Devprakash et al.

/ Journal of Pharmacy Research 2011,4(7),2436-2440

Review Article Available online through
ISSN: 0974-6943 www.jpronline.info
A complete review of thiazolidine-4-ones.
Devprakash1 and Udaykumar A Bhoi. *1
1
Department of Pharmaceutical Chemistry, Bharathi College of Pharmacy, Bharathinagara-571422, Karnataka, India.
Received on: 12-04-2011; Revised on: 18-05-2011; Accepted on:21-06-2011

ABSTRACT
Thiazolidine-4-ones containing thiazole moiety, it had been synthesized by 6-amino Coumarin, Isatin, Primary amines and aromatic aldehydes. Thiazolidine-
4-ones has been considered as a magic moiety because it posses almost all types of biological activities such as Antifungal, Antitubercular, Antimicrobial,
Antioxidant, Antibacterial, Cytotoxic, Anti-inflammatory, Analgesic, Anti YFV (yellow fever virus) activities. Present article is sincere attempt to review of
chemistry, different methods of synthesis, and pharmacological uses of thiazolidine-4-ones.

Key words: Thiazolidine-4-one, Spiro-thiazolidinone, Schiff bases, Biological activity.

INTRODUCTION
The chemistry of heterocyclic compounds is as logical as that of aliphatic or • Thiazolidine-4-ones having 2,4-dimethyl amino phenyl at second position
aromatic compounds. Their study is of great interest both from the theoretical shows good antitubercular activity in all the species3.
as well as practical importance. Various compounds such as alkaloids, essential • Un-substituted phenyl group at the fourth position of thiazolidine-4-one in-
amino acids, vitamins, hemoglobin, hormones, large number of synthetic drugs creases antioxidant activity.
and dyes contain heterocyclic ring systems. There are large number of synthetic • The presence of para-fluorophenyl substituent decreased the cytotoxicity of
thiazolidin-4-one derivatives against DLA cells.
heterocyclic compounds, like pyrrole, pyrrolidine, furon, thiophene, piperi-
• The un-substituted phenyl ring at third position shows less activity against
dine, pyridine and thiazole having important application & many are important gram negative strains and moderately effective against gram positive8.
intermediates in synthesis. Heterocycles containing sulphur and nitrogen atoms • The nitro group at meta and para position of the aryl ring respectively, possess
in the core structure, it shows number of pharmacologically and biologically stronger antibacterial activity.
active compounds. • Electron withdrawing moiety shows less activity compared to electron
O 4 3 donating group eg. OCH3 and NMe9.
Thiazolidine-4-ones are usually solids, often melting with
N
decomposition but the attachment of an alkyl group to the
nitrogen lowers the melting point. Thiazolidine-4-ones 2 Different methods for synthesis of Thiazolidine-4-ones:
5
are derivatives of thiazolidine with carbonyl group at the S
fourth position. The carbonyl group of thiazolidine-4-ones 1 Scheme-1:
is highly un-reactive. Thiazolidine-4-ones are the deriva- Jubie, et al3., synthesized series of 3-(methoxy phenyl)-2-aryl thiazolidin-4-one
tives, which belongs to important groups of heterocyclic Structure of by the reaction with schiff bases. The Schiff bases were synthesized by conden-
compounds containing sulfur and nitrogen in a five mem- Thiazolidine-4- sation of p-methoxy aniline with different substituted aromatic aldehydes. The
ber ring12. one obtained Schiff bases were subjected to condensation with mercaptoacetic acid
to give the corresponding 4-thiazolidinones. The yield was found to be 42-62 %.
The nucleus is also known as a wonder nucleus, because it shows different types
of biological activities12. Thiazolidine-4-one substituted moieties have received
considerable attention during last two decades as they are gifted with variety of Ar
Ar-CHO/EtOH SHCH2COOH NH2
activities and have wide range of therapeutics properties. Thiazolidine-4-ones OMe NH2 OMe N OMe N
and its derivatives offer enormous scope in the field of medicinal chemistry. S
O
1 2 3
Thiazolidine-4-ones are important compounds due to their broad range of bio-
logical activities and pharmacological properties i.e. Antifungal(2,12), Antioxi-
dant(3), Cytotoxic(3), Anti-inflammatory(4), Analgesic(4), Anti YFV (yellow fever Substituents:
virus) activity(5) , Antitubercular (10,16) , Antimicrobial (2,4,10,11,18,20,21) , Antibacte-
rial(9,10,12,15,20) , Thiazolidine-4-one derivatives possess different pharmacological
and biological activities. Antimicrobial activity is the most potent activity of Cl
thiazolidine-4-one. Antibacterial activity is strongly dependent on the nature of
Cl N
substituent at C-2 & N-3 position (12).
3a 3b 3c 3g
SAR of Thiazolidine-4-ones:
Cl Cl O
• The thiazolidin-4-ones bearing 2,4-dichlorophenyl group hydroxyl methoxy
phenyl 4-chlorophenyl group and dimethylamino group at second position have
Cl OMe OH
showed good antitubercular activity.
3d 3e 3f 3i

* Corresponding author.
Devprakash Scheme-2:
1
Department of Pharmaceutical Chemistry, Gurupadayya et al 4 ., synthesized various 7-chloro-6-fluro-2-arylidenyl
Bharathi College of Pharmacy, aminobenzo (1,3)(2a-2h) by the condensation of 7-chloro-6-fluro-2-
Bharathinagara-571422, Karnataka, India. aminobenzo(1,3) thiazole(1) with different aromatic aldehydes. Cyclization of
Tel.: + 91-9590280064 Schiff base with thioglycolic acid produced 3-(7-chloro-6-fluro-benzothiazol-2-
E-mail: bhoi.uady@gmail.com
yl)-2-substituted-arylthiazolidin-4-ones (4a-h).

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 Devprakash et al. / Journal of Pharmacy Research 2011,4(7),2436-2440
ence of toluene. The synthesis of 2-[3-nitrophenyl-1-(pyridin-4-ylcarbonyl)-
1H-pyrazol-4-yl]-3-substituted-1,3-thiazolidin-4-one 3a-j was carried out in
EtOH
N N three steps, first by the condensation of isoniazid with 4- nitroacetophenone in
+ R-CHO
the presence of glacial acetic acid to give N’-[1-(4-nitrophenyl) ethylidene]
F S NH2 benzohydrazide, secondly Vilsmeier Haack complex was treated with it to give
S N CH-R
Cl 3-(4-nitrophenyl)-1-(pyridin-4-yl carbonyl)-1Hpyrazole-4-carbaldehyde, which
2 a-h
1
on treatment with different substituted aromatic amines and thioglycolic acid in
RCH2COCl the presence of toluene afforded the title compound. Cyclization of 3-(4-
CH2SHCOOH
nitrophenyl)-1-(pyridin-4-yl-carbonyl)-1H-pyrazole-4-carbaldehyde carried out
by the reaction with thioglycolic acid.
N
O
R N O
+ CH3
S N N
F H3C O
Cl S N R O N +
N CONHNH
2
CONHN N
O R' Cl CH3COOH
S O
2-3 min 1
3 a-x O
4 a-h 3-4 min DMF/ POCl
3

Scheme-3: N NH N N O SHCH2COOH
Sriram et al 5 ., prepared several 1,3-thaizolidin-4-ones bearing variously N
+
N NH N N O
unsubstituted diaryl ring at C-2 and N-3 positions and evaluated them for their R-NH2, Toluene +
O N
12 min
anti-YFV activity. The synthesis of the 2,3-diaryl-1,3-thiazolidin-4-ones (DS1- O
15) was done by reacting substituted benzaldehyde with equimolar amount of an R N S 2
appropriate substituted aromatic amine in the presence of an excess of mercap- 3 a-j
toacetic acid in toluene utilizing microwave irradiation. O

R
3a= C6H5; 3b= 4- C6H4NO2; 3c= 4- C6H4Cl; 3d= 4- C6H7O; 3e= 4- C6H7; 3f= 4-
R
H C6H7O; 3g= 4- C6H5O2; 3h= 3- C6H4NO2; 3i= 4- C6H4F; 3j= 4- C6H4Br.
Toluene Ar
Ar NH2 + HS COOH + N
O MWI, 6-8 min Shceme-6:
80% intencity S Ketan et al11., synthesized new series of compounds namely 3-chloro-4-(2'’,4'’-
O dichlorophenyl)-4-methyl-1-(substituted-1',3'-benzothiazol-2’yl)-azetidin-2-
DS 1-15 ones and 2-(2',4'-dichlorophenyl)-2,5-dimethyl-3-(substituted-1',3'-benzothiazol-
2'-yl)-1,3-thiazolidin-4-ones by the reaction of schiff base derivatives with
chloroacetyl chloride in presence of triethylamine thiolactic acid respectively.
Compound Ar R
H O
N N
NH2+
Microwave
2-3 min
R Cl
N C Cl
S CH3 Conventional
5-6 hrs S CH3
Cl
Cl

ClCH2COCl Microwave
6-7 min
TEA Microwave 6-7 min
SHCH(CH
3)COOH
Conventional
15-16 hrs
15-16 hrs
Conventional

Scheme-4:
O
Ranjana et al8., synthesized 2-Isonicotinoylhydrazido-1,3-thiazolidin-4-one by Cl O CH3
reaction of Isonicotinoyl thiosemicarbazide with chloroacetic acid in absolute N N
R R
alcohol and anhydrous sodium acetate. N Cl N S
S S Cl
O O CH3
NH 2 NH NH 2 CH3
NH 4 SCN, 1N HCl Cl
NH NH Cl
S
N N

ClCH 2 COOH, AcONa

EtOH

O H
N N
O
NH
N S

a-h

Ar (a-h) = 4-OCH3.C 6H 4; 4-Cl.C 6H 4; 3,4,5-OCH 3.C 6 H2; 3-NO2.C 6H 4; 4-NO2.C 6H 4; 4- Scheme-7:

(CH3)2NH.C6H4; C6H5; C4H3O (2-furyl).
Scheme-5:
Visagaperumal et al10., synthesized some new 3- substituted-1, 3-thiazolidine-4-
ones by the reaction of 3-(4-nitrophenyl)-1-(pyridin-4-ylcarbonyl)-1H-
pyrazole-4-carbaldehyde and different substituted aromatic amines in the pres-
Liu et al 12 ., synthesized five derivatives of 2-imino-3-(4-arylthiazol-2-yl)-
thiazolidin-4-ones and series of their 5-arylidene derivatives, were tested for
antifungal activity against seven agricultural fungi. The thiazolidinones (1) was
obtained by crystalisation from ethanol and melting point was found to be 173-
175 0 c.

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 Devprakash et al. / Journal of Pharmacy Research 2011,4(7),2436-2440
Method-1 Method-2 Scheme-10:
S
Vandana Tiwari et al15., used Zeolite 5A° for the synthesis of 2-(2-chloroquinoline-
O O S
+ + 3-yl)-3-substituted phenyl thiazolidin-4-ones starting from N-aryl-2-
Ar C H3 H2N N H2 H 2N NH2
Ar CH 2 X chloroquinolin-3-yl-azomethine and thioglycolic acid under microwave irradia-
tion.
1. I 2 2 . NH 3 .H 2 o X=Cl, Br, I R1 R2
R2 R1
O Ar CHO
O
N C N R3
Ar
Cl
Cl Cl + R3 NH2 MWI, 200W
N NH
S N Cl 20-30 sec
R4 R5 R5 R4
N H2 4 N
S
3 3(a-i)
KSCN
Ar
O SHCH2COOH/Zeolite5A
N ArCHO
Ar
O MWI, 200W, 30-60 sec
N CHAr N
S
S N
S O R1
HN R2
S
2 S
HN
1 C N R3
2a= Ar= C6H5, Ar´= o-O2N C6H4; 2b= C6H5, Ar´= m-O2N C6H4; 2c= C6H5, Ar´= o-Cl C6H4
2d= p-Cl C6H4, Ar´= o-O2N C6H4; 2e= p-Cl C6H4, Ar´= m-O2N C6H4
R5 R4
N
Scheme-8:
4(a-i)
Rajiv et al13., synthesized some new N1-[2'-{2-substituted-phenyl-5-substituted-
benzylidene-1,3-thiazolidine-4-one}-5'-methylene-1',3',4'-thiadiazole] -2-me- R1 R2 R3 R4 R5
thyl-benzimidazoles, 6(a-n) conventional and green approach methods in terms
2a,3a,4a -H -H -H -H -H
to yield and reaction time along with antimicrobial activity against Bacillus 2b,3b,4b -Cl -H -H -H -H
subtilis, Escherichia coli, Klebsiella pneumonia and Streptococcus aureus bac- 2c,3c,4c -H -H -Cl -H -H
teria and Aspergillus niger, Aspergillus flavus, Fusarium oxisporium and Tricho- 2d,3d,4d -OCH3 –H -H -H -H
derma viride fungi in vitro at 50 and 100 ppm concentrations. 2e,3e,4e -H -OCH3 -OCH3 -H -H
N ClCH2COOC2H5 N NH2NHCSNH2 N
CH3
Scheme-11:
CH3 CH3
N N N
Raga Basawaraj et al18., synthesized 3-{[(1E)-1-(5-chloro-3-methyl-1-benzofu-
H ran-2-yl) ethylidine]amino}-2-substituted phenyl-1,3-thiazolidin-4-one deriva-
CH2COOC2H5 2 CH2CONHNHCSNH2
1 tives by reaction of substituted benzaldehyde[1-(5,-chloro-3'-methyl-1'-benzo-
N H2SO4/NH3 furan-2'-ethylidine] hydrazones with thioglycolic acid in the oil-bath at 115-
CH3
Ar1COH / CH3COOH
N 120 oC for 12 hrs.
N N N
CH3
SHCH2COOH/ ZnCl N N N Cl CH3
S N CHAr1 COCH3 Cl CH3
4 a-n 3 ClCH2COOH3 / Dry Acetone
N S NH2
N
CH3 Anhy K2CO3
CH3 OH O O
N N N
N N N Ar2CHO/ C2H5ONa
Ar1
Ar1
S N
S N
5a-n S
NH2-NH2 / EtOH / HCl
S 6 a-n
O
O CH3
Ar2HC Cl CH3
6b= Ar1=2-ClC6H4, Ar2= 2-Cl C6H4; 6c= Ar1=3-Cl C6H4, Ar2=3-Cl C6H4; Cl CH3
CH3
6d= Ar1=4-Cl C6H4, Ar2=4-Cl C6H4; 6e= Ar1=2-Br C6H4, Ar2=2-Br C6H4; R-CHO / EtOH
6f= Ar1=3-Br C6H4, Ar2=3-Br C6H4; 6g= Ar1=4-Br C6H4, Ar2=4-Br C6H4; O N
Scheme-9: CH N O N
R
Desai et al 14 ., synthesized various 2-(4-chlorophenyl)-N-(4-oxo-2- H2N
arylthiazolidin-3-yl) acetamides by the cyclization of (Z)-N-arylidene-2- SHCH2COOH
ClCH2COCl / Dioxane
(chlorophenyl)-acetohydrazides 1 and N-(l-aza-2-arylvinyl)(4-[5-oxo-2-phe-
nyl-4-phenylmethelene)(2-midazolinyl)phenyl)caroxamides in the presence of
thioglycolic acid and 1:4 dioxane. CH 3 Cl CH3
CH3
HO O Cl CH3 R
CH3
O CH 3 CH 2 OH O NH 2 -NH 2
R
Cl H 2 SO 4 Cl CH 3 CH 2 OH O N N S
O N
H3C N
H 2N NH Ar O Cl O
CH 3 CH 2 OH NH
O Cl a= C6H5; b= C6H4OH(p); c= C6H4Cl(p); d= C6H4OCH3(p)
Cl ArCHO
1

(C 2 H 5 ) 3 N
Biological activity:
1: 4 DIOXANE Antibacterial activity:
SHCH 2 COOH
ClCOCH 2 Cl 1: 4 DIOXANE
1) Vinita et al 9., have been screened compounds 5a-i for their antimicrobial
O
NH Ar O activity by cup plate method and have found to exhibit significant activity
N NH Ar against B.Subtilis, E.coli at different concentration (50 and 100 µg/ml) using
Cl N
S Cl DMSO as solvent. The results of antibacterial activity shows that compound 5f
O
O Cl
and 5i have good activity compared to the standard.
2 3

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 Devprakash et al. / Journal of Pharmacy Research 2011,4(7),2436-2440
O R2
O Fungicidal activity:
O 1) Gowri Chandra Sekhar et al2., synthesized compounds most of them were
found to possess moderate activity against tested fungi. Compounds 3d and 3h
N were found to be most active against Aspergillus flavus and Candida albican
R1 respectively. The antifungal activities of test compounds were compared with
S standard Salicylic acid (20 - 30 mm) and Clotrimazole (25 - 30 mm).
HN
R
N CH3
5f= R1=H, R2= CH3, R=OCH3; 5i= R1=R2= CH3, R=Cl

2) Desai et al14., screened antibacterial activity of compounds (2a-2g,3a-3i,7a-

7j and 8a-8c) against gram (+) ve and gram (-) ve bacteria i.e. S.aureus and N NH
E.coli by cup plate method.5And these compounds showed good antibacterial O N Ar
activity compare to the standard drug ciprofloxacin.
O
3 a-h S
NH
Ar
3a=Ar= C6H5, 3b=Ar= m-NO2-C 6H4,
Cl N 3c=Ar= p-NO2-C6H4, 3d=Ar p-CH3- C6H4,
3e=Ar= p-OCH3-C6H4, 3f=Ar= o-OH- C6H4,
O S
2) Hui-Ling et al12., tested antifungal activity against seven agricultural fungi,
P.ostreatus, A.niger, P.aphanidermatum, G.graminis, F graminearum, P.oryzae,
2a= (Ar=4-CH3-), 2b=(2-OH-), 2C=(2-OH-5-Br-)
B.cinerea ,the result shows that the new compounds 1d & 1e have higher
3) Aamer et al16., carried out In vitro evaluation of antibacterial activity by disk fungicidal activity.
diffusion method (Kirby-Bauer method) against different bacterial strains. All Ar H
the compounds 2a-2i exhibited promising inhibitory activity against the four O
bacterial strains compared to standard drugs at the tested concentrations. Com-
N
pounds 2h and 2i are having better activity. Activity tested by comparing with
standard drug like penicillin, tetracycline and metronidazole. N
S
S S
N
R1 HN
N
1d=[Ar=2,4-(Cl)2-5-FC6H2], 1e=[2,4-(Cl)C6H3]
O
Anti-YFV activity:
Drmarajan et al5., evaluated all compounds compound were also evaluated for
their inhibitory effects on the replication of YFV in green monkey kidney
R2 (Vero) cells (ATCC CCL81), by means of a cytopathic effect reduction assay
[12]. The antiviral activity of the compounds was expressed as the effective
2a; R1= R2 =H 2a= 6.7 (mmol 103 per ml) concentration required to inhibiting the viral cytopathic effect by 50% (EC50).
2b; R1= H, R2=2-Me 2b= 6.4 (mmol 103 per ml) The minimum cytotoxic concentration was expressed as CC50, the concentra-
2c; R1= H, R2=3-Cl 2c =6.0 (mmol 103 per ml) tion required to reduce cell growth by 50%. Six compounds (DS1-3, DS6-7 and
2d; R1= 3-Me, R2=H 2d =6.4(mmol 103 per ml) DS14) were found to prevent the YFV infection of the cells at concentrations
2e; R1= 2-Cl, R2=2-OMe 2e =5.5 (mmol 103 per ml) that had no effect on cell growth. Four compounds (DS1-3 and DS-14) were
2f; R1= 3-Cl, R2=H 2f =6.0 (mmol 103 per ml) found to be more effective than ribaviri (EC50 values of 28.0 µm). The com-
2g; R1= 2-Br, R2=2-OMe 2g =4.9 (mmol 103 per ml) pound DS-1 emerged as the most potent anti-YFV agent with EC50 of 6.9 µm
2h; R1= 3-Cl, R2=3-Me 2h= 5.8(mmol 103 per ml) and CC50 more than 100 µm.
2i; R1= 3-Me, R2=3-Cl 2i =5.8 (mmol 103 per ml)
2j; R1= 3-Me, R2=2-OMe 2j= 5.9(mmol 103 per ml) R
Antitubercular activity:
Sriram et al5., screened synthesized compounds for the antitubercular activity
Ar
against mycobacterium tuberculosis H37Rv using resazurin microplate assay 25
(REMA) at the concentration of 1, 10, 50µg/ml. All the compounds have given N
mild activity at 50µg/ml especially 3d have given a good activity at 1 and 10 µg/
ml. S
O
N NH N N O
+ DS1= Ar= 4-F-C6H4, R=4-Cl, DS2= Ar=4-F-C6H4,R=2-Cl,
N DS3= Ar=4-F-C 6H4, R=3-NO2, DS6= Ar=2,6-(CH3)2-C 6H3, R= 4-NO2, DS7=
O Ar=2,6-(CH3)2C6H3, R=4-OH,DS15= Ar=3-CH3-2- C5H4N-, R=4-Cl,
DISCUSSION:
R N S The literatures survey shows that thiazolidine-4-ones has diverse biological
3 a-j potential, and the easy synthetic procedures for synthesis have taken attention
O of the chemists, pharmacologists and researchers.
3a=R= C6H5, 3b=R= 4-C6H4NO2, 3c=R= 4-C6H4Cl,
Thiazolidine-4-ones can be synthesized by using coumarin derivatives, isatin
3d=R= 4-C7H7O, 3e=R= 4-C7H7, 3f=R= 4-C8H7O,
derivatives, primary and secondary amines. Cyclization of compounds can be
3g=R= 4-C7H5O2, 3h=R= 3-C6H4NO2, 3i=R= 4-C6H4F,
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 Devprakash et al. / Journal of Pharmacy Research 2011,4(7),2436-2440
carried out by using thioglycolic acid and chloroacetyl chloride. By
heterocyclization of Quinoline-imines with thioglycolic acid using zeolite 5A°
under microwaves afforded 2-(2-chloroquinoline-3-yl)-3-substituted phenyl
thiazolidin-4-one. Microwave irradiation process is fastest synthesis procedure
for thiazolidine-4-ones. Substitution is possible at 2, 3 and 5 position of
thiazolidine-4-ones.
Thiazolidin-4-one have a broad spectrum of pharmacological properties i.e.
Antifungal, Anti-tubercular, Antimicrobial, Antioxidant, Cytotoxic, Anti-in-
flammatory, Analgesic, Anti YFV (yellow fever virus) activities. Antimicrobial
is the most potent activity of the thiazolidine-4-ones. Anticancer and anti HIV
are most encouraging activities of thiazolidin-4-ones for the researchers for the
development of newer anticancer and anti HIV agents, which is requirement of
today medicinal field.
ACKNOWLEDGMENT:
We are thankful to the Dr. T. Tamizmani, Principal, Bharathi College of Phar-
macy. for providing library facilities.
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