Synthesis, characterization, antibacterial and antifungal activity of 2-(Aryl)-3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-ones

Article abstract of DOI:10.1002/jhet.788

5-((3-aminophenyl)diazenyl)quinolin-8-ol (1) was synthesized by diazotization reaction and coupled with 8-hydroxyquinoline moiety. This amine on facile condensation with aromatic aldehydes in presence of glacial acetic acid and ethanol affords anils (2).

Full text of DOI:10.1002/jhet.788

November 2011 Synthesis, Characterization, Antibacterial and Antifungal Activity
of 2-(Aryl)-3-(3-((8-hydroxyquinolin-5-
yl)diazenyl)phenyl)thiazolidin-4-ones
1323
Himani N. Chopde, Ramakanth Pagadala, Jyotsna S. Meshram,*
and Venkateshwarlu Jetti
Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur 440 033,
Maharashtra, India
*E-mail: drjsmeshram@rediffmail.com
Received August 7, 2010
DOI 10.1002/jhet.788
Published online 18 August 2011 in Wiley Online Library (wileyonlinelibrary.com).
5-((3-aminophenyl)diazenyl)quinolin-8-ol (1) was synthesized by diazotization reaction and coupled
with 8-hydroxyquinoline moiety. This amine on facile condensation with aromatic aldehydes in presence
of glacial acetic acid and ethanol affords anils (2). These anils on cyclocondensation reaction with thio-
glycolic acid (i.e., mercaptoacetic acid) yield the titled compound (3). The structure of the newly syn-
thesized anils (2) and thiazolidinones (3) has been confirmed by elemental analysis and spectral
analysis. The titled compounds have been screened against different bacterial and fungal strains.
J. Heterocyclic Chem., 48, 1323 (2011).
INTRODUCTION
importance of azo compounds is well known for their
use as antineoplastics [26], antidiabetics [27], antiseptics
[28], and other useful chemotherapeutic agents. It has
been found that the activity of azo linkage increases on
the incorporation of suitable heterocyclic moiety.
4-Thiazolidinones are one of the most intensively
investigated classes of aromatic five membered hetero-
cycles [29–32]. 4-Thiazolidinone derivatives exhibit
broad spectrum of biological activity [33–36]. Its deriva-
tives have been found to have potentially chemotherapic
activities such as anticonvulsant [37], antibacterial [38],
antifungal [39], anti-inflammatory [40], anticancer [41],
and antipsychotic [42] properties. Some of the reported
4-thiazolidinones have showed envelope or half-chair
conformation with different configurations [43]. Their
structural and conformational features are essential to
correlate to the biological activity. Because of this, the
investigation of chemistry and biology of these com-
pounds continue to appeal the synthetic and medicinal
organic chemists.
The chemistry of quinoline has gained increasing
attention due to its versatile pharmacological activities
[1–3]. Quinoline ring fused with five- or six-mem-
bered ring in linear fashion is found in natural prod-
ucts as well as in synthetic compounds of biological
interest. Dictemine and skimmianine are the examples
of such class of naturally occurring compounds,
which are associated with smooth muscle contracting
properties.
Quinolones are extensively investigated as broad
spectrum antibacterial [4,5], antidiabetic [6], anticancer
[7], antiviral [8], and anti-HIV [9] agents. Quinoline
family compounds are widely used as a parent com-
pound to make drugs especially antimalarial, fungicidal,
and biocidal medicines due to their versatile biological
activity. These properties are closely related with their
capability for chelating metallic ions [10].
8-Hydroxyquinoline or 8-quinolinol is well known as
an analytical reagent [11,12]. One of the derivatives, viz.
5-chloromethyl 8-quinolinol can be synthesize facilely
and studied extensively for number of derivatives [13].
Some of the ions exchanging resins are also reported
with good potentiality [14–23]. Several azo dyes based
on 8-quinolinol are also reported for dyeing of textiles
as well as their chelating properties [24,25]. Biological
With this background, it has been thought worth to
synthesize some novel heterocyclic compounds compris-
ing of thiazolidinone and azo-linkage in a single com-
pound and to undertake the systematic study of these
new compounds for their potency as an antibacterial and
antifungal agents.
C
V
2011 HeteroCorporation

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H. N. Chopde, R. Pagadala, J. S. Meshram, and V. Jetti
Vol 48
Scheme 1. Synthetic route for 2-(aryl)-3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl) thiazolidin-4-one.
RESULTS AND DISCUSSION
Biological Activity. Antibacterial activities of all the
compound (3) using DMSO as solvent were studied
against different bacterial strains such as E. coli, B.
subtilis, S. aureus, and P. vulageris, whereas antifungal
activity were checked against the C. albicans and A.
niger strains. The antibacterial and antifungal activities
of compound (3) were evaluated by measuring the
zone of inhibition on nutrient agar plates and Sabour-
In continuation of our efforts toward the synthesis
and biological evaluation of different heterocyclic
compounds [44–47], we, herein, report the synthesis of
2-(aryl)-3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thia-
zolidin-4-ones (3). The compound (1), that is, 5-((3-amino-
phenyl)diazenyl) quinolin-8-ol was synthesized by
a
simple azo-dye formation process. The condensation reac-
tion of compound (1) with various aromatic aldehydes
yields 5-((3-(arylbenzylideneamino)phenyl)diazenyl)quino-
lin-8-ol (2). Compound (2) on reaction with mercaptoace-
tic acid afford 2-(aryl)-3-(3-((8-hydroxyquinolin-5-yl)dia-
zenyl) phenyl)thiazolidin-4-one (3). The synthetic route to
obtain compound (3) has been summarized in Scheme 1.
Yields of the synthesized compounds (2 and 3) were found
to moderate to fair (60–85%). The purity of the com-
pounds was monitored by TLC and the structure of the
compounds was confirmed based on their elemental analy-
sis and spectral data.
´
audıs agar plates, respectively. The results were
recorded in duplicate using ampicillin as a standard
drug for antibacterial activity, whereas flucanazole as a
standard drug for antifungal activity. The study reveals
that compounds possess moderate to good activity
against all stains in comparison with standard drug
(Table 1).
MATERIALS AND METHODS
General. All the chemicals and solvents were obtained
from E-Merck, India (AR grade) and were used without further
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2011
Synthesis, Characterization, Antibacterial and Antifungal Activity of 2-(Aryl)-
3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-ones
1325
Table 1
Biological activities of 2-(aryl)-3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-one.
Antibacterial activity
(Zone of inhibition in mm at 500 lg/mL)
Antifungal activity
Compd.
E. coli
B. subtilis
S. aureus
P. vulageris
C. albicans
A. niger
3a
3b
3c
3d
3e
3f
3g
20
23
22
18
19
24
18
19
20
22
22
25
17
23
17
16
15
17
16
20
21
18
19
20
23
18
20
22
19
24
18
17
21
16
20
19
17
14
10
16
19
14
15
10
8
10
11
14
18
18
13
14
10
14
10
12
16
15
18
15
3h
3i
Standard Drug
purification. Melting points were taken in an open capillary
tube. IR spectra were recorded on a Shimadzu Dr-8031 instru-
ment. Elemental analyses were carried out using a Perkin-
tion mixture was poured in ice-cold water, and the solid pre-
cipitate was separated out. The precipitate was filtered out, and
the crude product was recrystallized from chloroform.
1
Elmer, CHN elemental analyzer model 2400. H NMR spectra
Characterization data of 5-((3-(benzylideneamino) phe-
nyl)diazenyl)quinolin-8-ol (2a). Yield: 74%, M.p.: 170ꢀC, IR
(KBr): 1460 cmꢁ1 (N¼¼N); 1618 (AC¼¼NA), 2990 cmꢁ1 (Ar-
of the synthesized compounds were recorded on a Bruker-
Avance (300 MHz) and Varian-Gemini (200 MHz) spectropho-
tometer using CDCl3 solvent and TMS as an internal standard.
EI-MS spectra were determined on a LCQ ion trap mass spec-
trometer (Thermo Fisher, San Jose, CA), equipped with an EI
source.
1
OH); H NMR: d ¼ 7.15–7.20 (d, 2H, Ar-CH); 7.50–7.60 (m,
6H, Ar-CH); 7.80 (t, 3H, Ar-CH); 8.00 (t, 1H, Ar-CH); 8.40
(d, 1H, Ar-CH); 8.60 (s, 1H, N¼¼CH); 8.90 (d, 1H, Ar-CH);
9.75 (s, 1H, Ar-OH); Anal. Calcd. For C22H16N4O: C, 74.98;
H, 4.58; N, 15.90; Found: C, 74.50; H, 4.10; N, 15.30; Mass
spectra, m/z ¼ 352.13 (100%).
Synthesis of 5-((3-aminophenyl)diazenyl)quinolin-8-ol (1). The
diazo salt solution of m-phenylenediamine was prepared by
simple diazotization reaction and then coupled with 8-hydroxy
quinoline moiety. 8-Hydroxy quinoline (0.01 mol) was dis-
solved in required amount of aqueous alkali, and the solution
was then cooled to 0–5ꢀC. To this well-stirred solution, the di-
azonium salt of m-phenylenediamine was added slowly, so that
temperature did not rise above 5ꢀC. While maintaining pH of
the reaction mixture within the range of 4.5–5.5 by the action
of sodium acetate solution (10% w/v), the mixture was then
stirred for 1 h at 0–5ꢀC. The resulting solid dye material was
filtered off, washed with boiling water, and then air-dried. It
was red amorphous powder. It is soluble in ethanol, chloro-
form, DMF, and DMSO. Melting point of compound (1) was
found to be 210ꢀC.
Characterization data of 5-((3-aminophenyꢁl)1diazenyl)
quinolin-8-ol (1). M.p.: 140ꢀC, IR (KBr): 1450 cm (N¼¼N);
2990 cmꢁ1 (Ar-OH); 3450 cmꢁ1 (Ar-NH2); 1H NMR: d ¼
5.30 (s, 2H, Ar-NH2) 6.80 (s, 1H, Ar-CH); 7.20–7.40 (m, 4H,
Ar-CH); 7.60 (t, 1H, Ar-CH); 7.80 (d, 1H, Ar-CH); 8.40 (d,
2H, Ar-CH); 8.90 (d, 1H, Ar-CH); 9.80 (s, 1H, Ar-OH);
Anal. Calcd. For C15H12N4O: C, 68.17; H, 4.58; N, 21.20;
Found: C, 68.00; H, 4.20; N, 21.10; Mass spectra, m/z ¼ 264
(100%).
Characterization data of 5-((3-(2-hydroxybenzylidene
amino)phenyl)diazenyl)quiꢁn1olin-8-ol (2b). Yield: 70%, M.p.:
178ꢀC, IR (KBr): 1478 cm (N¼¼N); 1625 (AC¼¼NA), 3015
cmꢁ1 (Ar-OH); 1H NMR: d ¼ 7.00–7.20 (m, 4H, Ar-CH);
7.50–7.65 (m, 5H, Ar-CH); 7.90 (s, 1H, Ar-CH); 8.10 (s, 1H,
Ar-CH); 8.30 (d, 2H, Ar-CH); 8.80 (s, 1H, N¼¼CH); 9.70 (s,
1H, Ar-OH); 11.20 (s, 1H, Ar-OH) Anal. Calcd. For
C22H16N4O2: C, 71.73; H, 4.38; N, 15.21; Found: C, 71.20; H,
4.20; N, 15.10; Mass spectra, m/z ¼ 368.13 (100%).
Characterization data of 5-((3-(4-methoxybenzylidene
amino)phenyl)diazenyl)quiꢁn1olin-8-ol (2c). Yield: 78%, M.p.:
175ꢀC, IR (KBr): 1480 cm (N¼¼N); 1630 (AC¼¼NA), 2986
1
cmꢁ1 (Ar-OH); H NMR: d ¼ 3.80 (s, 3H, Ar-OCH3) 7.00 (d,
2H, Ar-CH); 7.20 (d, 2H, Ar-CH); 7.60–7.70 (t, 3H, Ar-CH);
7.80 (t, 3H, Ar-CH); 8.00 (s, 1H, Ar-CH); 8.20 (d, 1H, Ar-
CH); 8.50 (s, 1H, N¼¼CH); 8.80 (s, 1H, Ar-CH); 9.60 (s, 1H,
Ar-OH); Anal. Calcd. For C23H18N4O2: C, 72.24; H, 4.74; N,
14.65; Found: C, 72.00; H, 4.30; N, 14.20; Mass spectra, m/z
¼ 382.10 (100%).
Characterization data of 5-((3-(4-(dimethylamino) benzylide-
neamino)phenyl)diazenyl)quꢁin1olin-8-ol (2d). Yield: 62%, M.p.:
168ꢀC, IR (KBr): 1470 cm (N¼¼N); 1650 (AC¼¼NA), 2965
1
Synthesis of 5-((3-(arylbenzylideneamino)phenyl) diaze-
nyl)quinolin-8-ol (2a–i). Equimolar amount of 5-((3-amino-
phenyl)diazenyl)quinolin-8-ol (1) (0.01 mol) and aromatic
aldehyde (0.01 mol) and two to three drops of glacial acetic
acid in ethanol (10 mL) was refluxed for 3–4 h. The reaction
was monitored by TLC. After completion of the reaction, the
reaction mixture was set on one side to cool. Then, the reac-
cmꢁ1 (Ar-OH); H NMR: d ¼ 3.06 (s, 6H, N(CH3)2) 6.80 (d,
2H, Ar-CH); 7.30 (d, 2H, Ar-CH); 7.50 (d, 2H, Ar-CH); 7.60
(d, 2H, Ar-CH); 7.70 (s, 1H, Ar-CH); 7.80(s, 1H, Ar-CH);
8.00(s, 1H, Ar-CH); 8.30 (s, 1H, Ar-CH); 8.70 (s, 1H, N¼¼CH);
8.90 (s, 1H, Ar-CH); 9.75 (s, 1H, Ar-OH); Anal. Calcd. For
C24H21N5O: C, 72.89; H, 5.35; N, 17.71; Found: C, 72.50; H,
5.10; N, 17.20; Mass spectra, m/z ¼ 395.10 (100%).
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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H. N. Chopde, R. Pagadala, J. S. Meshram, and V. Jetti
Vol 48
8.40 (s, 1H, Ar-CH); 8.80 (s, 1H, Ar-CH); 9.50 (s, 1H, Ar-OH);
Anal. Calcd. For C24H18N4O2S: C, 67.59; H, 4.25; N, 13.14; S,
7.52; Found: C, 67.20; H, 4.10; N, 13.00; S, 7.35; Mass spectra,
m/z ¼ 426 (100%).
Characterization data of 5-((3-(4-hydroxybenzylidene
amino)phenyl)diazenyl)quiꢁn1olin-8-ol (2e). Yield: 75%, M.p.:
165ꢀC, IR (KBr): 1450 cm (N¼¼N); 1640 (AC¼¼NA), 2960
cmꢁ1 (Ar-OH); 1H NMR: d ¼ 6.80 (d, 2H, Ar-CH); 7.20 (d,
2H, Ar-CH); 7.60–7.80 (m, 6H, Ar-CH); 8.10 (s, 1H, Ar-CH);
8.30 (s, 1H, Ar-CH); 8.70 (s, 1H, N¼¼CH); 8.90 (s, 1H, Ar-
CH); 9.40(s, 1H, Ar-OH); 9.70 (s, 1H, Ar-OH); Anal. Calcd.
For C22H16N4O2: C, 71.73; H, 4.38; N, 15.21; Found: C, 71.10;
H, 4.20; N, 15.00; Mass spectra, m/z ¼ 368.10 (100%).
Characterization data of 2-(2-hydroxyphenyl)-3-(3-((8-hydrox-
yquinolin-5-yl)diazenyl) phenyl)thiazo lidin-4-one (3b). Yield:
65%; M.p.: 190ꢀC, IR (KBr): 690 (CASAC, 4-thiazolidi-
none), 756 (1, 2 disubstituted benzene ring), 1253 (CAN),
1483 (C¼¼C), 1608 (C¼¼O, thiazolidinone), 2363 (Ar-CH),
3067 cmꢁ1 (Ar-OH); 1H NMR: d ¼ 3.90 (m, 2H, Ar-CH);
6.30 (s, 1H, Ar-CH); 6.80 (d, 2H, Ar-CH, thiazolidinone);
7.00 (d, 2H, Ar-CH); 7.20 (s, 1H, Ar-CH); 7.30 (s, 1H, Ar-
CH); 7.60 (d, 2H, Ar-CH); 7.80 (s, 1H, Ar-CH); 7.90 (d, 2H,
Ar-CH); 8.40 (s, 1H, Ar-CH); 8.90 (s, 1H, Ar-CH); 9.60(s,
1H, Ar-OH); 9.70 (s, 1H, Ar-OH); Anal. Calcd. For
C24H18N4O3S: C, 65.14; H, 4.10; N, 12.66; S, 7.25; Found:
C, 65.00; H, 4.00; N, 12.16; S, 7.25; Mass spectra, m/z ¼
442 (100%).
Characterization data of 5-((3-(3-nitrobenzylidene ami-
no)phenyl)diazenyl)quinoliꢁn1-8-ol (2f). Yield: 82%, M.p.:
175ꢀC, IR (KBr): 1445 cm (N¼¼N); 1660 (AC¼¼NA), 2975
1
cmꢁ1 (Ar-OH); H NMR: d ¼ 7.20 (d, 2H, Ar-CH); 7.60–7.80
(m, 5H, Ar-CH); 8.00 (s, 1H, Ar-CH); 8.20(d, 2H, Ar-CH);
8.40 (s, 1H, Ar-CH); 8.50 (s, 1H, Ar-CH); 8.70 (s, 1H,
N¼¼CH); 8.85 (s, 1H, Ar-CH); 9.80 (s, 1H, Ar-OH); Anal.
Calcd. For C22H15N5O3: C, 66.49; H, 3.80; N, 17.62; Found: C,
66.30; H, 3.20; N, 17.10; Mass spectra, m/z ¼ 397.10 (100%).
Characterization data of 5-((3-(2-nitrobenzylidene ami-
no)phenyl)diazenyl)quinoliꢁn1-8-ol (2g). Yield: 70%, M.p.:
180ꢀC, IR (KBr): 1460 cm (N¼¼N); 1680 (AC¼¼NA), 2985
Characterization data of 3-(3-((8-hydroxyquinolin-5-yl)dia-
zenyl)phenyl)-2-(4-methoxyphenyl)thiazolidin-4-one (3c). Yield:
75%; M.p.: 180ꢀC, IR (KBr): 680 (CASAC, 4-thiazolidinone),
750 (1, 2 disubstituted benzene ring), 1250 (CAN), 1480
(C¼¼C), 1620 (C¼¼O, thiazolidinone), 2360 (Ar-CH), 3060
cmꢁ1 (Ar-OH); 1H NMR: d ¼ 3.80 (s, 3H, Ar-OCH3); 3.90
(d, 2H, Ar-CH); 6.40 (s, 1H, Ar-CH); 6.80 (d, 2H, Ar-CH,
thiazolidinone); 7.20 (s, 1H, Ar-CH); 7.60 (t, 1H, Ar-CH);
7.70 (d, 2H, Ar-CH); 7.80 (t, 3H, Ar-CH); 7.90 (d, 2H, Ar-
CH); 8.40 (s, 1H, Ar-CH); 8.90 (s, 1H, Ar-CH); 9.80 (s, 1H,
Ar-OH); Anal. Calcd. For C25H20N4O3S: C, 65.77; H, 4.42;
N, 12.27; S, 7.02; Found: C, 65.40; H, 4.10; N, 12.00; S,
6.85; Mass spectra, m/z ¼ 456.10 (100%).
1
cmꢁ1 (Ar-OH); H NMR: d ¼ 7.10 (d, 2H, Ar-CH); 7.50–7.70
(m, 4H, Ar-CH); 7.80–8.10 (m, 5H, Ar-CH); 8.30(s, 1H, Ar-
CH); 8.80 (s, 1H, N¼¼CH); 8.90 (s, 1H, Ar-CH); 9.70 (s, 1H,
Ar-OH); Anal. Calcd. For C22H15N5O3: C, 66.49; H, 3.80; N,
17.62; Found: C, 66.10; H, 3.00; N, 17.30; Mass spectra, m/z
¼ 397.00 (100%).
Characterization data of 5-((3-(4-chlorobenzylidene ami-
no)phenyl)diazenyl)quinoliꢁn1-8-ol (2h). Yield: 80%, M.p.:
182ꢀC, IR (KBr): 1476 cm (N¼¼N); 1630 (AC¼¼NA), 2998
1
cmꢁ1 (Ar-OH); H NMR: d ¼ 7.30 (d, 2H, Ar-CH); 7.50–7.80
Characterization data of 2-(4-(dimethylamino)phenyl)-3-
(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl) thiazolidin-4-
one (3d). Yield: 60%; M.p.: 175ꢀC, IR (KBr): 660 (CASAC,
4-thiazolidinone), 730 (1, 2 disubstituted benzene ring), 1220
(CAN), 1450 (C¼¼C), 1630 (C¼¼O, thiazolidinone), 2380 (Ar-
CH), 3260 cmꢁ1 (Ar-OH); 1H NMR: d ¼ 3.10 (s, 6H,
N(CH3)2); 3.80 (d, 2H, Ar-CH); 6.50 (s, 1H, Ar-CH); 6.70 (d,
2H, Ar-CH, thiazolidinone); 7.10 (d, 2H, Ar-CH); 7.20 (s, 1H,
Ar-CH); 7.40 (d, 2H, Ar-CH); 7.70 (s, 1H, Ar-CH); 7.80 (s, 1H,
Ar-CH); 7.90 (d, 2H, Ar-CH); 8.40 (s, 1H, Ar-CH); 8.90 (s, 1H,
Ar-CH); 9.80 (s, 1H, Ar-OH); Anal. Calcd. For C26H23N5O2S:
C, 66.50; H, 4.94; N, 14.91; S, 6.83; Found: C, 66.20; H, 4.20;
N, 14.30; S, 6.55; Mass spectra, m/z ¼ 469.10 (100%).
(m, 8H, Ar-CH); 8.10 (s, 1H, Ar-CH); 8.30(s, 1H, Ar-CH);
8.50 (s, 1H, N¼¼CH); 8.90 (s, 1H, Ar-CH); 9.90 (s, 1H, Ar-
OH); Anal. Calcd. For C22H15 ClN4O: C, 68.31; H, 3.91; N,
14.48; Found: C, 68.00; H, 3.40; N, 14.20; Mass spectra, m/z
¼ 386.00 (100%).
Characterization data of 5-((3-(2-chlorobenzylidene ami-
no)phenyl)diazenyl)quinoliꢁn1-8-ol (2i). Yield: 78%, M.p.:
185ꢀC, IR (KBr): 1470 cm (N¼¼N); 1670 (AC¼¼NA), 2995
1
cmꢁ1 (Ar-OH); H NMR: d ¼ 7.20 (d, 2H, Ar-CH); 7.30–7.80
(m, 8H, Ar-CH); 8.00 (s, 1H, Ar-CH); 8.40(s, 1H, Ar-CH); 8.80
(s, 1H, N¼¼CH); 9.10 (s, 1H, Ar-CH); 9.80 (s, 1H, Ar-OH); Anal.
Calcd. For C22H15 ClN4O: C, 68.31; H, 3.91; N, 14.48; Found: C,
68.10; H, 3.50; N, 14.00; Mass spectra, m/z ¼ 385.90 (100%).
Synthesis of 2-(aryl)-3-(3-((8-hydroxyquinolin-5-yl) diaze-
nyl)phenyl)thiazolidin-4-one (3a-i). Equimolar amount of
Schiff base (0.002 mol) and thioglycolic acid (0.002 mol) was
dissolved in ethanol (10 mL), and the reaction mixture was
refluxed for 12 h. The completion of the reaction was moni-
tored by TLC. After the completion of reaction, it was poured
in ice-cold water, and the solid precipitate was separated out.
The solid deposited was separated by filtration. The crude
product obtained was recrystallized from chloroform.
Characterization data of 2-(4-hydroxyphenyl)-3-(3-((8-
hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-one
(3e). Yield: 72%; M.p.: 175ꢀC, IR (KBr): 680 (CASAC, 4-
thiazolidinone), 735 (1, 2 disubstituted benzene ring), 1233
(CAN), 1460 (C¼¼C), 1640 (C¼¼O, thiazolidinone), 2340 (Ar-
CH), 3120 cmꢁ1 (Ar-OH); 1H NMR: d ¼ 4.00 (m, 2H, Ar-
CH); 6.30 (s, 1H, Ar-CH); 6.60 (d, 2H, Ar-CH, thiazolidi-
none); 7.30 (s, 1H, Ar-CH); 7.40 (s, 1H, Ar-CH); 7.60–7.80
(m, 5H, Ar-CH); 8.00 (d, 2H, Ar-CH); 8.40 (s, 1H, Ar-CH);
8.90 (s, 1H, Ar-CH); 9.40(s, 1H, Ar-OH); 9.80 (s, 1H, Ar-
OH); Anal. Calcd. For C24H18N4O3S: C, 65.14; H, 4.10; N,
12.66; S, 7.25; Found: C, 64.90; H, 4.05; N, 12.40; S, 7.15;
Mass spectra, m/z ¼ 442.10 (100%).
Characterization data of 3-(3-((8-hydroxyquinolin-5-
yl)diazenyl)phenyl)-2-phenylthiazolidin-4-one(3a). Yield:
70%; M.p.: 160ꢀC, IR (KBr): 660 (CASAC, 4-thiazolidinone),
736 (1, 2 disubstituted benzene ring), 1220 (CAN), 1440
(C¼¼C), 1610 (C¼¼O, thiazolidinone), 2370 (Ar-CH), 3110 cmꢁ1
(Ar-OH); 1H NMR: d ¼ 3.90–4.00 (m, 2H, Ar-CH); 6.40 (s,
1H, Ar-CH); 7.20–7.30 (m, 6H, Ar-CH, thiazolidinone); 7.60–
7.70 (t, 3H, Ar-CH); 7.80 (s, 1H, Ar-CH); 7.90 (d, 2H, Ar-CH);
Characterization data of 3-(3-((8-hydroxyquinolin-5-yl)diaze-
nyl)phenyl)-2-(3-nitrophenyl)thiazolidin-4-one (3f). Yield:
80%; M.p.: 190ꢀC, IR (KBr): 620 (CASAC, 4-thiazolidinone),
760 (1, 2 disubstituted benzene ring), 1240 (CAN), 1470
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

November 2011
Synthesis, Characterization, Antibacterial and Antifungal Activity of 2-(Aryl)-
3-(3-((8-hydroxyquinolin-5-yl)diazenyl)phenyl)thiazolidin-4-ones
1327
REFERENCES AND NOTES
(C¼¼C), 1670 (C¼¼O, thiazolidinone), 2980 (Ar-CH), 3270
cmꢁ1 (Ar-OH); 1H NMR: d ¼ 4.10 (d, 2H, Ar-CH); 6.30 (s,
1H, Ar-CH); 7.10 (s, 1H, Ar-CH, thiazolidinone); 7.40 (s, 1H,
Ar-CH); 7.50–7.80 (m, 5H, Ar-CH); 7.95–8.10 (m, 4H, Ar-
CH); 8.40 (s, 1H, Ar-CH); 8.90 (s, 1H, Ar-CH); 9.80 (s, 1H,
Ar-OH); Anal. Calcd. For C24H17N5O4S: C, 61.14; H, 3.63;
N, 14.85; S, 6.80; Found: C, 59.90; H, 3.50; N, 14.20; S,
6.30; Mass spectra, m/z ¼ 471 (100%).
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Characterization data of 3-(3-((8-hydroxyquinolin-5-yl)dia-
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67%; M.p.: 172ꢀC, IR (KBr): 640 (CASAC, 4-thiazolidinone),
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77%; M.p.: 165ꢀC, IR (KBr): 680 (CASAC, 4-thiazolidinone),
710 (1, 2 disubstituted benzene ring), 1280 (CAN), 1420
(C¼¼C), 1640 (C¼¼O, thiazolidinone), 2960 (Ar-CH), 3190
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75%; M.p.: 185ꢀC, IR (KBr): 670 (CASAC, 4-thiazolidinone),
730 (1, 2 disubstituted benzene ring), 1250 (CAN), 1470
(C¼¼C), 1690 (C¼¼O, thiazolidinone), 2930 (Ar-CH), 3220
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In summary, we have synthesized some bioactive
thiazolidinones having 8-hydroxyquinoline moiety. The
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activity. Hence, these bioactive thiazolidinones can be
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Acknowledgments. The authors greatly acknowledge to Head
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

1328
H. N. Chopde, R. Pagadala, J. S. Meshram, and V. Jetti
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