Mashrai et al., Med chem (Los Angeles) 2016, 6:4 DOI: 10.4172/2161-0444.1000358

Review Article

Medicinal chemistry

ISSN: 2161-0444

Medicinal chemistryOpen Access

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 280

Strategies for the Synthesis of Thiazolidinone HeterocyclesAshraf Mashrai1,2, Ayaz Mahmood Dar1,3*, Shafia Mir3 and Shamsuzzaman1

1Department of Chemistry, Aligarh Muslim University, Aligarh-202 002, Uttar Pradesh, India2Department of Pharmacy, University of Science and Technology, Sana'a, Yemen3Department of Chemistry, Government Degree College Kulgam, University of Kashmir, Jammu and Kashmir, India

*Corresponding author: Ayaz Mahmood Dar, Department of Chemistry, Aligarh Muslim University, Aligarh-202 002, Uttar Pradesh, India, Tel: +91928699027; E-mail:ayazchem09@gmail.com

Received April 14, 2016; Accepted April 26, 2016; Published April 30, 2016

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Copyright: © 2016 Mashrai A, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

Keywords: Schiff ’s bases; Mercaptoacetic acid; Condensation; Heterocycles

ThiazolidinonesThiazolidinones and their derivatives display a large variety of activities such as antibiotic, diuretic, organoleptic, tuberculostatic, antileukaemic

and antiparasitical [1,2]. As far as literature is concerned, little is known about thiazolidinones and their bioactivities. Thiazolidinones (1) are classified as doubly unsaturated five membered heterocyclic compounds contain one nitrogen, one sulphur and three carbon atoms including a carbonyl group.

HNS

O (1)

Moawad et al. reported that reaction of Schiff base (3) with mercaptoacetic acid in dry benzene afforded thiazolidinone (4). Schiff base (3) was obtained by the condensation of, 3,4-xylene sulphonate ester of p-hydroxy benzaldehyde (2) with p-aminobenzoic acid [3].

CH3

CH3

SO3

p-Amino benzoic acidCH3

CH3

SO3 CH N COOHCHO

(2) (3)

Thioglycolic acidCH3

CH3

SO3 CH N COOHS

O(4)

Gursoy et al. prepared new compounds (5) and (6) incorporating the quinazoline moiety [4].

AbstractThiazolidinones is the special class of heterocyclic compounds with a broad spectrum of biological activities

such as anti-inflammatory, antiproliferative, antihistaminic, anti-HIV, hypnotic, anaesthetic, antifungal, anthelmintic and antiviral agents as well as CNS stimulants. Therefore researchers have synthesized these condensed heterocycles through different complex pathways as target structures for biological studies. This review focuses on the various strategies followed for the convenient synthesis of thiazolidinone based heterocyclic derivatives. The steps included condensation followed by cyclization of Schiff’s bases, either in a step-wise manner or in one pot under different conditions. Mercaptoacetic acid, thiolactic acid, chloroacetyl chloride, potassium thiocyanate, ethylchloro acetate and ammonium thiocyanate are the most common reagents used for the synthesis thiazolidinone appended on different heterocyclic skeletons.

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 281

N

N

OC6H5

SCH2CONHNHCS

NH R N

N

OC6H5

SHCH2COHNHNS

N OR1

(5) (6)

Ansari et al. synthesized 4-thiazolidinones (8, 9) starting form chalcone (7), by two different route as shown in the following scheme [5].

CO

HC CH

(7)

CO

H2C CHC

H2C CH

HSCH2COOHHSCH2COOH

HSCH2COOH

(NH4)2CO3

(NH4)2CO3

SCOOH

COOHNH

O

S

(8) (9)

El-masry et al. reported that condensation of compound (10) with aromatic and heterocyclic aldehydes in absolute ethanol afforded the corresponding Schiff ’s bases (11). The cyclocondensation of some substituted Schiff ’s bases with thioglycolic acid and thiolactic acid afforded the corresponding thiazolidinone (12) and (13) [6].

N

N

CH2CH2CONHNH2

RCHON

N

CH2CH2CONHN CHR

(10) (11)

N

N

CH2CH2CONHNSO

R

CH3

Thioglycolic acid Thiolactic acid

N

N

CH2CH2CONHNSO

R

(12) (13)

Cl

NO2

S

=R

Cl

NO2

S

=R

Anthonsen et al. synthesized 2-imino-3-(4-arylthizol-2-yl)-thiazolidin-4-ones (16) via the key intermediates, 2-amino-4-arylthiazoles (14) which were reacted with chloroacetyl chloride to produce the corresponding 2-chloro-acetamido-4-arylthiazoles (15). The latter was treated with potassium thiocyanate in refluxing acetone to afford the product (16) [7].

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 282

ArCO

CH3

+H2N C

O

NH2I2

NH3 H2O

N

S NH2

Ar ClCOCH2Cl N

S NH

ArC Cl

O

ArCO

CH2X+ NH2

CO

NH2

X = Cl, Br, I

KSCN N

S N

Ar

S

O

HN

(14) (15) (16)

Ocal et al. synthesized substituted 4-thiazolidinones (18) by the reaction of mercaptoacids aldimines (19) which were obtained by the condensation of pyrrole-2-carbaldehyde with different aromatic amines [8].

XNHCNH

XNHCNH

RCHCOOHSH

S O

R(17) (18)

R= H, CH3

Abbady et al. obtained 4-acetylthiosemicarbazone-4-acetyl diphenyl sulphone (19) and 4-acetylthiosemicarbazone-4-acetyldiphenyl sulphide (20) which on further reaction with ethylchloroacetate in the presence of fused AcONa gave 4-(4"-thizolidinone-2"-acetylazino)-4'-acetyldiphenylsulphone (21) and 4-(4"-thizolidinone-2"-acetylazino)-4'-acetyldiphenyl sulphide (22), respectively [9].

CO

H3C S

O

O

C NCH3

NH CS

NH2

CO

H3C S C NCH3

NH CS

NH2

CO

H3C X C NCH3

N

S

HN

O

Ethyl chloroacetate

Ethyl chloroacetate

AcONa

AcONa

(19)

(20)

(21), (22)

Parekh et al. prepared that substituted Schiff ’s bases (24) by the treatment of 2-amino-4-(α-methoxyiminocarbomethoxymethyl)-thiazole (23) with different aromatic mercaptopropionic acid in dry benzene furnished desired thiazolidinones of type (25) and (26) respectively. The products were evaluated for their in vitro growth inhibiting activity against several microbes. Some of them showed significant anti-tubercular and antifungal activity [10].

S

NH2N

NO

CH3

OO

CH3

(23)

S

NN

NO

CH3

OO

CH3

R(24)

S

NN

NO

CH3

OO

CH3

S

O

RH3C

S

NN

NO

CH3

OO

CH3

S

O

R

(25)(26)

HSCH2COOH

HSCHCOOHCH3

R=Ar

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 283

Monforte et al. reported the synthesis of 2,3-diaryl-1,3-thiazoldin-4-ones (29) by reacting an aromatic aldehyde (28) with an equimolar amount of (hetero) aromatic amine (27) in the presence of an excess of mercaptoacetic acid. The microwave-irradiation dramatically shortened the reaction times, affording the desired products in high yields [11].

Y

X

R1

R2

+

R4

R5

R3

CO

H

R4

R5

R3

NS

X

Y

R1

R2

O

HSCH2COOH

(27) (28) (29)

X=CH, N R1=Me, OMe, Br

Y=CH, N R2=H, Me R4=H, Me R3=Cl, F R5=Cl, F

Terzioglu et al. synthesized the target compound, 2-(3-ethyl-4(3H)-quainazolinone-2-ylmercaptoacetylhydrazono)-3-alkyl/aryl-5-methyl-4-thiazolidinones (31) and 2-arylimino-3-(3-ethyl-4(3H)-quinazolinone-2-ylmercaptoacetylamino)-5-methyl-4-thiazolidinones (32) by the cyclization of 3-ethyl-4(3H)-quinazolinone-2-ylmercaptoacetyl)-4-alkyl/arythiosemicrabazides (30) with ethyl 2-bromopropionate in presence of anhydrous sodium acetate in absolute ethanol [12].

CH3BrCHCOOEtCH3COONaabs.ethanol

N

N

O

SHN

NO

N

N

O

SHN

NO

N

N

O

SHN

NH

NH

RO

S

S

NR

OSN

R

O

(30)

(31) (32)R=CH3, C6H11

Altintas et al. synthesized by refluxing of 4-carbethoxymethyl-2-[(α-chloropropoinyl/ α-bromobutyryl/ α-chloro-(phenyl)acetyl)amino] thiazoles (34) with ammonium thiocyanate to obtain 4-thiazolidinone (34). 5-(N,N-disubstitutedaminomethyl-2-[(4-carbethoxymethylthiaxol-2-yl)imino] 4-thiazolidinones (34) was evaluated as antibacterial and antifungal activities [13].

N

S NH2

C2H5OCOH2C

- HX

RCHXCOXN

S NHCOCHX

C2H5OCOH2CR

(33) (34)

NH4SCN

CH2O+ R1H

N

S N

C2H5OCOH2C

S

HN O

RCH2R1

(35)

R=CH3, C2H5, C6H5 X= Cl, Br

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

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Sriram et al. reproted that the synthesis of the 2,3-diaryl-1, 3-thiazolidin-4-ones (38) was acomplished by reacting substituted benzaldehyde (37) with equimolar amount of an appropriate substituted aromatic amine (36) in the presence of an excess of mercaptoacetic acid in toluene under microwave irradiation. Unlike the conventional methods (reaction time 48 h and yeilds of 30-70%), microwave-assisted reactions were very facile (6-8 min.) and provided very good yields (64-82%) [14].

Ar-NH2 +

OH

HSCH2COOH

TolueneMWI

R R

N

SO

Ar

(36) (37) (38)

[Ar=4-F-C6H4-, R=4-Cl, 2-Cl]

Arya et al. prepared spiro[indole-thiazolidines] (41) by the multicomponent condensation between indole-2,3-done (39), amines (40) and marcaptoacetic acid using montmorllonite KSF as solid support in 85-90% yield in 4-5 min under MW reaction conditions [15].

NH

O

O +Y

NH2

MW

KSFHSCH2COOH

NH

NYO

X

S O

(39) (40) (41)

X=H, 5-Cl, 5-CH3 Y=OCH3,

Desai et al. synthesized 4-thiazolidinones (43) in a good yields from the heterocyclization reaction of 2-(benzothiazol-2-ylthio)-N'-benzylideneacetohydrazide (42) with mercaptoacetic acid in DMF in the presence of catalytic amount of anhydrous ZnCl2 under microwave irradiation and compared with conventional methods [16].

S

NSCH2CONHN CH

(42)

S

NSCH2CONHN CH

SO

R

SHCH2COOH

(43) R=4-NO2, CH3

Nagarajan et al. synthesized E-thiazolidinone (46) by the cyclization of acetylene dicarboxylic ester (44) with thiocarbamoyl derivatives (45) [17].

CO2MeCO2Me

+ RNH CS

NHR NO

RN HCO2CH3

R

(44) (45) (46)

Sahu et al. reported that condensation of substituted benzaldehydes (47) with primary aryl amines (48) gave a series of Schiff bases (49) which, on reaction with mercaptoacetic acid, resulted in the formation of the corresponding 4-thiazoldinones (50) [18].

CHOR

+ Ar NH2EtOH

CHR

N Ar

(47) (48) (49)

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 285

HSCH2COOH

CHR

N ArS

O

(50)

Ar=4-NO2, Phenyl, 4-Cl and Naphthyl R=2-OH, 4-N(CH3)2, 4-NO2, 4-Cl and 4-OCH3

Desai and Shah synthesized of 2-(substituted phenyl)-3-[4-(2,4-dichloro-5-fluorophenyl)-6-(2-thienyl)pyrimidine-2-yl-ureido] 5H/ methyl/carboxymethyl-4-thiazolidinones (54). It starts with compound (51) and employing the following reaction scheme [19].

F

ClCl

N N

S

NH2

F

ClCl

N N

S

NH

Methyl chloroformate

Hydrazine hydrate

O

NHNH2

RCHO

F

ClCl

N N

S

NH

O

NHN R

HSCHCOOHX

F

ClCl

N N

S

NH

O

NH NS

O

R

X

(51)

(53)

(54)

(52)

R=aryl; X=H, CH3, CH2COOH

Terioglu et al. synthesized series of 5-nitro-3-[(5-nonsubstituted/methyl-4-thiazolidinone-2-ylidene) hydrazono]-lH-2-indolinones (56) by cyclization of 5-nitro-lH-indole-2,3-dione-3-thiosemicarbazone (55) with ethyl bromoacetate or ethyl 2-bromopropoinate [20].

NH

O

N NH CS

NH2

NH

O

N NS

HN O

RO2N

O2N

(55) (56)

Cacic et al. reported the cyclizaiton of thiosemicarbazide (57) with chloroacetylchloride in chloroform which afforded thiazolidinone derivative (58) [21].

O OHO

O

NH NH NH

S

O OHO

ONH N N

SO

(57) (58)

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 286

Mir et al. reported a rapid and easy solvent free one-pot synthesis of 5-arylidne-2-imino-4-thiazolidinones (61) by condensation of the thioureas (59) with chloroacetic acid and an aldehyde (60) under microwave-irradiation [22].

R1HN NHPh

S+ R2CHO ClCH2COOH S

NR1

NPhR2

(59) (60) (61)

R1=Ph, 4-Methylpyridin-2-yl

OMe NMe Me

NMe Me

O

OR2

=

Cao et al. reported the reaction of 1,4,5,6-tetrahydro-6-pyridazinone-3-carboxylic acid hydrazides (62) with aromatic aldehydes which afforded 1,4,5,6-tetrahydro-6-pyridazinone-3-cabonyle aromatic aldehyde hydrazones (63). Hydrazones (63) cyclized with mercaptoacetic acid in DMF in the presence of anhydrous ZnCl2 to afford 1,3-thiazolidinone derivative (64) [23].

HN NO C

ONHNH2

RCHO

HN NO C

ONHN CH R

(62) (63)

HN NO C

ONHN CH R

SO

HSCH2COOH

(64)

R=C6H5, p-MeOC6H5, p-NMe2C6H5, o-NO2C6H4, m-NO2C6H4, m-Ome-p-OHC6H3

Rollas and Kucukguzel synthesized 4-thiazolidinones (66) by reacting hydrazones (65) reacted with mercaptoacetic acid/thiolactic acid [24].

Ar CO

NH N CH R Ar CO

NH N CH RSO

R

(65) (66)

Turgut et al. prepared 4-thiazolidinones (69) by the Katti cabodiimide (DCC) mediated one-pot three component condensation reaction of an aromatic amine (68), an aldehyde (67) and mercaptoacetic acid [25].

H

OCH3O

CH3O

CH3O

+ NH2XCH3O

CH3O

CH3ONS

O

X

(67) (68) (69)

X=CH3, Cl, OC6H5, OCH3, OC2H5

Shiradkar reported that various aryl-thioureas (70) on treatment with ethyl chloraoacetate (71) and fused sodium acetate in a ethanol gave 2-arylimino-4-thiazolidinones (72) [26].

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 287

Ar NHCS

NH2 + ClO

C2H5O

CH3COONa NHS O

NAr

(70) (71) (72)

Ameta et al. reported a fast and facile procedure for the synthesis of pyridothiazolidinone (76) starting from dihydropyridine (73). Oxidation of (73) with nitrating mixture (HNO3/H2SO4) produced the anticipated 2,6-dimethylpyridine derivatives (74), which were subsequently condensed thiosemicarbazide in ethanol to produce the key intermediate 2,2-[4-(4-substitutedphynely)-2,6dimethylpyridine-3,5diyl] dicarbonyldihydrazine carbothiomides (75). Compound (75) finally provided (76) on reacting with ClCH2COOH and CH3COONa. All the reaction were carried by conventional as well as microwave method. The potent antimicrobial effects of the synthesized compounds were also investigated [27].

NH

Ar

OCH3

OH3C

CH3H3C

OO

N

Ar

OCH3

OH3C

CH3H3C

OO

HNO3 , H2SO4

(73) (74)

Thiosemicarbazide

8-10 minN

Ar

NHNH

HN

CH3H3C

OO

NHCS

NH2C

H2N

S

(75)

ClCH2COOHCH3COONa 6-8.3 min

N

Ar

NHNH

N

CH3H3C

OO

N

NH

S

O

S

NHO

(76)

Ar=4-F-C6H4, 4-Cl-C6H4, 4-OCH3C6H4, 4-NO2-C6H4, C6H5

Yan et al. reported the construction of 4-thiazolidnone ring (79) by a three component reaction of fluorous benzaldehydes (78), an amine and mercaptoacetic acid. Compound (78) was readily prepared form (77) [28].

CHO

R1

HO C8F17SO2F

K2CO3/DMFCHO

R1

OSO

OC8F17

R1

OSO

OC8F17

S

NHO

R3

(77) (78) (79)

Talesara et al. also synthesized 2-amino-5-(4'-pyridyl)-1,3,4-thiadiazole (81) by cyclization of iso nicotinoyl thiosemicarbazide (80) with conc. sulphuric acid. When (81) was refluxed with various aldehydes. It gave the corresponding arylidene derivatives (82) which on further treatment with mercaptosuccinic acid furnished thiazolidinone derivative (83). Another thiazolidinone derivative 2-isonicotinoylhydrazido-1,3-thiazolidinone (84) was obtained by the successive treatment of isonicotinoylthiosemicarbazide (80) with chloroacetic acid in the presence of sodium acetate [29].

[Ar=4-OCH3C6H4, 3,4,5-OCH3C6H2, 3-NO2C6H4, 4-NO2C6H4, 4-(CH3)2NHC6H4, C6H5, C4H3O(2-furyl)].

O

NHNH

NH2

SS

NNNH2

S

NNN

R (80) (81) (82)

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 288

S

NNN

Mercaptosuccinicacid

Ar

SO

O

OH

ClCH2COOH

O

NH

N

S

HN

O

(84) (83)

Literature has revealed that very few steroidal thiazolidinones have been prepared and studied so far. Shafiullah and Ali reported the synthesis and mass spectral studies of the spiro thiazolidinones (85) and (86). Steroidal thiazolidinones of cholestane series (87) and (88) were also prepared by cyclizing the respective thiosemicarbazones with ClCH2COOH [30].

C8H17

H

H

H

HN S

O

C8H17

H

H

H

HN S

O (85) (86)

C8H17

H

H

HNN

HN

SO

C8H17

H

H

H

N NHN

SO

AcO

(87) (88)

Siddiqui et al. prepared C-24 thiazolidinone derivatives (90) [R=H, OH, R1=H] of bile acids from esters (89) [R2=OMe] in three steps involving hydrazinolysis with NH2NH2 to give (89) [R2=NHNH2], reaction with potassium or ammonium thiocynate to give (89) [R2=NHNHC(S)NH2] and finally cyclocondensation with chloroacetic acid in presence of anhydrous sodium acetate and AcOH [31].

H

H

H

COR

H

H

H

CHONH

R1N

S

O

(89) (90)

Shamsuzzaman and Siddiqui reported the synthesis of 3-Diazo(4ʹ-thiazolidinone) cholest-4-ene (93) from cholest-4-en-3-one thiosemicarbazone (92) and chloroacetic acid in presence of sodium acetate. The compound (92) was obtained by reacting cholest-4-en-3-one (91) with thiosemicarbazide in presence of conc. HCl [32].

C8H17

OH

H

H

C8H17

N

NHS

NH2

H

H

HThiosemicarbazide

C8H17

NN

H

H

H

HN

SO

ClCH2COOH / AcONa

(91) (92) (93)

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 289

Shih et al. reported the synthesis of 5-(3-Arylsydnon-4-ylmethylene)thiazolidine-2,4-diones (95 a-d) and 5-(3-Arylsydnon-4-ylmethylene)-2-thioxothiazolidin-4-ones (96 a-d) from 3-aryl-4-formylsydnones (94 a-d) in high yields by the modified Knoevenagel condensation [33].

NO

N

CHOAr

O

AcONa

CH3COOH

S

NH

O

O

S

NH

O

S

NO

N

Ar

O

S NH

O

O

SNH

O

S

NO

N

Ar

O

(94)

(95)

(96)

Ar=C6H5; b: Ar=p-CH3C6H4; c: Ar=p-CH3OC6H4; d: Ar=p-C2H5OC

All the synthesized thiazolidine derivatives (95a-d, 96a-d) were screened by paper-disc method to identify their antimicrobial activities against three bacteria viz. Staphylococcus aureus, Proteus vulgaris and Escherichia coli, and two fungal cultures viz. Aspergillus niger and Penicillium citrinum. The reference drugs were Norfloxacin and Griseofulvin, respectively. The screening data indicated that the tested sydnonyl-substituted thiazolidine derivatives exhibited no obvious antibacterial activity compared with the standard drug Norfloxacin. However, thiazolidine derivatives displayed significant antifungal activities against Penicillium citrinum and Aspergillus niger.

Zhou et al. reported the synthesis of library of 2-Arylimino-5-arylidene-thiazolidin-4-ones (101) by reacting 2-Arylimino-thiazolidin-4-ones (100) with different benzaldehydes. The compound (100) was obtained after reacting chloroethyl acetate with primary thiourea (99) in presence of sodium acetate. The compound (99) was obtained by the reaction of primary anilines (97) and NH4SCN in 10 mL of 6 N HCl or from the rection of corresponding thiourea (98) with NH3 H2O. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM [34].

Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 290

Conclusion In this article we have mentioned the different routes for the synthesis of thiazolidinone derivatives. The steps included condensation followed

by cyclization or multi component reaction (MCR), either in a step-wise manner or in one pot has been achieved successfully to obtain the aforementioned class of heterocycles under different conditions. Most of the preparative methods included mercaptoacetic acid, thiolactic acid, chloroacetyl chloride, potassium thiocyanate, ethylchloro acetate and ammonium thiocyanate are the most common reagents for the synthesis of thiazolidinone appended on different heterocyclic skeletons. Also many series of substituted thiazolidinone -fused five membered heterocycles possessing N-, S- and O- have been constructed in potential yields and with conventional methods. Hence these protocols provide convenient strategies to annelate different heterocyclic nuclei with widespread bioactive thiazolidinone thereby extending the categories of heterocyclic systems. These strategies may also provide valuable information for the further design and development of more active biological agents through various modifications and derivatizations.

Acknowledgements

Authors (AMD and AM) thank Dr. Shamsuzzaman, Professor of Chemistry, AMU Aligarh, for useful discussions during the literature survey and University Grants Commission for providing research fellowship for successful completion of this work. Author (AM) is thankful to the Chairperson, Department of Pharmacy, UST, Sana’a, Yemen.

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Citation: Mashrai A, Dar AM, Mir S, Shamsuzzaman (2016) Strategies for the Synthesis of Thiazolidinone Heterocycles. Med chem (Los Angeles) 6: 280-291. doi:10.4172/2161-0444.1000358

Med chem (Los Angeles)ISSN: 2161-0444 Med chem (Los Angeles), an open access journal

Volume 6(4): 280-291 (2016) - 291

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