INTRODUCTION:

Sir Alexander Fleming accidentally discovered an antibacterial property of penicillin in 1929 and this was largely credited with initiating the modern antibiotic era. Then he explained that antibiotics are the substances produced by microorganisms, which suppress the growth or kill other microorganisms at very low concentration. He predicted that internal fluids, organs and body structure are sterile under normal circumstances and the presence of bacteria, fungi, viruses etc., in their places was diagnostic evidence of infection.

A large number of medicinal compounds which have been discovered belong to a major class of heterocycles containing nitrogen and/or sulphur. The versatile synthetic applicability and biological activity of these heterocycles has helped the medicinal chemist to plan, organize and implement new approaches towards discovery of novel drugs.

Nitrogen and/or sulphur containing heterocycles constitute an important class of compounds in medicinal chemistry. There has been considerable interest in the development of synthetic methods for the production of pyrimidines, indoles, thiazolidine and oxazolidine derivatives. This seems to be because they represent very active classes of compounds, possessing a wide spectrum of biological activities.

These classes of compounds are known as ‘Thiazolidines’, which contain both ‘thia’ (sulphur) and ‘aza’ (nitrogen) atoms in a cyclic 5 membered ring. Along with these two heteroatoms, a ‘ketone’ group was introduced to form a novel ring system called ‘Thiazolidinone’, which has given a big blow to the bacterial and fungal resistance by many of the drugs and antibiotics. But ketone groups can be attached throughout the ring system at different positions like 2, 4 and 5.

2-Thiazolidinone

4-Thiazolidinone

5-Thiazolidinone

In the recent past years, attention has been focused on synthesis of substituted heterocycles and their analogs, due to their increasing medicinal importance. The presence of linkage N-C-S in thiazolidinone is believed to account for antifungal activity and better chemotherapeutic agent against awful threats.

The historical importance of thiazolidinones was emphasized during the period 1941-45, when work on the structure of penicillins showed the presence of thiazolidine ring in it. Compounds carrying the thiazolidinone ring have been reported to demonstrate wide range of pharmacological activities, like antibacterial, antifungal, antitubercular, anticonvulsant, analgesic, antihistaminic, anaesthetic, antithyroid, antiparkinsonism, anti-inflammatory, anticancer, antimalarial, anthelminitic, pesticidal etc.

BIOLOGICAL SCREENING OF 4-THIAZOLIDINONES

Review of literature reveals that the thiazolidinones and its derivatives possess various activities and can be synthesized by various methods as discuss below:

1. Priya et al., reported the synthesis of a series of thiazolidinone derivatives of 1,2-benzisoxazole-4-hydroxy-2H-chromen-2-one is condensed with aromatic aldehyde to yield Schiff’s base, which on cyclization with mercaptoacetic acid yields thiazolidinone derivatives of benzisoxazole. The synthesized compounds were screened for In vitro antibacterial and antifungal activity by turbidimetric methods.^[1]

2. Archana synthesize various 2-N-(2-phenyl-1H-indol-3yl)-imino benzene/thiophenol, 3-Chloro-1-(benzyl/ thiophenyl)-4-(2-1H-indol-3yl) azetidin-2-ones and 3-substituted benzyl/thiophenyl -4-(2-phenyl 1H-indol-3-yl) thiazolidin-4-ones and were screened in vivo for their acute toxicity and anticonvulsant activity in MES and PTZ models.^[2]

4. Gaikwad SV et al., reported the synthesis of 2-acetyl-substituted-1-naphthol by the acetylation of substituted-1-napthol in presence of glacial acetic acid and zinc chloride. This compound on treatment with KCNS and Br₂ yielded 2-(2-amino-1,3-thiazol-4-yl)-substituted-naphthalen-1-ol, which on facile condensation with aromatic aldehyde gave Schiff Bases. These on cyclo-condensation reaction with mercaptoacetic acid yields 4-thiazolidinone derivatives. Newly synthesized compound were also studied for their antimicrobial activities.^[3]

5. Belwal CK et al., synthesize a series of novel Schiff bases containing N-benzyl piperidine moiety by the reaction of N-benzylpiperidine-4-carbaldehyde with suitable aromatic amines and synthesized Schiff bases were converted to a series of novel 4-thiazolidinones by the reaction of Schiff base with mercaptoacetic acid. All the compounds were screened for their antimicrobial activity against some selected pathogenic microorganism. Good level of antimicrobial activity has been displayed by both categories of compounds against tested pathogenic microorganism. Thiazolidinone derivatives showed higher activity than Schiff base derivatives.^[4]

6. Reddy CS et al., synthesize a series of 2-(3,5-dimethyl-1-phenyl-1H-4-pyrazolyl)-3-(aryl/heteroaryl)-1,3-thiazolidin-4-one derivatives in one pot from 3,5-dimethyl-1-phenyl-1H-4-pyrazolecarbaldehyde. These compounds were screened for antibacterial activity against Bacillus subtilis, Staphylococcus aureus, E. coli and Staphylococcus pyrogenes.^[5]

7. Patil TS et al., reported the synthesis of some novel 2-(4-substituted phenyl)-3-(4-substituted phenyl)-5-methylthiazolidine-4-ones by condensing 4-substituted anilines with 4-substituted benzaldehydes by using ethanol as solvent. The synthesized compounds were heated with 2-mercaptopropionic acid in excess of benzene. The compounds were screened for antibacterial and antifungal activity.^[6]

8. Mogilaiah K et al., reported the synthesis of 2-aryl-3-(1,8-naphthyridin-2-one-3-carbonylamino)-4-thiazolidinones from cyclocondensation of 1,8-naphthyridin-2-one-3-carboxylic acid arylidene hydrazide with mercaptoacetic acid in DMF in the presence of anhydrous zinc chloride. These compounds were screened for antibacterial activity against Gram positive and Gram negative bacteria.^[7]

9. Didwagh SS et al., reported the synthesis and antimicrobial evaluation of novel 3-(4,6-diphenyl-6H-1,3-thiazin-2-yl)-2-(4-methoxyphenyl) thiazolidin-4-one derivatives by the condensation-cyclization reaction of 4,6-diphenyl-6H-1,3-thiazin-2-amine, aromatic aldehyde and thioglycolic acid in polypropylene glycol at 110⁰C temperature.^[8]

10. Gupta V et al., synthesized the 4-acetamidophenoxyacetylhydrazide from paracetamol on reaction with different aldehyde give Schiff base, which on treated with mercaptoacetic acid to produce various thiazolidinone derivatives. Antimicrobial activity of compounds were evaluated by cup-plate method.^[9]

11. Purohit SS et al., reported the synthesis and antimicrobial activity of a new series of 3,5-disubstituted thiazolidine-2,4-diones likes 3-aryl-5-arylidine thiazolidin-2,4-dione derivatives.^[10]

12. Sharma R et al., reported the synthesis of phthalimido (2-aryl-3-isonicotinamido-4-oxo-1,3-thiazolidine-5-yl) ethanoates. All the synthesized compounds were screened for antibacterial and antifungal activities.^[11]

R= Phthalimidoxy

13. Shetgiri NP et al., reported the synthesis of 4-(substituted-1-phenyl methyl hydrazine)-N-substituted phenyl succinimides from maleic anhydride and evaluate their antimicrobial activity against Gram positive, Gram negative and fungal organisms.^[12]

14. Lather V et al., reported the synthesis and antimicrobial activity of N¹-(arylidine hydrazidomethyl)-indoles, 2-(substituted aryl)-3-(N¹-indolyl acetamidyl)-4-oxo-thiazolidine and 5-benzylidene derivatives of thiazolidinones. Here efforts were made to combine the separate groups of similar activity into one compound leading to changes in biological activities. The compounds were tested in-vitro against Staphylococcus aureus, Bacillus subtilis, E. coli, Salmonella typhi, Pseudomonas aeruginosa, Proteus vulgaris, Candida albicans and Aspergillus niger.^[13]

15. Datta NJ et al., reported the synthesis of thiazolidinones by condensation of thioglycollic acid /thiolactic acid with N-aryl-2-chloroquinoline-3-yl-azomethine. All the compounds have been screened for antimicrobial activity.^[14]

16. Deasi NC et al., synthesize the several methyl 2-{2-[4-oxo-3-(arylcarbonylamino)-1,3-thiazolidin-2-yl] phenoxy}acetates, methyl 2-{2-[3-chloro-4-oxo-1-(arylcarbonylamino)azetidin-2-yl] phenoxy}acetates and were evaluate for their in-vitro activity against several microbes.^[15]

17. Mogilaiah K et al., reported the synthesis and antibacterial activity of 4-thiazolidinone and 2-azetidinone derivatives like 2-aryl-3-(2-trifluromethyl-1,8-naphthyridine-3-carbonylamino)-4-thiazolidinones from 2- trifluoromethyl-1,8-naphthyridine.^[16]

18. Mogilaiah K et al., reported the synthesis of 1,8-naphthyridinyl-4-thiazolidinones and evaluate for their antifungal and antibacterial activities.^[17]

Ar=Aryl Aldehydes

19. Shah M et al., reported the synthesis of various 2-aryl-3-N-(6-phenylthieno [3,2-d] pyramid-4-yl-amino)-5-H/methyl-4-thiazolidinones and 4-aryl-3-chloro-1-N-(6-phenylthieno [3,2-d] pyramid-4-yl-amino)-2-azetidinones. All the compounds evaluate for their in-vitro activity against several Gram positive, Gram negative and fungal organism.^[18]

20. Kidwai M et al., reported the reaction of 3,5-dinitrobenzoic acid with thienyl chloride yields 3,5-dinitrobenzoate, which on condensation with different aldehydes produce 2-(3,5-dinitrobenzoyl) hydrazones, which on condensation with thioglycollic acid and chloroacetyl chloride produce 2-aryl-3-[(3,5-dinitrobenzamido)]-thiazolidinones and N-[3,5-dinitrobenzamido]-3-chloro-4-(aryl substituted)-azetidinones and were examined for antibacterial and antifungal activity.^[19]

21. Patel RB et al., reported the synthesis of 2-aryl-3-[4-(4-chlorophenyl)-6-(3,4,5-trimethoxyphenyl)pyrimidin-2-yl-ureido]-4-thiazolidinones derivatives and evaluate for antifungal, antibacterial and antitubercular activities against different microorganism.^[20]

22. Hirpara SB et al., reported the synthesis of 2-(arylidenehydrazono)-3-(2-methoxy-5-methylphenyl)-4-thiazolidinones by the condensation of 2-methoxy-5-methylphenyl thiosemicarbazide with various aldehydes. The compounds are evaluated for several microbes and screened for antitubercular activity against Mycobacterium tuberculosis H₃₇R_v, Some compounds evaluated for in-vitro anticancer screen.^[21]

23. Oza H et al., synthesized the various 4-thiazolidinones by the cyclocondensation of various Schiff base with thioglycolic acid and thiolactic acid. All the derivatives were screened for anti-tubercular activity against Mycobacterium tuberculosis H₃₇R_v.^[22]

24. Bhaumik A et al., synthesize the N-[2-(4-substituted phenyl)-4-oxo-1,3-thiazolidine-3-yl]-2-(naphthalene-2-yloxy)acetamide and evaluate for anticonvulsant activity. Some derivatives have shown protection against MES induced seizure.^[23]

25. Archana et al., synthesized a series of 2-(substituted aryildenyl imino)-5-(3-indolomethylene)-1,3,4-thiadiazole via condensation of 2-amino-5-(3-indolomethylene)-1,3,4-thiadizole with various aromatic aldehyde. When thioglycolic acid is added they produce various derivatives of 3-[5-(3^’’-indolo-methylene)-1^’,3^’,4^’-thiadiazole-2-yl]-2-substitutedaryl-4-thiazolidinones. These heterocyclic substituted indoles showed high level of protection against Maximal Electro Shock (MES) induced convulsion in animal models. These compounds were screened for anticonvulsant activity and acute toxicity.^[24]

R=H, N (CH₃)₂, 4-CH₃

26. Srivastava SK et al., condensed the various aldehyde with N¹⁰-(acetohydrazido)-2-chlorophenothiazine yield arylidenacetohydrazido-2-chlorophenothiazine, which on cycloaddition of mercaptoacetic acid then reacted with various aldehydes produce 5-arylidene-2-aryl-3-(2-chlorophenothiazinoacetamidyl)-1,3-thiazolidin-4-ones. The compounds were screened for antifungal and anticonvulsant activities.^[25]

27. Yadav R et al., reported the synthesis of several 2-[(aryl)-3-(acetylamino)1,3-thiazolidinones]-2-mercaptobenzothiazole from 2-mercaptobenzothiazole and were tested for antimicrobial and anti-inflammatory activities.^[26]

28. Mohd A et al., reported the synthesis and biological screening like antibacterial and anti-inflammatory activities of various 2,5-disubstituted-1,2,4-triazole, 1,3,4-thiadiazole/oxadiazole and 2,3-substituted-4-thiazolidinone derivatives.^[27]

29. Lodhi RS et al., reported the synthesis of 2-(substituted aryl)-3-(N¹imidazolyl-acetamidyl)-4-oxo-thiazolidines and 2-(substituted aryl)-3-(N¹imidazolyl-acetamidyl)-5-arylidene-4-oxothiazolidines and tested for anti-inflammatory, antifungal and antibacterial activities.^[28]

30. Srivastava SK et al., reported the synthesis and biological screening of 5-arylidene-2-aryl-3-[(2-benzothiazolylthio)-acetamidyl)]-1,3-thiazolidin-4-ones. The incorporation of 4-oxo-thiazolidines and 5-arylidine moieties in 2-mercaptobenzothiazole framework has been found to enhance the various activities such as hypnotic, anaesthetic, antifungal, antiviral and anthelmintic. In this study, 2^nd position in 2-mercapto benzothiazole having thiol (SH) group was used as the target for chemical change. The synthesized compounds were screened for antifungal, antibacterial and anti-inflammatory activities. The anti-inflammatory activity determine against the carrageenan induced rat paw oedema in albino rats and anthelminitic activity against the experimental infection of Ancyclostoma Ceylanicum and Hymenolepsis nana in rats. Some of compounds show exhibit appreciable activity.^[29]

R₁= H, CH₃

R₂= Substituted aldehydes

R₃= H, CH₃

R₄= Substituted aldehydes

31. Asati KC et al., reported the synthesis of 5-arylidene-2-aryl-3-(benzotriazoloacetamidyl)-1,3-thiazolidine-4-ones from benzotriazole and various aromatic aldehydes. The synthesized compounds were tested for analgesic activity in albino rats by Eddy and Leimbach method. They were also screened for antifungal and antibacterial activities by paper disc techniques.^[30]

A_r= -ClC₆H₄/ -CH₃C₆H₄/ -NO₂C₆H₄/ -BrC₆H₄

32. Srivastava SK et al., reported the synthesis of 5-arylidene-2-aryl-3- (1,2,4-triazoloacetamidyl)-1,3-thiadiazol-4-ones from 1,2,4-triazoles as starting material. All the compounds were screened for their antibacterial, antifungal, analgesic and diuretic activities. Diuretic activity was tested by Lipschiz method in adult male rats, fasted overnight with free access to water loaded orally by normal saline.^[31]

A_r= Substituted aldehydes

33. Vagdevi HM et al., synthesize the 2-[2-(-aryl-4-thiazolidinone)thiazol-4-yl]naphtha[2,1-b]furans from Schiff base 2-(2-arylideneaminothiazol-4-yl)naphtha[2,1-b]furans on reacting with various aldehyde. Which have been screened for antimicrobial and anthelmintic activities. Selected compounds have been evaluate for anti-inflammatory activity by winter’s hind paw method and diuretic activity on albino rats.^[32]

34. Singh T et al., prepared several pyridinylthiazolylazetidinones, pyridinylthiazolythiazolidinones and pyridinylthiazolylformazones from pyridinylthiazolylarylidines. These compounds screened for antifungal, antibacterial and insecticidal activities. The insecticidal activity was determined on cockroaches (Periplaneta americana) of either sex.^[33]

R= Substituted aldehydes

35. Mohd I et al., reported the synthesis of 2-(substituted phenyl)-3-[{4-(1-naphthyl)-1,3-thiazol-2-yl} amino]-5-methyl-1,3-thiazolidin-4-ones by cyclization of 4-(1-naphthyl)-2-(substitutedbenzylideneamino)-1,3-thiazoles with thiolactic acid in dioxane using zinc chloride. The synthesized compounds were screened for antihyperglycemic activity in two phases. Phase-I involved evaluation of blood lowering ability in normal rats in sucrose loaded model while in phase-II study included the evaluation of blood sugar by alloxan model. All the compounds show good antihyperglycemic activity.^[34]

36. Lee HW et al., reported the molecular design and synthesis of novel pyrimidine derivatives having thiazolidinone. The synthesized compounds were evaluated for their glucose and lipid lowering activity in KKA^Y Mice and their hypoglycemic and hypolipidemic activities studied.^[35]

CONCLUSION:

In this review we explain the various routes for the synthesis of thiazolidinone derivatives. The steps included condensation followed by cylization either in one pot or step-wise manner to obtain the aforesaid class of heterocycles under different conditions. Most of the synthetic procedure included chloroacetyl chloride, mercaptoacetic acid, ethylchloroacetate and potassium thiocynate are the most common reagents for the synthesis of thiazolidinone with various heterocyclic compounds. This review also report the different biological activities like, antimicrobial, anticonvulsant, antitubercular, anti-inflammatory, analgesic, diuretic and antihyperglycemic of thiazolidinone. A variety of drugs in market today posses thiazolidinone ring and ongoing research is focused on developing newer antibiotics in which thiazolidinone play major role. Hence it can be concluded that this review provide the strategies for the design and development of potent biological agents through various modifications.

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Received on 26.03.2017 Modified on 30.03.2017

Asian J. Research Chem. 2017; 10(2):240-248.

DOI: 10.5958/0974-4150.2017.00039.6