Synthesis and antimicrobial assay of some novel 4-thiazolidinone derivatives possessing benzofuran, quinoline and pyrazole moieties

Article abstract of DOI:10.14233/ajchem.2018.21522

In this study, simple, easy and convenient syntheses of six novel 4-thiazolidinone derivatives (3a-f) bearing benzofuran, quinoline and pyrazole moieties have been described. In the first step, six different carbohydrazides (2a-f) were synthesized by reacting 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (2) with six different 2-(p-tolyloxy)quinoline-3-carbaldehyde (1a-f). Similarly, in second step, 5-(benzofuran-2-yl)-N′-(2-(2-(p-tolyloxy) substituted quinolin-3-yl)-4-oxothiazolidin-3-yl)-1-phenyl-1H-pyrazole-3-carboxamide (3a-f) was prepared in excellent yield through the interaction of compounds 2a-f with thioglycolic acid in presence of anhydrous zinc chloride. Structural identifications of products 2a and 3a are reported on the basis of IR,¹H NMR,¹³C NMR and mass spectra and the analytical data confirms the structure of title compounds. Further, these new products have been assayed for their antimicrobial screening against S. aureus and E. coli as the two selected bacterial strains and two fungi such as C. albicans and A. Niger using paper disc diffusion method. Antimicrobial screening revealed that the compounds are good antibacterial agents but found to be inactive against fungi.

Full text of DOI:10.14233/ajchem.2018.21522

Asian Journal of Chemistry; Vol. 30, No. 10 (2018), 2361-2364
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2018.21522
Synthesis and Antimicrobial Assay of Some Novel 4-Thiazolidinone Derivatives
Possessing Benzofuran, Quinoline and Pyrazole Moieties
1,*
2
1
M. IDREES , Y.G. BODKHE and N.J. SIDDIQUI
1Department of Chemistry, Government Institute of Science, Nagpur-440 001, India
2Department of Chemistry, Government Science College, Gadchiroli-442 605, India
*Corresponding author: E-mail: idreesshaikh.2009@gmail.com
Received: 16 June 2018;
Accepted: 20 July 2018;
Published online: 31 August 2018;
AJC-19075
In this study, simple, easy and convenient syntheses of six novel 4-thiazolidinone derivatives (3a-f) bearing benzofuran, quinoline and
pyrazole moieties have been described. In the first step, six different carbohydrazides (2a-f) were synthesized by reacting 5-(benzofuran-
2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (2) with six different 2-(p-tolyloxy)quinoline-3-carbaldehyde (1a-f). Similarly, in second
step, 5-(benzofuran-2-yl)-N′-(2-(2-(p-tolyloxy) substituted quinolin-3-yl)-4-oxothiazolidin-3-yl)-1-phenyl-1H-pyrazole-3-carboxamide (3a-f)
was prepared in excellent yield through the interaction of compounds 2a-f with thioglycolic acid in presence of anhydrous zinc chloride.
Structural identifications of products 2a and 3a are reported on the basis of IR, 1H NMR, 13C NMR and mass spectra and the analytical
data confirms the structure of title compounds. Further, these new products have been assayed for their antimicrobial screening against S.
aureus and E. coli as the two selected bacterial strains and two fungi such as C. albicans and A. niger using paper disc diffusion method.
Antimicrobial screening revealed that the compounds are good antibacterial agents but found to be inactive against fungi.
Keywords: Quinoline, Carbohydrazides, Thiazolidinone, Pyrazole, Antibacterial activity.
group at fourth position and methylene carbon atom at fifth
position is found to be more nucleophilic, hence, electrophilic
substitution may occur at this position. Thiazolidinone scaffold
is a better pharmacophore showing various biological activities
such as anti-inflammatory, analgesic [7], antitubercular [8-10],
antifungal [9], inhibitory [11], antioxidant [12,13], antihyper-
glycemic [14], antimycobacterial [15], antibacterial [16-18],
cytotoxic [19,20], antiviral [21], antiparkinsnian [22], antinfective
[23]. Toxoplasma gondii infection was studied for 4-thiazoli-
dinone [24]. This amazing array of applications and ubiquitous
biological importance of quinoline along with thiazolidinones
led us to synthesize a new series of 4-thiazolidinone analogues
containing benzofuran, quinoline and pyrazole moiety and
evaluate their antimicrobial activities.
INTRODUCTION
The synthesis of polysubstituted quinoline and its derivatives
is the focus of a large number of pharmacological studies because
of their wide range of biological applications. The quinoline
moiety constitutes the main framework of several natural products
such as Montelukast and Skimmianine. Quinoline was synthe-
sized by Vilsmeier-Haack reagent which is a versatile reagent
used in various synthetic transformation [1]. Quinine, amodia-
quine, piperaquine, orimaquine, mefloquine and chloroquine
are used as antimalarial drugs mainly consist quinoline moiety
[2]. Quinoline nucleus shows good antitumor [3] and antifungal
[4] activities. It is also reported that coordination polymer of
quinoline ligand too showed antimicrobial activity [5].Antimi-
crobial screening and molecular docking studies of some
triazoloquinazolinone [6] has also been studied.
EXPERIMENTAL
On the other hand, thiazolidinones are also an important class
of heterocyclic compounds which has been classified as 2,4,5-
thiazolidinones depending on the position of carbonyl group.
Out of these 4-thiazolidinone is a five member ring with carbonyl
The melting points of newly synthesized compounds were
determined in open capillary paraffin oil bath and found to be
uncorrected. H NMR spectra was recorded on Bruker AM
1
400 instrument using tetramethylsilane as an internal reference
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2362 Idrees et al.
Asian J. Chem.
and DMSO-d6 as solvent. IR spectra were recorded on a
Shimadzu IR 8400 Spectrophotometer with the frequency
ranging from 4000-400 cm-1. Mass spectra were obtained with
a Waters Micro mass Q-TOF Micro, Mass Spectrophotometer.
Elemental analysis was performed using Thermo Scientific
(Flash-2000). All the chemicals used were of AR grade of
Merck, S.D. Fine and Aldrich.
General procedure for synthesis of 5-(benzofuran-2-
yl)- N′-((6-methyl-2-(p-tolyloxy)quinolin-3-yl)methylene)-
1-phenyl-1H-pyrazole-3-carbohydrazide (2a) : 5-(benzo-
furan-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (2, 0.01
mol) and 6-methyl-2-(p-tolyloxy) quinoline-3-carbaldehyde
(1a) were dissolved in ethanol and then 2-3 drops of acetic
acid were added and the reaction mixture was refluxed for 2 h.
Resulting mass was cooled and poured into crushed ice, filtered
and further purified by recrystallization using 1,4-dioxane to
give 2a. Similarly, other derivatives 2a-f were synthesized by
by applying the same procedure as adopted for the synthesis
of 2a (Scheme-I).
Yield: 88 %. IR (KBr, νmax, cm-1): 3944, 3392, 3318, 3147 (N-H
str.), 3061 (C-H str., arom.), 2956, 2920 (C-H asym. str., aliph.),
2803 (C-H str. sym., aliph.), 1689 (C=O str. amide), 1580, 1505
(C=N), 1247 (C-O-C sym. str., ether), 1087, 1037 (C-O-C asym.
str., ether); Elemental analysis (%) calcd. (found) C37H29N5O4:
N, 11.53 (11.58).
5-(Benzofuran-2-yl)-N′-((8-methoxy-2-(p-tolyloxy)-
quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbo-
hydrazide (2d): Yellow crystalline solid; m.p. 228-232 ºC,
Yield: 83%. Elemental analysis (%) calcd. (found) C36H27N5O4:
N, 11.80 (11.84).
5-(Benzofuran-2-yl)-N′-((7-methoxy-2-(p-tolyloxy)-
quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbo-
hydrazide (2e) : Yellow crystalline solid; m.p. 228-231 ºC;
Yield: 79 %. Elemental analysis (%) calcd. (found) C36H27N5O4:
N, 11.80 (11.88).
5-(Benzofuran-2-yl)-N′-((6-methoxy-2-(p-tolyloxy)-
quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbo-
hydrazide (2f):Yellow crystalline solid; m.p. 258-261 ºC,Yield:
79 %. Elemental analysis (%) calcd. (found) C36H27N5O4: N,
11.80 (11.88).
O
Ph
Synthesis of 5-(benzofuran-2-yl)-N′-(2-(6-methyl-2-(p-
tolyloxy) quinoline-3-yl)-4-oxothiazolidin-3-yl)-1-phenyl-
1H-pyrazole-3-carboxamide (3a): To a mixture of 5-(benzo-
furan-3-yl)-N′-((6-methyl-2-(p-tolyloxy)quinolin-3-yl)methyl-
ene)-1-phenyl-4,5-dihydro-1H-pyrazole-3-carbohydrazide)
(2a, 0.02mol) and thioglycolic acid in 1,4-dioxane, anhydrous
ZnCl2 was added and then the reaction content was refluxed
for 8 h. The reaction mixture was kept overnight after addition
of 10 % sodium bicarbonate to neutralize thioglycolic acid.
The solution was stirred and product was separated out was
filtered, washed and recrystallized from 1,4-dioxane to get 3a.
Brown, crystalline solid; m.p. 178-180 ºC; Yield: 85 %. IR
(KBr, νmax, cm-1): 3228(N-H str. amide), 3061 (C-H str., arom.),
1005,1027(C-H i.p.def, arom.), 808 (C-H o.o.p. def. arom.),
1498, 1527 (C=C str. arom.), 1595 (C=N str., quinoline ring),
1673 (C=O amide str.), 1027, 1073 (C-O-C asym. str., ether),
1257, 1208 (C-O-C sym. str., ether), 1673 (C=O str. thiazolidi-
none ring), 1208 (C-N str. thiazolidinone ring), 696 (C-S-C str.
thiazolidinone ring). 1H NMR (DMSO-d6) δ ppm: 2.35 (s, 6H,
two CH3 group attached to two different aromatic ring), 3.58
(s, 2H, CH2 of thiazolidinone ring), 6.48 (s, 1H, at C2 of thiazolidi-
none ring), 6.49 (s, 1H, at C4 of pyrazole ring), 8.30 (s, 1H, at
C4 of quinoline ring), 10.41 (s, 1H, NH of -CONH- linkage),
6.38-7.67 (m, 17 H, arom. and heterocycl.). 13C NMR (δ ppm):
21 (CH3), 38 (C2 of thiazolidinone), 48 (C5 of thiazolidinone),
105, 106, 107, 110, 121, 123, 125, 127, 129, 135, 139, 144, 145,
153,159,167 (carbon of -CONH). Mass spectra m/z 652 [M + H]+,
674 [M + Na]+. Elementalanalysis(%)calcd. (found)C38H29N5O4S:
C, 70.03 (70.08); H, 4.49 (4.54); N, 10.75 (10.72); S, 4.92 (4.98).
Similarly, other compounds 3b-f of this series was prepared
by adopting the same procedure followed for compound 3a.
Their structures were established on the basis of elemental
and physical data (Table-1).
N
H
N
R
H
N
+
N
O
O
NH2
O
1a-f
2
AcOH, 2-3 drops
HO
Entry
R
a
b
c
d
e
f
6-CH3
8-CH3
6-OC2H5
8-OCH3
7-OCH3
6-OCH3
R
N
O
Ph
N
N
H
N
N
O
2a-f
O
Scheme-I
5-(Benzofuran-2-yl)-N′-((6-methyl-2-(p-tolyloxy)-
quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbo-
hydrazide (2a): Yellow crystalline solid; m.p. 263-265 ºC;
Yield: 81%; IR (KBr, νmax, cm-1): 3293, 3412, (N-H str.), 3062,
3029 (C-H str., arom.), 2958 (C-H asym. str., aliph.), 2857,
2915 (C-H str. sym., aliphatic), 1688 (C=O str.), 1650-1600
(C=N str.), 1240 (C-O-C sym. str., ether), 1058 (C-O-C asym.
str., ether); 1H NMR (DMSO-d6) δ ppm: 2.36 (s, 3H,Ar-CH3),
2.47 (s, 3H, CH3 attached to quinoline ring), 6.51 (s, 1H, at C4
of pyrazole ring), 12.21 (s, 1H, NHCO), 7.14-9.08 (m, 19H, arom.
+ heterocycl. ring protons); MS: m/e 577 M+, 578 [M + H]+,
579 [M + 2]+, 600 [M + Na]+. Elemental analysis (%) calcd. (found)
C36H27N5O3: C, 74.85 (74.05); H, 4.71 (4.50); N, 12.12 (12.06).
5-(Benzofuran-2-yl)-N′-((8-methyl-2-(p-tolyloxy)quino-
lin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbohydra-
zide (2b):Yellow crystalline solid; m.p. 234-238 ºC;Yield: 88 %.
Elementalanalysis(%)calcd. (found)C36H27N5O3: N, 12.12(12.16).
5-(Benzofuran-2-yl)-N′-((6-ethoxy-2-(p-tolyloxy)-
quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbo-
hydrazide (2c): Yellow crystalline solid; m.p. 260-264 ºC;
Antimicrobial activity:All the compounds were screened
in vitro for their antibacterial and antifungal activities at
concentration of 1000 µg/mL. Out of all the six synthesized
compounds 2a and 3a were then assayed at different concen-

Vol. 30, No. 10 (2018)
Synthesis and Antimicrobial Assay of Some Novel 4-Thiazolidinone Derivatives 2363
TABLE-1
PHYSICAL AND ANALYTICAL DATA OF SYNTHESIZED COMPOUNDS 3b-f
Elemental analysis (%): Found (calcd.)
Entry
R
Colour
Recrys. solvent
m.p. (°C)
Yield (%)
m.f.
N
S
3b
3c
3d
3e
3f
8-CH3
6-OC2H5
8-OCH3
7-OCH3
6-OCH3
Brown
Brown
Brown
Brown
Brown
1,4-Dioxane
1,4-Dioxane
1,4-Dioxane
1,4-Dioxane
1,4-Dioxane
184-190
234-238
220-224
203-207
244-250
75
80
76
75
75
C38H29N5O4S
C39H31N5O5S
C38H29N5O5S
C38H29N5O5S
C38H29N5O5S
10.82 (10.75)
10.32 (10.27)
10.48 (10.49)
10.45 (10.49)
10.51 (10.49)
4.91 (4.92)
4.73 (4.70)
4.82 (4.80)
4.78 (4.80)
4.79 (4.80)
tration ranging from 1000 to 63 µg/mL using disc diffusion
method. Initially, stock culture of S. aureus and E. coli were
revived by inoculating in broth media at 37 ºC for 18 h.The agar
plate of nutrient agar media was prepared and sterilized. After
the inoculation of bacterial cultural, the discs were dipped in the
different concentration of compound, which was prepared in
DMSO and placed on the surface of agar plate. All the plates
were incubated for 37 ºC for 24 h and diameter of zone of inhi-
bition were noted in mm. The results were compared with standard
drug Chloramphenicol. Same procedure was applied for A. niger
and C. albicans and results were compared with standard drug
Amphotericin.
another at 2.47ppm due to CH3 group attached to quinoline
moiety. Proton present on the pyrazole ring at C4 carbon gave
singlet at 6.51ppm, another downfield singlet appear at 12.21
ppm due to one proton of NH of NHCO group and multiplet
exhibited in the range of 7.14-9.08 ppm are due to nineteen
protons present on aromatic and heterocyclic ring. Thus 1H NMR
spectrum of compound 2a is in good agreement with the number
of protons present in the molecular formula C36H27N5O3.
The resulted compounds 2a-f were then reacted with thiogly-
colic acid in the presence of anhydrous ZnCl2 and cyclized
successfully to five-membered 4-thiazolidinones ring (3a-f)
in good to moderate yield and were recrystallized by 1,4-dioxane
(Table-1). All the synthesized compounds 3a-f was tested for
nitrogen and sulphur which gave positive result confirming
the presence of these extra elements in thiazolidinone ring.
The IR spectrum of compound 3a showed characteristics
absorption bands at 3228 cm-1 due to NH stretch.Another absor-
ption band appeared at 1673 cm-1 assigned due to C=O stretch-
ing in thiazolidinone ring.Another characteristic band appeared
at 696 cm-1 due to C-S-C stretch confirmed the formation of
thiazolidinone ring. 1H NMR spectra for compound 3a exhi-
bited singlet at 2.35 ppm due to six protons of two CH3 group
attached to phenyl and quinoline ring. Other signals for aromatic
protons appeared at expected region. Singlet at 3.58 and 6.48 ppm
for two protons and one proton for CH2 and CH group, respec-
tively were observed which was absent in compound 2a, this
confirms the formation of thiazolidinone ring.A singlet appeared
at 8.30 ppm due to one proton of NH of -CONH- linkage. Singlet
due to one proton located at C4 of quinoline ring was also observed
in expected region in compound 3a as observed for compound
2a. Two characteristics 13C NMR signals appeared at 38 and 48
ppm is assigned due to carbon atom at second and fifth position
of thiazolidinone ring and signals due to other aromatic and
aliphatic carbons appeared at the expected region. The mass
spectra of compound 3a gives a molecular ion peak of [M + H]+
at 652 and [M + Na]+ at 674, is in good agreement with the
molecular formula C38H29N5O4S.
RESULTS AND DISCUSSION
Synthetic work was performed as described in Schemes
I and II and their purity was checked by TLC. The compounds
were obtained in excellent yield and structures have been
confirmed by elemental analysis and IR, 1H NMR and mass
spectral studies. 2-Chloroquinoline-3-carbaldehyde derivatives
were the starting compounds which were prepared byVilsmeier
cyclization [1], which later on reaction with p-cresol in presence
of K2CO3 in DMF yielded substituted 2-phenoxyquinoline-3-
carbaldehyde derivatives (1a-f). Treatment of compounds 1a-f
with 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohy-
drazide (2) yielded 5-(benzofuran-2-yl)-N′-((2-(p-tolyloxy)-
substituted quinolin-3-yl)methylene)-1-phenyl -1H-pyrazole-
3-carbohydrazides (2a-f) as illustrated in Scheme-I.
The IR spectra of compounds 2a and 2c showed a broad
signal of NH at 3293, 3412 and 3318 cm-1 respectively. The
absorption bands at 1688 and 1689 cm-1 are due to C=O stret-
ching also observed. Similarly, peak at 1580 in compound 2c
and 1650-1600 cm-1 in compound 2a are due to C=N stretching
in pyrazole ring further supported the structure of compounds
2c and 2a. Molecular ion peaks of [M + H]+, in mass spectra
1
at 578 for compound 2a confirmed its molecular weight. H
NMR spectrum of compound 2a showed two singlet's, one at
2.36 ppm due to three proton of CH3 on aromatic ring, and
O
O
O
S
N
N
O
O
O
N
H
N
H
HS
OH
O
N
O
N
N
N
N
N
Ph
Ph
Anhydrous ZnCl2
1,4 Dioxane
R
R
3a-f
2a-f
Entry
a
b
c
d
e
f
R
6-CH3
8-CH3
6-OC2H5
8-OCH3
7-OCH3 6-OCH3
Scheme-II

2364 Idrees et al.
Asian J. Chem.
TABLE-2
ANTIBACTERIAL ACTIVITY OF 2a AND 3a AT DIFFERENT CONCENTRATIONS
Zone of inhibition (mm)
Conc. (µg/mL)
Gram-positive: S. aureus
Gram-negative: E. coli
Chloramphenicol
Chloramphenicol
2a
15
12
13
10
16
3a
12
13
12
10
11
2a
15
13
13
12
10
3a
17
17
14
10
10
1000
500
250
125
63
26
30
27
21
18
16
16
17
16
15
Antimicrobial activity:The novel synthesized benzofuran,
quinoline and pyrazole based carbohydrazide and 4-thiazolidi-
none derivatives (2a and 3a), respectively were screened in vitro
for antimicrobial activity at different concentration ranging from
1000 to 63 µg/mL, while remaining compounds 3b-f were studied
at concentration 1000 µg/mL, against bacterial strain S. aureus
and E. coli. According to the screening results, compounds 3a
and 3c showed stronger activity at concentration of 1000 µg/
mL against E. coli. The compound 3a was found to be inactive
against fungal strain A. niger and C. albicans.All the compounds
3a-f were then tested at the same concen-tration 1000 µg/mL.
All the series of compound showed good activities towards selected
bacteria and found to be inactive for fungi under consideration
as shown in Tables 2 and 3.
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The authors are thankful toThe Principal, Government Science
College, Gadchiroli, India for providing the research facilities.
TheauthorsarealsothankfultotheDirector, SAIF, PunjabUniversity,
Chandigarh, India for spectral and elemental analyses. The
authors also thank Guru Nanak College of Science, Ballarpur,
India for providing the facilities of antimicrobial activity.
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The authors declare that there is no conflict of interests
regarding the publication of this article.