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REVIEW ARTICLE
A Review on 1,3-Thiazolidin-4-Ones
Kencha Swathi1*, Dr. M. Sreenivasulu2, T. Hari Narayana Reddy1, Y. Pradeep Kumar1,
G. Mahaboob Basha1
1
ABSTRACT:
1,3-Thiazolidin-4-ones are important group of heterocyclic compounds that are used in the field of medicinal
chemistry. The utility of 1,3-thiazolidin-4-ones as synthons for various biological compounds has given impetus to
these studies. This review aims to review the work reported on the chemistry and biological activities of 1,3thiazolidin-4-ones during the past few years. Since a decade extensive research work is undergoing on the thiazolidine
ring. Researchers have developed number of new compounds related to1,3-thiazolidin-4-ones further they have
screened them for various pharmacological activities to get a molecule with good pharmacological activities and with
least adverse effects. The thiazolidine is not only synthetically important scaffold but also possesses a wide range of
promising biological activities. Some thiazolidine derivatives have better activity than standard drug and could become
a new drug for the market in future. This thiazolidine moiety and its derivatives has shown its importance as antimicrobial, anti-bacterial, anti-tubercular, anti-fungal, anti-inflammatory, analgesic, anti-cancer, anti-proliferative, antiHIV, anti-retroviral,anti-yellowfevervirus,anti-diarrhoeal,anti-arrythmic agent, anti-convulsant, anti-oxidant, antimalarial.
Received on 14.06.2013
Accepted on 15.07.2013
Modified on 24.06.2013
AJRC All right reserved
2
4
N 3
R1
879
N
N
R1
H
N
R2
S
N
N
N
S
R3
CH3
S
O
SH
N
N
SH
N
O
R2
R1
R1
R
R3
S
O
N
8a, 8b, 8c, 8d: R=
R1=H,R2=H, R4=H R5=H.
8a:R3=H, 8b:R3=CF3,8c:R3=Br,8d:R3=Cl.
Haricharan Lal et al6., synthesized 1,2,4-triazole substituted
thiazolidinone and azetidinone derivatives. The synthesized
compounds were evaluated for their antibacterial and antifungal activities by using cup-plate method.Compounds 9
and 10 shown moderate activity.
Shiradkar et al.9, reported a series of N-{4-[(4- amino-5sulphanyl-4H-1, 2, 4-triazol-3-yl) methyl]-1, 3-thiazol-2yl}-2-substituted amide derivatives. These compounds were
tested for their preliminary in-vitro antibacterial activity
against S. aureus, E. coli, P. aeroginosa and S. typhosa and
then were screened for antitubercular activity against M.
tuberculae H37Rv strain by both micro dilution assay
method. Compound [II] and [III] showed best activity. The
compounds showing more than 90% inhibition were
obtained by S-alkylation with acetonitrile. It was noted that
the cyano group did not have any role in increasing the
activity.
880
O2N
N
N
CH2CONH
OH
O
C
NH
H
C
P. Jaya Preethi et al11., synthesized a series of 4thiazolidinones derivatives. These compounds were
screened for anti-tubercular, antibacterial and anti-fungal
activities.
Anti-Tubercular
activity
mycobacterium
tuberculosis and MIC level of the compounds was less than
6.25 g/ml.
H2C
N
HN
N
881
Arun Singh et al17., synthesized a series of3-(2-(5-benzoyl1H-benzo[d][1,2,3]imidazol-1-yl)acetyl)-2-alkylthiazolidin4-one derivatives(5a-d). All the newly synthesized
compounds were evaluated for their antibacterial and
antifungal activities.
R1
N
O
S
N
O
O
R
Ph
N
S
CH2
C
H2
N
R
S
OH
O
C
NH
H
C
S
H2C
R2
R
HO
R1
Cl
CH3
R
[IX]R=H,R1=H,R2=H,R3=H
[X] R=H,R1=CH3,R2=H,R3=H
H
C
S
882
CO O H
O
N
Cl
R
N
S
N
S
O
[XI]
R2
R3
SH
O
R
O
N
IIIa: R=4-SCH3,R2=4-OCH3,R3=H.
O
O
O
883
C18H37
N
H
VI
O
C18H37
N
H
VII
O
O
C18H37
N
H
CH3
VIII
R=
25
N
CH3
[XIV]
The anti-HIV activity of several series of 2, 3- diaryl-1, 3thiazolidin-4-ones [XV] has been studied by Chavan, Y.B.
et al.,28,29,30 Which are reported as a new family of antiviral
agents acting as NNRTIs with minimal cytotoxicity.
R1
Ar
N
Me
N
H
NO2
884
Me
MeO
41
Me
Me
42
N
Me
Me
F
Cl
(40)
C2H5
H3CO
XVII
O
N
S
C2H5O
C2H5
H3CO
NC
XVIII
39
Wilson Cunico et al., have been synthesized Several 5-[(2phenyl-4-oxo-thiazolidin-3-yl) amino]-2-oxo-thio barbituric
Thiazolidinone with anti-diarrhoeal activity
acids derivatives [XIX and XX]34 and 3-({4-[2alkylphenyl)-4- oxo-1,3-thiazolidin-3-yl]-1,3,4-thiadiazol6. ANTI- ARRYTHMIC ACTIVITY
2-yl}methylamino)-2-methyl-6monosubstituted-quinazolinAtrial flutter and atrial fibrillation are the most common
4(3H)-one derivatives [XXI]35 and screened in-vivo for their
cardiac arrhythmias and they are associated with an increase
anticonvulsant activity.
in heart failure, stroke, and mortality. Blockade of the
Kv1.5 ion channel is potentially atrial-selective avenue for
O
the treatment of atrial fibrillation and atrial flutter. Jackson
O
et al.,32 described the synthesis and biological evaluation of
N
S
HN
N
thiazolidinone-based blockers of Kv1.5. The 3,4-dimethyl
H
derivatives 41 (IC50 = 0.069M) and 42 (IC50 = 0.270M)
S
N
O
were the most potent compounds of this series .
H
R
[X IX ] R = p -O C H 3
[X X ] R = m -O C H 3 ,p - O H
885
O
N
Me
H3C
C6H5
HN
N
Br
N
N
N
H
N
N+
N
N
ON
O
XXI
(XXII)
OMe
OH
P. Jaya Preethi et al.,36 synthesized a series of 4thiazolidinones and 2-azetidinone derivatives by refluxing
Schiff bases with different aromatic aldehydes. Schiff bases
were synthesized by reaction of nicotinamide with
hydrazine hydrate. The chemical structures of the
synthesized compounds were confirmed by means of IR,
1H-NMR, mass spectroscopy and elemental analysis.
Compound IIIa, IIId, IVa and IVd exhibited good Anticonvulsant activity.
Arun M. Isloor et al.,39Synthesised a new series of 2-(3substituted-1H-pyrazol-4-yl)-3-(3-substituted-5-sulfanyl1,2,4-triazol-4-yl)-1,3-thiazolidin-4-one (4ao) by cyclocondensation reaction of 5-substituted-4-[(3-substituted-1Hpyrazol-4ylmethylidene)amino]-2H-1,2,4-triazole-3-thione
(3ao) and thioglycolic acid. The synthesized compounds
were screened for anti-oxidant activity. In vitro antioxidant
studies like DPPH and ABTS-free radical scavenging
assays-indicated moderate activity of thiazolidin-4-ones.
N
N
R
SH
O
N
NH
N
S
HN
R1
N
S
HN
HN
S
Cl
CH
Cl
HN
Cl
2(a-f)
XVI
CONCLUSION:
7. ANTIOXIDANT ACTIVITY
Shih et al.,38 synthesized a series of sydnonyl substituted
thiazolidinone and thiazoline derivatives and evaluated for
their antioxidant activity. The antioxidant activity of
compound [XXII] have been found to exhibit the significant
DPPH (1, 1-diphenyl-2- picrylhydrazyl) radical scavenging
activity, comparable to that of vitamin E.
886
19.
FUTURE ASPECT:
20
21
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