing the dimeric structure of qui-
nazoline, the activity was enhanced. It was report herein
the synthesis of quinazolinones with a view to synthesize
more potentially bio-active molecules.
downfield, e.g., the C-2 and C-14 carbonyl, which are
directly linked to the ring nitrogen, have a chemical shift
value of d = 161.4 and 160.8 ppm, whereas the C-24 and
C-30 are linked to one chlorine atom appears at the same
d = 130.8 ppm. The carbons C-1 and C-15 which are
attached onbothsidesof nitrogenatoms appeared at the same
high value of d = 164.0 ppm, The chemical shift of the ring
carbons at C-3 and C-13 are affected by the presence of the
nearest carbonyl group and appeared at the same d =
120.8 ppm. The C-36 appeared at d = 142.7 ppm due to the
strong electron withdrawing influence of nitro group. The
methyl group attached to C-34 appeared at d = 134.9 ppm
while the carbon of the methyl group C-37 appears at low
value of d = 23.3 ppm. The C-34 which is attached to
methyl group appeared at d = 125.7 ppm. The C-35 which
is affected by the influence of the C-36 which is attached to
nitro group and C-34 at methyl group appeared at
d = 125.7 ppm. C-8 and C-16 which are present in the
quinazolinone rings appeared at d = 151.2 and 148.4 ppm
due to the nitrogen atmosphere on the nearest carbon atom.
The carbon C-32 appeared at d = 122.4 ppm while the
carbons C-19 and C-25 of the chloro benzene rings which are
directly attached to quinazolinone rings appeared at the same
value of d = 123.0 ppm. The carbons of the phenyl rings of
quinazolinone nucleus appeared between d = 122.4 to
133.5 ppm, respectively. The carbons of the chloro benzene
ring which are attached to the quinazolinone ring having
equivalent carbons C-20 and C-26 appeared at d =
127.5 ppm. C-21 and C-27 appeared at d = 127.0, C-22 and
C-28 appeared at d = 131.6 ppm, C-23 and C-29 appeared
at 128.9, respectively. The carbon skeleton of compound-5g
is described in Fig. 1.
This study is in conjunction with the ongoing pro-
gramme of utilizing readily obtainable starting materials
for the synthesis of heterocyclic systems (Madkour, 2002;
Madkour et al., 2001; Mahmoud and Madkour, 2001;
Salem et al., 2001; Madkour et al., 1998; Madkour et al.,
1994 Madkour, 1993).
One of the most important features of (4H)-3,1-ben-
zoxazinone chemistry is their use as key starting materials
for further transformations. They are indeed useful inter-
mediates in organic synthesis affording through reaction
with nitrogen nucleophiles 4(3H)quinazolinones. This scaf-
fold (5) is a part of the synthesis of new chemical entities in
the form of antimicrobial agents. 3-(Aryl)-2-(2-chloro-
phenyl)-6-{2-[2-chlorophenyl)-4-oxo(3-hydro-quinazolin-
3yl)]ethyl}hydroquinazolin-4-ones (5a–l) were synthe-
sized in five steps. First step involves condensation of
2-amino benzoic acid with 2-chlorobenzoyl chloride to
give 2-(2-chlorophenyl)benzo[d]1,3-oxazin-4-one (1). It
was condensed with 2-amino ethyl alcohol to yield 2-(2-
chlorophenyl)-3-(2-hydroxyethyl)-3-hydroquinazolin-4-one
(2). Compound (2) was further condensed with 2-amino
benzoic acid to give 2-amino-5-{2-[2-chlorophenyl)-4-
oxo(3-hydroquinazolin-3-yl)ethyl} benzoic acid (3), which
on further treatment with 2-chloro benzoyl chloride fur-
nished 2-(2-chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo-
(3-hydroquinazolin-3-yl)]ethyl}benzo[d]1,3-oxozin-4-one
(4). Finally, compound (4) on treatment with different
aromatic amines yielded 2-(2-chlorophenyl)-5-{2-[2-(2-
chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]ethyl}-3-aryl-
3-hydroquinazolin-4-ones (5a–l).
Antimicrobial activity
For antibacterial activity, compounds 5b, 5d, 5i, 5k, and 5l
(R = 2-Cl-C6H4, 2,4-(CH3)2-C6H3, 3-NO2-C6H4, 3,4-
(Cl)2-C6H3 and 2,6-(Cl)2-4-NO2-C6H2) are considered to
37
CH
34
3
35
Results and discussion
36
NO
O
2
33
5
4
The characterization of newly synthesized compounds of
the series was carried out by IR, NMR, and Mass spectra
and the data is discussed in the Experimental section.
O
2
32
26
31
3
14
27
6
N
13
12
18
9
N
7
28
8
15
25
Cl
11
13C-NMR—Data
1
10
N
N
16
29
19
30
20
17
21
22
Fig. 1 Carbon skeleton of the compound-5g
The final compound-5g has dimeric quinazolinone rings.
The chemical shifts of the final compound carbons vary from
d = 164.0 to 23.3 ppm. The carbon nuclei under the influ-
ence of a strong electronegative environment appears
Cl
24
23
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Med Chem Res (2012) 21:1127–1135
1129
be very good active against S. pyogenes as compared to the
standard drug ampicillin, while compounds 5c, 5f, and 5j
(R = 2,3-(CH3)2-C6H3, 4-OCH3-2-NO2-C6H3, and 4-NO2-
C6H4) are considered as good active against S. pyogenes,
while compounds 5e (R = 2,5-(CH3)2-C6H3 and 5g
(R = 4-CH3-2-NO2-C6H3) are considered as excellent
active against S. pyogenes and compound-5h considered as
very excellent against S. pyogenes as compared to the
standard drug ampicillin. Compounds 5b, 5e, 5f, 5g, 5h, 5j,
and 5l (R = 2-Cl-C6H4, 2,5-(CH3)2-C6H3, -4-OCH3-2-NO2-
C6H3, 4-CH3-2-NO2-C6H3, 2-NO2-C6H4, 4-NO2-C6H4, and
2,6-(Cl)2-4-NO2-C6H2) are considered as good active
against gram positive bacteria S. aureus, while 5d, 5i, and
5k (R = 2,4-(CH3)2-C6H3, 3-NO2-C6H4, 3,4-(Cl)2-C6H3)
are considered as very good active against S. aureus as
compared to the standard drug ampicillin. Compounds 5c,
5d, 5i, and 5k (2,3(CH3)2-C6H3, 2,4-(CH3)2-C6H3, 3-NO2-
C6H4, and 3,4-(Cl)2-C6H3) are considered as good active
against gram negative P.aeruginosa bacteria as compared
to the standard drug ampicillin, while compounds 5a, 5e,
and 5h (R = 4-Br-C6H4, 2,5-(CH3)2-C6H3 and 2-NO2-
C6H4) are considered as moderately active as compared to
the standard drug ampicillin. Compounds 5e, 5f, 5h, and
5j (R = 2,5(CH3)2-C6H3, 4-OCH3-2-NO2-C6H3, 2-NO2-
C6H4, and 4-NO2-C6H4) are considered good active against
gram negative bacteria as compared to the standard drug
ampicillin, while the compounds 5c, 5d, and 5i (R = 2,3-
(CH3)2-C6H3, 2,4(CH3)2-C6H3, and 3-NO2-C6H4) are
considered as very good active against E. coli, while
compounds 5a, 5g, and 5k (4-Br-C6H4,4-CH3-2-NO2-C6H3
and 3,4-(Cl)2-C6H3) are considered as moderately active
against E.coli as compared to the standard drug ampicillin.
The antibacterial activity of the compounds was enhanced
due to the introduction of nitro, chloro, and methyl groups
in the dimeric structure of quinazolinone. The results of
antibacterial studies are given in Table 1. For antifungal
activity, it has been observed that compounds 5d, 5f, 5h,
and 5k (R = 2,4(CH3)2-C6H3, 4-OCH3-2-NO2-C6H3,
2-NO2-C6H4, 3,4-(Cl)2-C6H3) are found to be excellent
active against C. albicans, compound 5e (R = 2,5-(CH3)2-
C6H3) is considered as very good active against C. albicans
as compared to the standard drug griseofulvin, while com-
pounds 5b, 5c, 5g, and 5j (R = 2-Cl-C6H4, 2,3-(CH3)2-
C6H3), 4-CH3-2-NO2-C6H3, 4-NO2-C6H4) are considered
as good active against C.albicans. Compounds 5b, 5h, and
5l (R = 2-Cl-C6H4, 2-NO2-C6H4, and 2,6-(Cl)2-4-NO2-
C6H2) are considered as good active against A.niger as
compared to the standard drug griseofulvin. Compounds
Table 1 Results of antibacterial and antifungal screening of the compounds (5a–l)
S.
no.
–Ar
Minimum inhibitory concentration (MIC) ug/ml SD
Minimum inhibitory concentration (MIC)
in ug/ml SD
E. coli P. aeruginosa
MTCC 443 MTCC 1688
S. aureus
MTCC 96
S. pyogenes
MTCC 442
C. albicans
MTCC 227
A. niger
MTCC 282
A. clavatus
MTCC 1323
5a -4-Br-C6H4
5b -2-C1-C6H4
200 4.50* 200 3.78*
500 4.72* 500 3.05*
50 4.93* 100 4.04*
500 4.04* 500 4.04*
200 3.05* 50 2.51*
500 4.04* 100 4.50*
1000 2.51*
500 4.04*
500 4*
500 4.50* 1000 3.05*
100 3.51* 100 4*
500 4.35* 500 3.78*
5c -2,3-(CH3)2-
C6H3
5d -2,4-(CH3)2-
C6H3
50 34.04* 100 4.58*
100 3.78* 200 4*
100 4.04* 500 3.46*
50 3.78*
50 4*
100 4.58*
200 4.04*
100 4.50*
500 2.30*
500 3.60* 500 3.05*
500 4.50* 500 3.60*
500 4.58* 500 4.04*
1000 4.04* 100 4.04*
5e -2,5-(CH3)2-
C6H3
100 3.05* 25 1*
100 2.51* 100 3.51*
100 3.51* 25 1*
200 4.04* 12.5 1.32*
5f -4-OCH3-2-
NO2-C6H3
5g -4-CH3-2-NO2- 200 4.93* 500 4.58*
C6H3
5h -2-NO2-C6H4
5i -3-NO2-C6H4
100 4*
200 3.60*
100 3.21*
1000 3.51*
500 3.46*
100 3.78*
100 3.05* 1000 4.16*
1000 3.51* 100 3*
50 3.78* 100 4.04*
100 3.21* 500 3.51*
200 3.21* 100 3.05*
50 3*
200 3.21* 100 4.16*
50 3.51* 50 2.08*
50 4.04*
5j -4-NO2-C6H4
500 3.51* 500 4.04*
500 4.16* 100 3.05*
5k -3,4-(C1)2-
C6H3
51 -2,6-(C1)2-4-
NO2-C6H2
500 4.58* 500 3.51*
100 2.0* 100 1.0*
100 3.05* 50 3.60*
250 1.52* 100 2.08*
500 3.05*
100 4*
100 2.51*
Ampicillin
–
–
–
Griseofulvin
–
–
–
–
500 0.57*
100 1*
100 1.15*
SD Standard deviation * P B 0.0001
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Med Chem Res (2012) 21:1127–1135
5b, 5g, 5i, 5k, and 5l (R = 2-Cl-C6H4, 4-CH3-2-NO2-
C6H3, 3-NO2-C6H4, 3,4-(Cl)2-C6H3, 2,6-(Cl)2-4-NO2-
C6H2) are considered as good active against A. clavatus as
compared to the standard drug griseofulvin. The enhance-
ment of the activity of these compounds is due to the
presence of nitro and chloro groups in the dimeric structure
of quinazolinone.
FT–IR spectrophotometer. 1H-NMR and 13C-NMR
spectra were recorded on Bruker DPX-40C instrument
at 400 MHz. Chemical shifts are reported in ppm in
reference to the residual solvent signal. Mass spectra
were recorded on JEOL SX-102. Elemental analysis
was performed by Perkin-Elmer 2400-CHN analyzer.
Melting points were recorded on Gallenkamp apparatus
and were uncorrected. Aluminum-coated TLC plates 60
F245 (E. Merck) were used for monitoring of reaction
and purity of compounds. In the conventional method,
compounds were synthesized by using Random syn-
thesizer. Bookie Rotavapour is used for distillation
Scheme 1.
Materials and methods
All the required chemicals were purchased from E.
Merck. IR spectra were recorded on Perkin Elmer
Scheme 1 Preparation of the
compounds 5a–l
COOH
O
COCl
Cl
Pyridine
0-5°C
O
+
N
NH
2
Cl
H N CH -CH -OH
2
2
2
Reflux
1
COOH
NH
2
O
N
O
N
OH
N
N
Anthranilic acid
Ethanol / Con.HCl
Reflux
2
3
Cl
Cl
COCl
Pyridine
0-5°C
Cl
O
O
N
Cl
O
N
Ar
N
Ar-NH
2
N
Pyridine Reflux
O
4
Cl
N
Cl
O
N
N
5a-l
Cl
Ar = different substituents
123

Med Chem Res (2012) 21:1127–1135
Antibacterial activity
1131
method, it has been observed that the differences below
0.0001 level (P B 0.0001) were considered as statistically
significant.
The newly synthesized compounds were screened for their
antibacterial activity against gram positive bacteria
Staphylococcus aureus (MTCC-96) and Streptococcus py-
ogenes (MTCC-442) and gram negative Escherichia coli
(MTCC-443) and Pseudomonas aeruginosa (MTCC-1688).
Antibacterial activity was carried out by serial broth dilu-
tion method (Ghalem and Mohamed, 2009; Desai and
Trivedi, 1993; Al-Bayati and Al-Mola, 2008). The standard
strains used for the antimicrobial activity was procured
from Institute of Microbial Technology, Chandigarh. The
compounds (5a–l) were screened for their antibacterial
activity in triplicate against Escherichia coli, Staphylo-
coccus aureus, Pseudomonas aeruginosa, and Streptococ-
cus pyogenes at different concentrations of 1000, 500, 200,
100, 50, 25, 12.5 lg/ml as shown in (Table 1). The drugs
which were found to be active in primary screening were
similarly diluted to obtain 100, 50, 25, 12.5 lg/ml con-
centrations. 10 lg/ml suspensions were further inoculated
on appropriate media and growth was noted after 24 and
48 h. The lowest concentration, which showed no growth
after spot subculture was considered as MIC for each drug.
The highest dilution showing at least 99% inhibition is
taken as (MIC). The test mixture should contain 108 cells/
ml. The standard drug used in this study was ‘ampicillin’
for evaluating antibacterial activity which showed (0.25,
0.05, 0.5, and 1 lg/ml) MIC against E. coli, P. aeruginosa,
S. aureus, and S. pyogenes, respectively.
Experimental
Preparation of 2-(2-chlorophenyl) benzo[d]1,3-oxazin-4-
one (1) was synthesized according to the reported method
(Desai NC and Undavia NK, 1996).
Preparation of 2-(2-chlorophenyl)-3-(2-hydroxyethyl)-
3-hydroquinazolin-4-one (2)
2-Amino ethyl alcohol (0.02 mol) and compound (1)
(0.01 mol) was refluxed for 4 h. The solution was poured
into ice-cold water and then required amount of dilute
hydrochloric acid (10%) was added to remove unreacted
2-amino ethyl alcohol. The solid product was filtered and
washed with cold water. The resulting solid was recrys-
tallized from ethanol (99%). m.p.: 178°C, yield: 65%; IR
(KBr): 3335 cm-1 (O–H str.), 3110, 3065 (C–H str., aro-
matic ring), 2835 (C–H str., –CH2 group), 1735(C=O str.,
amide group), 1652, 1615 (C=N, C=C str., quinazoline
ring), 820 (C–Cl stretching); 1H NMR (CDCl3) : 6.79–7.85
(m, 8H, Ar–H), 3.20 (t, 2H, O–CH2), 3.45 (t, 2H, N–CH2);
4.2 (s, 1H, -OH); 13C-NMR (d Value): 41.5, 58.9, 120.8,
122.4, 123.0, 127.0, 127.4, 127.5, 128.8, 128.9, 130.8,
131.6, 133.5, 151.2, 161.4, 164.0; GCMS : m/z : 300.07
(M?); Anal. Calc. for C16H13ClN2O2: C-63.90%, H-4.36%,
N-9.32%. Found: C-63.25%, H-4.24%, N-9.84%.
Antifungal activity
Same compounds were tested for antifungal activity in
triplicate against Candida albicans, Aspergillus nigerm, and
Aspergillus clavatus at various concentrations of 1000, 500,
200, and 100 lg/ml as shown in (Table 1). The results were
recorded in the form of primary and secondary screening.
The synthesized compounds were diluted at 1000 lg/ml
concentration, as a stock solution. The synthesized com-
pounds which were found to be active in this primary
screening were further tested in a second set of dilution
against all microorganisms. The lowest concentration,
which showed no growth after spot subculture was consid-
ered as (MIC) for each drug. The highest dilution showing at
least 99% inhibition is taken as MIC. The test mixture should
contain 108 spores/ml. MIC ‘griseofulvin’ was used as a
standard drug for antifungal activity, which showed 100 lg/
ml MIC against all fungi used for the antifungal activity.
Preparation of 2-amino-5-{2-[2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)] ethyl} benzoic acid (3)
A mixture of compound (2) (0.01 mol) and anthranilic acid
(0.01 mol) in ethanol (50 ml) containing 2 ml of concen-
trated hydrochloric acid was heated under reflux for 10 h.
Ethanol was distilled off. It was air dried and recrystallized
from ethanol (99%). m.p.: 210°C, yield: 65%; IR (KBr):
3120, 3079 (C–H str., aromatic ring), 2835 (C–H str., -CH2
group), 1705 (C=O str., acid group), 1740 (C=O str.,
amide group), 1655, 1606 (C=N, C=C, quinazoline ring),
1358(C–N str., quinazoline ring), 825(C–Cl stretching); 1H
NMR (CDCl3): 11.21 (s, 1H, –COOH), 8.5 (s, 2H, –NH2),
6.69–7.60 (m, 11H, Ar–H). 2.70 (t, 2H, C–CH2), 3.39 (t,
2H, N–CH2); 13C-NMR (d Value): 33.5, 43.1, 110.1, 116.1,
120.8, 122.4, 123.0, 127.0, 127.4, 127.5, 128.8, 128.9,
129.3, 130.0, 130.8, 131.6, 133.5, 133.7, 148.4, 151.2,
161.4, 164.0, 169.3; GCMS: m/z: 419.10 (M?); Anal. Calc.
for C23H18ClN3O3: C-65.79%, H-4.32%, N-10.01%.
Found: C-65.56%, H-4.45%, N-10.08%.
Statistical analysis
The standard deviation value is expressed in terms of SD.
On the basis of the calculated value by using ANOVA
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Med Chem Res (2012) 21:1127–1135
Preparation of 2-(2-chlorophenyl)-6-{2-[2-(2-
chlorophenyl)-4-oxo (3-hydroquinazolin-3-yl)] ethyl}
benzo[d]1,3-oxazin-4-one (4)
123.0, 123.8, 127.0, 127.4, 127.5, 127.7, 128.8, 128.9,
130.8, 131.6, 131.7, 131.8, 132.4, 133.5, 138.0, 148.4,
151.2, 160.8, 161.4, 164.0; GCMS: m/z: 694.91 (100.0%).
Anal. Calc. For C36H23BrCl2N4O2: C-62.30%, H-3.39%,
N-8.11%. Found: C-62.26%, H-3.33%, N-8.06%.
Compound (3) (0.02 mol) was dissolved in pyridine
(50 ml) by stirring slowly at room temperature. The solu-
tion was cooled to 0°C and 2-chlorobenzoyl chloride
(0.01 mol) was slowly added dropwise to this solution with
constant stirring. When the addition was completed, the
reaction mixture was further stirred for 1 h at room tem-
perature and set aside for 1 h. The pasty mass so obtained
was diluted with water (50 ml) and treated with 5% sodium
bicarbonate solution (50 ml) to remove any unreacted acid.
When the effervescence ceased, it was filtered and washed
with water to remove the adhered pyridine and the inor-
ganic materials. The crude product was dried and recrys-
tallized from ethanol. m.p.: 222°C, yield: 70%; IR (KBr):
3095, 3065(C–H str., aromatic ring), 2835(C–H str., –CH2
group), 1716, 1730 (C=O str., amide group), 1655, 1606
(C=N, C=C, quinazoline ring), 1358(C–N str., quinazoline
Physical constants and characterization of 2,3-bis(2-
chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)]ethyl}-3-hydroquinazolin-4-one
(5b)
m.p.:174°C; yield: 58%; IR (KBr): 3092, 3072 (C–H str.,
aromatic ring), 2831 (C–H str., –CH2 group), 1714, 1738
(C=O str., amide group), 1651, 1611, (C=N, C=C, qui-
nazoline ring), 1354 (C–N str., quinazoline ring), 1524 (N–
1
O str., –NO2 group), 832, 826 (C–Cl stretching); H NMR
(CDCl3): 6.52–7.90 (m, 19H, Ar–H). 2.63 (t, 2H, C–CH2),
3.37 (t, 2H, N–CH2); 13C-NMR (CDCl3): 33.1, 43.1, 120.7,
120.8, 122.3, 122.4, 123.0, 125.8, 127.0, 127.1, 127.4,
127.5, 127.7, 128.8, 128.9, 129.0, 130.5, 130.8, 131.6,
132.4, 133.5, 135.7, 138.0, 148.2, 151.2,160.6, 161.4,
164.2; GCMS: m/z: 649.96 (100.0%) (M?); Anal. Calc. For
C36H23Cl3N4O2: C-66.35%, H-3.22%, N-8.26%. Found:
C-62.30%, H-3.16%, N-8.20%.
1
ring), 822(C–Cl stretching); H NMR (CDCl3): 6.62–7.88
(m, 15H, Ar–H). 2.61 (t, 2H, C–CH2), 3.39(t, 2H, N–CH2);
13C-NMR (d Value): 33.5, 43.1, 116.2, 120.8, 122.4, 123.0,
127.0, 127.4, 127.5, 128.8, 128.9, 130.5, 130.6, 130.8,
131.6, 132.5, 133.9, 134.2, 137.8, 151.2, 156.0, 159.4,
161.4, 164.0; GCMS: m/z: 540.40 (M?); Anal. Calc. for
C30H19Cl2N3O3: C-66.67%, H-3.54%, N-7.77%. Found:
C-66.69%, H-3.55%, N-7.82%.
Physical constants and characterization of 3-(2,3-
dimethylphenyl)-2-(2-chlorophenyl)-6-{2-[2-(2-
chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]ethyl}-3-
hydroquinazolin-4-one (5c)
General preparation of 2-(2-chlorophenyl)-6-{2-[2-(2-
chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]ethyl}-3-
(aryl)-3-hydroquinazolin-4-ones (5a–l)
m.p.:197°C; yield: 56%; IR (KBr): 3085, 3068 (C–H str.,
aromatic ring), 2837 (C–H str., –CH2 group), 1718, 1734
(C=O str., amide group), 1658, 1609, (C=N, C=C, qui-
nazoline ring), 1354 (C–N str., quinazoline ring), 1522 (N–
O str., –NO2 group), 836 (C–Cl stretching); 1H NMR
(CDCl3): 6.65–7.88 (m, 18H, Ar–H). 2.65 (t, 2H, C–CH2),
3.39 (t, 2H, N–CH2), 2.37 (s, 3H, Ar–CH3), 2.33 (s, 3H,
Ar–CH3); 13C-NMR (CDCl3): 16.7, 21.8, 33.1, 43.1, 118.4,
120.7, 120.8, 122.3, 122.4, 123.0, 124.5, 125.9, 127.0,
127.4, 127.5, 127.7, 128.0, 128.8, 128.9, 130.8, 131.6,
132.4, 133.5, 135.4, 137.0, 138.0, 148.3, 151.2, 160.8,
161.1, 164.2; GCMS: m/z: 643.57 (100.0%) (M?); Anal.
Calc. For C38H28Cl2N4O2: C-70.92%, H-4.38%, N-8.70%.
Found: C-62.30%, H-3.16%, N-8.20%.
Compound (4) (0.01 mol) was taken in pyridine (30 ml)
and substituted amine (0.01 mol) was added. The reaction
mixture was refluxed for 5–6 h. The solution was poured
onto crushed ice and few drops of concentrated hydro-
chloric acid was added. The product was filtered, washed
with cold water, dried, and recrystallized from ethanol.
Physical constants and characterization of 3-(4-
bromophenyl)-2-(2-chlorophenyl)-6-{2-[2-(2-
chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]ethyl}-3-
hydroquinazolin-4-one (5a)
m.p.:176°C; yield: 75%; IR (KBr): 3095, 3065 (C–H str.,
aromatic ring), 2835 (C–H str., –CH2 group), 1716, 1730
(C=O str., amide group), 1655, 1606, (C=N, C=C, qui-
nazoline ring), 1358(C–N str., quinazoline ring), 1520 (N–
O str., –NO2 group), 832 (C–Cl stretching) 575 (C–Br
stretching); 1H NMR (CDCl3): 6.91–7.85 (m, 19H, Ar–H).
2.61 (t, 2H, C–CH2), 3.39 (t, 2H, N–CH2); 13C-NMR
(CDCl3) : 33.1, 43.1, 118.7, 120.7, 120.8, 122.3, 122.4,
Physical constants and characterization of 3-(2,4-
dimethylphenyl)-2-(2-chlorophenyl)-6-{2-[2-(2-
chlorophenyl)-4-oxo (3-hydroquinazolin-3-yl)]ethyl}-
3-hydroquinazolin-4-one (5d)
m.p.:210°C; yield: 62%; IR (KBr): 3094, 3068 (C–H str.,
aromatic ring), 2833 (C–H str., –CH2 group), 1717, 1731
123

Med Chem Res (2012) 21:1127–1135
1133
Physical constants and characterization of 2-(2-
chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)]ethyl}-3-(4-methyl-2-
nitrophenyl)-3-hydroquinazolin-4-one (5g)
(C=O str., amide group), 1656, 1607, (C=N, C=C, qui-
nazoline ring), 1359 (C–N str., quinazoline ring), 1521 (N–
O str., –NO2 group), 828 (C–Cl stretching); 1H NMR
(CDCl3): 6.52–7.85 (m, 18H, Ar–H). 2.61 (t, 2H, C–CH2),
3.30 (t, 2H, N–CH2), 2.33 (s, 3H, Ar–CH3), 2.28 (s, 3H,
Ar–CH3); GCMS: m/z: 643.57 (100.0%) (M?); 13C-NMR
(CDCl3): 19.5, 24.6, 33.1, 43.1, 120.7, 120.8, 121.4, 122.3,
122.4, 123.0, 126.2, 127.0, 127.4, 127.5, 127.7, 128.8,
128.9, 130.8, 131.1, 131.6, 132.4, 133.5, 133.9, 134.2,
138.0, 148.5, 151.2, 160.8, 161.3, 164.3; Anal. Calc. For
C38H28Cl2N4O2: C-70.92%, H-4.38%, N-8.70%. Found:
C-62.30%, H-3.16%, N-8.20%.
m.p.:220°C; yield: 55%; IR (KBr): 3082, 3061 (C–H str.,
aromatic ring), 2838 (C–H str., –CH2 group), 1719, 1738
(C=O str., amide group), 1653, 1608, (C=N, C=C, qui-
nazoline ring), 1353 (C–N str., quinazoline ring), 1520 (N–
O str., –NO2 group), 830 (C–Cl stretching); 1H NMR
(CDCl3): 6.71–7.89 (m, 18H, Ar–H). 2.61 (t, 2H, C–CH2),
3.39 (t, 2H, N–CH2), 2.25 (s, 3H, Ar–CH3); GCMS: m/z:
674.54 (100.0%) (M?); 13C-NMR (CDCl3): 23.3, 33.1,
43.1, 120.7, 120.8, 122.3, 122.4, 123.0, 125.7, 127.0,
127.4, 127.5, 127.7, 128.8, 128.9, 130.3, 130.8, 131.6,
132.4, 133.5, 134.9, 135.3, 138.0, 142.3, 148.2, 151.2,
160.6, 161.3, 164.1; Anal. Calc. For C37H25BrCl2N5O4:
C-65.88%, H-3.73%, N-10.38%. Found: C-62.30%,
H-3.16%, N-8.20%.
Physical constants and characterization of 3-(2,5-
dimethylphenyl)-2-(2-chlorophenyl)-6-{2-[2-(2-
chlorophenyl)-4-oxo(3-hydroquinazolin-3-yl)]ethyl}-3-
hydroquinazolin-4-one (5e)
m.p.:245°C; yield: 65%; IR (KBr): 3093, 3064 (C–H str.,
aromatic ring), 2831 (C–H str., –CH2 group), 1719, 1736
(C=O str., amide group), 1657, 1613, (C=N, C=C, qui-
nazoline ring), 1354 (C–N str., quinazoline ring), 1529 (N–
O str., –NO2 group), 839 (C–Cl stretching); 1H NMR
(CDCl3): 6.57–7.84 (m, 18H, Ar–H). 2.55 (t, 2H, C–CH2),
3.55 (t, 2H, N–CH2), 2.40 (s, 3H, Ar–CH3), 2.24 (s, 3H,
Ar–CH3); 13C-NMR (CDCl3): 19.2, 24.3, 33.1, 43.1, 120.7,
120.8, 121.2, 122.3, 122.4, 123.0, 124.5, 127.0, 127.4,
127.5, 127.7, 128.8, 128.9, 129.1, 130.8, 131.3, 131.6,
132.4, 133.5, 135.4, 135.6, 138.0, 148.6, 151.2, 160.8,
161.1, 164.4; GCMS: m/z: 643.57 (100.0%) (M?); Anal.
Calc. For C38H28Cl2N4O2: C-70.92%, H-4.38%, N-8.70%.
Found: C-62.30%, H-3.16%, N-8.20%.
Physical constants and characterization of 2-(2-
chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)]ethyl}-3-(2-nitrophenyl)-3-
hydroquinazolin-4-one (5h)
m.p.:198°C; yield: 63%; IR (KBr): 3098, 3063 (C–H str.,
aromatic ring), 2839 (C–H str., –CH2 group), 1711, 1732
(C=O str., amide group), 1654, 1608, (C=N, C=C, qui-
nazoline ring), 1357 (C–N str., quinazoline ring), 1522 (N–
O str., –NO2 group), 831 (C–Cl stretching); 1H NMR
(CDCl3): 6.68–7.89 (m, 19H, Ar–H). 2.61 (t, 2H, C–CH2),
3.34 (t, 2H, N–CH2); GCMS: m/z: 660.51 (100.0%) (M?);
13C-NMR (CDCl3): 33.1, 43.1, 120.7, 120.8, 122.3, 122.4,
122.5, 123.0, 124.1, 125.3, 127.0, 127.4, 127.5, 127.7,
128.8, 128.9, 130.8, 131.6, 132.4, 133.3, 133.5, 136.1,
138.0, 142.4, 148.1, 151.2, 160.5, 161.6, 164.3; Anal. Calc.
For C36H23Cl2N5O4: C-65.46%, H-3.51%, N-10.60%.
Found: C-62.30%, H-3.16%, N-8.20%.
Physical constants and characterization of 2-(2-
chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)]ethyl}-3-(4-methoxy-2-
nitrophenyl)-3-hydroquinazolin-4-one (5f)
Physical constants and characterization of 2-(2-
chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)]ethyl}-3-(3-nitrophenyl)-3-
hydroquinazolin-4-one (5i)
m.p.:235°C; yield: 68%; IR (KBr): 3091, 3063 (C–H str.,
aromatic ring), 2836 (C–H str., –CH2 group), 1719, 1733
(C=O str., amide group), 1654, 1609, (C=N, C=C, qui-
nazoline ring), 1356 (C–N str., quinazoline ring), 1525 (N–
O str., –NO2 group), 836 (C–Cl stretching); 1H NMR
(CDCl3) : 6.67–7.83 (m, 18H, Ar–H). 2.61 (t, 2H, C–CH2),
3.39 (t, 2H, N–CH2), 3.91 (s, 3H, –OCH3); GCMS:
m/z: 690.94 (100.0%) (M?); 13C-NMR (CDCl3): 33.1,
43.1, 55.8, 110.1, 120.6, 120.7, 120.8, 122.3, 122.4,
123.0, 123.5, 125.6, 127.0, 127.4, 127.5, 127.7,
128.8, 128.9, 130.8, 131.6, 132.4, 133.5, 138.0, 143.4,
148.2, 151.2, 157.1, 160.8, 161.4, 164.2; Anal. Calc. For
C37H25Cl2N5O5: C-64.35%, H-3.14%, N-10.14%. Found:
C-62.30%, H-3.16%, N-8.20%.
m.p.:186°C; yield: 72%; IR (KBr): 3091, 3062 (C–H str.,
aromatic ring), 2832 (C–H str., –CH2 group), 1711, 1736
(C=O str., amide group), 1652, 1607, (C=N, C=C, qui-
nazoline ring), 1351(C–N str., quinazoline ring), 1523 (N–
O str., –NO2 group), 825 (C–Cl stretching); 1H NMR
(CDCl3): 6.59–7.92 (m, 19H, Ar–H). 2.58 (t, 2H, C–CH2),
3.32 (t, 2H, N–CH2); GCMS: m/z: 6 (100.0%) (M?); 13C-
NMR (CDCl3): 33.1, 43.1, 114.5, 119.5, 120.7, 120.8,
122.3, 122.4, 123.0, 127.0, 127.4, 127.5, 127.7, 128.8,
123

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Med Chem Res (2012) 21:1127–1135
128.9, 129.9, 130.8, 131.6, 132.4, 133.5, 133.6, 138.0,
148.1, 148.0, 151.2, 160.7, 161.4, 164.4; Anal. Calc. For
C36H23Cl2N5O4: C-65.46%, H-3.51%, N-10.60%. Found:
C-62.30%, H-3.16%, N-8.20%.
(CDCl3): 6.62–7.87 (m, 17H, Ar–H). 2.58 (t, 2H, C–CH2),
3.28 (t, 2H, N–CH2); GCMS: m/z: 538.98 (100.0%) (M?);
13C-NMR (CDCl3) : 33.1, 43.1, 120.7, 120.8, 122.3, 122.4,
122.5, 123.0, 127.0, 127.4, 127.5, 127.7, 128.8, 128.9,
130.8, 131.6, 132.4, 132.8, 133.5, 138.0, 145.1, 146.3,
148.2, 151.2, 160.9, 161.3, 164.2; Anal. Calc. For
C36H21Cl4N5O4: C-59.28%, H-2.90%, N-9.60%. Found:
C-62.30%, H-3.16%, N-8.20%.
Physical constants and characterization of 2-(2-
chlorophenyl)-6-{2-[2-(2-chlorophenyl)-4-oxo(3-
hydroquinazolin-3-yl)]ethyl}-3-(4-nitrophenyl)-3-
hydroquinazolin-4-one (5j)
Acknowledgments The authors express their sincere thanks to the
Department of Chemistry and to Bhavnagar University, Bhavnagar
for providing research facilities.
m.p.:230°C; yield: 68%; IR (KBr): 3090, 3061 (C–H str.,
aromatic ring), 2836 (C–H str., –CH2 group), 1714, 1732
(C=O str., amide group), 1651, 1611, (C=N, C=C, qui-
nazoline ring), 1353 (C–N str., quinazoline ring), 1522 (N–
O str., –NO2 group), 834 (C–Cl stretching); 1H NMR
(CDCl3): 6.67–7.97 (m, 19H, Ar–H). 2.61 (t, 2H, C–CH2),
3.37 (t, 2H, N–CH2); GCMS: m/z: 660.51 (100.0%) (M?);
13C-NMR (CDCl3): 33.1, 43.1, 120.7, 120.8, 122.3, 122.4,
122.5, 123.0, 124.1, 127.0, 127.4, 127.5, 127.7, 128.8,
128.9, 130.8, 131.6, 132.4, 133.5, 138.0, 138.8, 143.5,
148.6, 151.2, 160.4, 161.4, 164.3; Anal. Calc. For
C36H23Cl2N5O4: C-65.46%, H-3.51%, N-10.60%. Found:
C-62.30%, H-3.16%, N-8.20%.
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