INTRODUCTION:
Heterocyclic compounds represent one of the most active classes of compounds possessing a wide spectrum of biological activities, including antibacterial, antifungal and other biological activities. Further, the treatment of infectious diseases still remains an important and challenging problem because of a combination of factors including emerging infectious diseases and the increasing number of multi-drug resistant microbial pathogens. In spite of a large number of antibiotics and chemotherapeutics available for medical use, at the same time the emergence of old and new antibiotic resistance created in the last decades revealed a substantial medical need for new classes of antimicrobial agents. There is a real perceived need for the discovery of new compounds endowed with antimicrobial activity1. There are various problems arising with the use of antimicrobials such as local tissue irritation, interference with wound healing process, hypersensitivity reactions, systemic toxicity, narrow antimicrobial spectrum, development of resistance.
So the increasing clinical importance of drug-resistant microbial pathogens has made additional urgency in microbiological research2. A wide variety of heterocyclic systems have been explored for developing pharmaceutically potent molecules. Among them, the derivatives of Thiazolidinones have been playing an active role in medicinal chemistry.
Thiazolidinone is (I) the derivative of thiazolidine (II) with a carbonyl group at position 4. There may be substitution at 2, 3 and 5 position but group attached to the carbon atom in the 2-position of III brings about difference in structure and properties.
I II III
There has been a considerable interest in the chemistry of thiazolidin-4-one ring system, which is a core structure in various synthetic pharmaceuticals displaying a broad spectrum of biological activities. Thiazolidinone ring also occurs in nature; thus actithiazic acid isolated from Streptomyces strains exhibits highly specific in vitro activity against Mycobacterium tuberculosis3. Thiazolidinone derivatives are also known to exhibit diverse bioactivities such as anti-convulsant4, antidiarrheal5, anti-platelet activating factor6, antihistaminic7, anti-diabetic8, cyclooxygenase (COX) inhibitory9, Ca2+channel blocker10, platelet activating factor (PAF) antagonist11, cardioprotective12, anti-ischemic13, anti-cancer14, tumor necrosis factor-α antagonist15, nematicidal16, anti-HIV17, non-peptide thrombin receptor antagonist18, antifungal activity19, antitubercular20, anti-inflammatory21, antiproliferative22, analgesic23, anti-Toxoplasma gondii24, antiparkinsonism activity25, antioxidant activity26 and hypoglycemic27 activities. However, literature survey revealed that linked heterocycles containing thiazole and thiazolidinone have seldom been reported. The present review attempts to summarize the various derivatives of thiazolidinone alongs with their antimicrobial potential.
Antimicrobial potential of thiazolidione derivatives
Ranjana et al28 synthesized phthalimido[2-aryl-3-(5'-(4''-pyridyl)-1',3',4'-thiadiazol-2'-yl)-4-oxothiazolidin-5-yl]ethanoates and evaluated their anti-microbial activity using different bacterial strains such as Escherichia coli, Proteus vulgaris, Klebsiella pneumoniae, Pseudomonas auregenosa, Salmonella typhi and Bacillus subtilis by cup plate method. In their studies they found that the synthesized compounds have shown very little activity against B.subtilus, P. vulgaris and S. typhi, moderate activity against E. coli and very strong activity against K. pneumoniae and P. auregenosa as compared to standards used i.e. Ciprofloxacin and Gentamicin. They found that compounds containing electron withdrawing group exhibited better activity and donating group causes less activity.
Ameya et al29 synthesized 2-[5-(arylidene)-2-imino-4-oxo-thiazolidin-3-yl]benzothiazole-6-carboxylic acid and evaluated their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Psuedomonas aeruginosa and Escherichia coli by Cup plate method and antifungal activity against four different fungi such as C. albicans, C. pannical, A. niger and R. oryzae by filter paper disc technique. In their studies they found that all the newly synthesized compounds showed antibacterial activity against S. aureus, B. subtilis, P. aeruginosa and E. coli and show slight to moderate antifungal activity.
Vagdevi H.M et al30 synthesized 2-[2-(2-Aryl-4-thiazolidinono)thiazol-4-yl]naphthafurans and found their antimicrobial activity against S. aureus, K. pneumonia, A. niger and C. albicans by cup-plate method.
Patel et al31 synthesized 3-(4-(naphthalen-2-yl)thiazol-2-yl)-2-arylthiazolidin-4-one derivatives and evaluated antibacterial activity against B. subtillis, S. aureus, E. coli, S. typhi found that compounds containing 4-methoxy phenyl, 2-hydroxy phenyl and 4-methyl phenyl were more active against the tested microbes.
Tejaskumar et al32 synthesized a series of 2-(substitutedphenyl)-3-[4-(2,4-dichloro-5-fluorophenyl)-6-(2thienyl)pyrimidine-2ylureido]5H/methyl/carboxymethyl-4-thiazolidinones and evaluated their antibacterial activity against E. coli, P. aureginosa, S. aureus and B. substilis using the cup-plate agar diffusion method and antifungal activity against C. crusei and C. albicans. In their study they found that some of the compounds possess considerable antibacterial activity due to the presence of methoxy, fluoro and chloro groups. However the activity of the tested compounds is less than that of streptomycin and some of the compounds possess good anti fungal activity. However, none of compounds was superior to standard used against any of the fungi.
Bhoot et al33 synthesized 2-arylimino-3-aryl-5-[5′-(3,4-dichlorophenyl)-2′furylidene]-4-thiazolidinones and evaluated their anti microbial activity against B. megaterium, S. aureus, E. coli, P. vulgaris, A. niger and in their study they concluded that remarkable inhibition was observed in compounds bearing R = phenyl, 2-methoxyphenyl, 2-methylphenyl, 3-methylphenyl 4-nitrophenyl substituents.
Sharma et al34 synthesized N-(5-methyl-4-oxo-thiazolidin-3-yl)-nicotinamide and investigated antimicrobial activity against B. Subtilis, S. aureus, E. coli, A. niger and C. albicans. In their study they found that the positive coefficient of the log P descriptor, which relates to the hydrophobicity of the molecule, suggested that an increase in the lipophilicity might increase the activity. This corresponds to the presence of hydrophobic binding site in the N-(5-Dimethyl-4-oxothiazolidin-3-yl)-nicotinamide.
Ravi Kumar et al35 synthesized 2-(substituted phenyl)-3-substituted phenoxyacetamido-4-thiazolidinones and investigated anti-bacterial activity of against S. aureus, B. subtilis, E. coli and P. aeruginosa and antifungal activity against C. albicans and A. niger. They used Ampicillin and Griesofulvin (6μg/cup and 25μg/cup respectively) as standard reference drugs. In their study they found that compounds having electron releasing groups like methyl, hydroxy and methoxy may be responsible for antibacterial and antifungal activities.
Hui-Ling et al36 synthesized 2-Imino-3-(4-arylthiazol-2-yl)-thiazolidin-4-ones and their 5- arylidene derivatives and evaluated their fungicidal activity against 7 agricultural fungi, Pleurotus ostreatus, Aspergillus niger, Pythium aphanidermatum, Gaeumannomyces graminis, Fusarium graminearium, Pyricularia oryzae and Botrytis cinerea, by the agar growth medium poison technique. In their study they found that compounds (where Ar is 2,4-(Cl)2-5-FC6H2 and 2,4-(Cl)2C6H3 have higher fungicidal activity than the others. Compounds (where Ar is C6H5, p-ClC6H4, 2,4-(Cl)2-5-FC6H2 and 2,4-(Cl)2C6H3 were more fungicidal against Pythium aphanidermatum than against the other 6 fungi. Introduction of benzylidene group at C-5 decreased the fungicidal activity. The inhibition of all of the 5-arylidene-4-thazolidinones was low.
Feray et al37 synthesized 5-Benzylidene-3-(4-substitutedphenyl)-2-(2-pyrrolyl)-4- thiazolidinone and evaluated their anti tubercular activity against Mycobacterium tuberculosis. In their study they found that compounds (where x = ethoxy and chloro) gave zone diameter of growth inhibition less than 20 mm.
Desai et al38 have synthesized five membered sulfur containing heterocyclic derivatives 2-(aryl)-3-[2-(benzothiazolylthio)-acetamidyl]-4-oxo-thiazolidines. All the compounds have been screened for their antibacterial activity against E. coli, S. aureus and B. substilis.
A series of 2-(substituted phenyl)-3-[4-(2,4-dichloro-5-fluorophenyl)-6-(2-thienyl)pyrimidine-2-yl-ureido]-5H/methyl/carboxymethyl-4-thiazolidinones were prepared. All the derivatives were screened for antibacterial activity39.
Kavitha et al40 carried out the synthesis of some novel bioactive venlafaxine analogs such as 2,3-disubstituted-1,3-thiazolidin-4-ones. All the synthesized compounds were screened for their efficacy as antimicrobials in vitro by the disk diffusion and micro dilution method against pathogenic strains such as B. subtilis, E. coli, P. fluorescens, X. campestris, X. oryzae, A. niger, A. flavus, F. oxysporum, T. species and F. monaliforme species. From the results obtained, it revealed that the presence of two fluorine atoms at 2nd and 6th positions might be the reason for the significant inhibitory activity.
Some new and biologically active [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-2-aryl-thiazolidinone-4-ones were synthesized by reaction of Schiff bases with mercapto acetic acid in presence of THF with adding anhydrous ZnCl2. The compounds were evaluated for their antibacterial activity against B. subtilis, S. aureus, P. aeruginosa and E. coli. Some of the tested compounds showed significant activity41.
The preparation of various 6-methyl-2-oxo-N-(4-oxo-2-phenylthiazolidin-3-yl)-4-phenyl-1,2-dihydro pyrimidine-5-carboxamide was carried out by Haitham et al42. The synthesized compounds were screened for their in-vitro antimicrobial activity. The investigation of antimicrobial screening data revealed that most of the compounds tested have demonstrated congruent activity.
2-[(2'-chloro-7'-methoxyquinoline-3'-yl)]-3-[3''-hydroxy-6''-(substitutedphenyldiazenyl)phenyl]-5-methyl-1,3-thiazolidin-4-one derivatives were prepared by Rana et al43. The reaction was carried out by both conventional and microwave methods. The compounds have been screened for their antibacterial and antifungal activities against different microorganisms. The compounds were tested by Disk Diffusion Method on Muller Hinton Agar at concentration of 128, 256 and 512 μg/mL. The presence of fluoro, bromo or chloro group in the moiety enhances its biological activity.
Some new Schiff bases containing thiadiazole, sulphonyl hydrazide and 4-thiazolidinone moieties, were synthesized and evaluated for their antimicrobial activity with a view to obtain better pharmacologically active compounds. Antibacterial and antifungal activities of synthesized compounds were done in comparison with Streptomycin and Griseofulvin as the standard drug by agar well diffusion method. All the selected strains of the bacteria and fungi namely S. aureus, E. coli, K. pneumonea, A. niger and A. flavus showed sensitivity to most of the derivatives at concentration of 250 and 500 μg/ml respectively. All the synthesized Schiff bases have shown good activity against the tested microbes. The structure activity relationship showed that increased antimicrobial activity was observed when nitro group was present at p-position in the arylidene unit44.
Thiosemicarbazone and 4-thiazolidinone derivatives were synthesized in one and two step, respectively, from thiosemicarbazide, in satisfactory yields. The synthesized compounds were evaluated against host cells infected with Toxoplasma gondii. The study showed that thiosemicarbazones and 4-thiazolidinone derivatives were effective against intracellular T. gondii45.
Some new 2-Imino-3-[carboxamido-p-hydroxyphenyl]-5-arylidene-4-thiazolidinone, unsubstituted or carrying hydroxy, nitro and chloro groups on the benzene ring, were synthesized and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria and fungi by the cup-plate method. The 5-arylidene derivatives showed an antibacterial efficacy considerably greater than that of the parent 2-imino-3-(carboxamido p-hydroxyphenyl)-thiazolidine-4-one, suggesting that the substituted and unsubstituted 5-arylidene moiety plays an important role in enhancing the antimicrobial properties of this class of compounds46.
Some new derivatives of 3-allyl-1,3-thiazolidin-4-one were synthesized and antimicrobial activity was tested in vitro in Mueller-Hinton agar against standard bacteria cultures S. aureus, E. faecalis, E. coli, P. aeruginosa, K. pneumoniae, P. mirabilis, B. subtilis and B. cereus and standard fungal culture C.albicans. The results of microbial activity showed that all the compounds could be characterized as antimicrobial and antifungal agents. None of the tested compounds showed activity against P. aeruginosa. The compounds with the nitro group in their structure showed a higher antimicrobial and antifungal activity47.
N-(2-aryl-4-oxothiazolidin-3-yl)-2-(5-(phenoxymethyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl) acetamide were prepared and evaluated for their antibacterial and antifungal activities. The antibacterial activities of all the compounds were studied against S. aureus, B. subtilis, E. coli, and K. promioe at a concentration of 50μg/mL by agar cup plate method. The fungicidal activity of all the compounds was studied at 1000ppm concentration in vitro. Plant pathogenic organisms used were Nigrospora Sp, A. niger, B. thiobromine and R. nigricum, F. oxyporium. The antifungal activities of all the compounds were measured on each of these plant pathogenic strains on a potato dextrose agar medium48.
3-Hydroxy-N-(4-oxo-2-arylthiazolidin-3-yl)-benzofuran-2-carboxamide were prepared and evaluated for their antibacterial and antifungal activities. The antibacterial activities of all the compounds were studied against S. aureus, B. subtilis, E. coli and K. promioe at a concentration of 50μg/mL by agar cup plate method. The fungicidal activity of all the compounds was studied at 1000ppm concentration in vitro. Plant pathogenic organisms used were Nigrospora Sp, A. niger, B. thiobromine, R. nigricum, F. oxyporium. The antifungal activities of all the compounds were measured on each of these plant pathogenic strains on a potato dextrose agar (PDA) medium49.
A series of 4-oxo-thiazolidine derivatives have been obtained by cyclisation of various Schiff’s base with thiomalic acid. The compounds were screened for their in vitro antibacterial activity using cup-plate agar diffusion method at a concentration of 40μg/ml using gram positive bacterial strains such as S. aureus and gram negative bacterial strain such as E. coli. Substitution of -OCH3 group increases the antibacterial activity as compared to non substituted phenyl ring, where as unsaturation also increases the activity. These are all electron releasing substituents. The introduction of a methoxy group at position no. 4 or 5-oxothiazolidine increases anti bacterial activity particularly against S. aureus50.
A new series of 1,3-benzothiazol-2-yl-1,3-thiazolan-4-one has been synthesized and were evaluated for their antibacterial activity against Gram-positive bacteria viz. B. subtilis, B. sphaericus, S. aureus and Gram-negative bacteria viz. P. aeruginosa, K. aerogenes, C. violaceum. Amongst them, compounds containing [(4-chlorophenyl)methylidene] moiety, [(3-nitrophenyl) methylidene] moiety and [(2-thienyl)methylidene] moiety showed significant antibacterial activity, almost equal/more than the activity of the standard drug Streptomycin. Further, the compounds were also screened for their antifungal activity against C. albicans, A. fumigatus, T. rubrum and T. mentagrophytes. Most of these new compounds showed appreciable activity against test bacteria and fungi51.
A new series N-(2-(4-substituted phenyl)-4-oxothiazolidin-3-yl)isonicotin-amide derivatives were synthesized by the reaction of Schiff base (isoniazid and substituted benzaldehyde) with mercaptoacetic acid. The synthesized compounds showed good antibacterial activity against S. aureus and E. coli. It showed that the compound had mild activity both towards gram +ve and gram –ve organism52.
A novel series of 2-(3,5-dimethyl-1-phenyl-1H-4-pyrazolyl)-3-(aryl/heteroaryl)-1,3-thiazolidin-4-one derivatives has been synthesized readily in one-pot from 3,5-dimethyl-1-phenyl-1H-4-pyrazolecarbaldehyde and were screened for antibacterial activity against B. subtilis, Staphylococcus aureus, Escherichia coli and Staphylococcus pyogenes. Amongst them, compounds containing pyridyl and pyrimidinyl moiety exerted superior antibacterial activity against S. aureus and E.coli at the concentration of 6.25μg/mL. Therefore the presence of pyridyl group on nitrogen of thiazolidinone ring and the presence of pirimidinyl ring might be the reason for the significant inhibitory activity53.
4-Thiazolidinones have been prepared by the reaction of various substituted schiff bases with mercapto acetic acid. The antibacterial activity of the compounds has also been screened against B. subtillis, S. aureus, E. coli and P. aeruginosa. Some of the tested compounds were shown significant activities against gram positive and gram negative bacteria54.
A series of 5-arylidene derivatives of N-(2-(4-chlorophenyl)-4-oxothiazolidin-3-yl) isonicotinamide have been synthesized using different types of substituted benzaldehyde and all synthesized compounds were screened for antibacterial and antifungal activities using the turbidimetric method. Turbidity produced is measured by taking absorbance and compared with turbidity produced by standard drug. The compounds were screened against E. Coli, B. Subtilis and S. Aureus for antibacterial activity and against Aspergillus niger, Candida albicans, S.cereviceaes for antifungal activity. Antibacterial screening revealed that compounds exhibit moderate activity as compared to standard. Antifungal screening revealed that compounds exhibit moderate activity as compared to standard55.
Synthesis and in vitro antimicrobial evaluation of 5‐arylidine derivatives of 2‐(3,4, 5‐trimethoxyphenyl) ‐3‐(4‐phenylthiazol‐2‐yl)thiazolidin‐4‐one were carried out. All the synthesized compounds were evaluated for their in vitro antibacterial activity against gram +ve and gram ‐ve bacterial strains viz, Escherichia coli, Staphylococcus aereus, Klebeliessa pneumoniae and Pseudomonas areginosa by using the agar well diffusion method. The compounds showed some interesting antibacterial activity. The substitution of 5‐arylidne groups on new thiazolidinone have resulted enhanced antibacterial activity. The compounds showed moderate antifungal activity in a scattered manner. In vitro antifungal assays of all the synthesized compounds were performed against fungal strains Aspergillus niger and Aspergillus flavus using agar well diffusion method. However, subsequent introduction of different arylidine group at position 5 has resulted in enhanced activity of 4‐thiazilidinone. Among the 5‐benzylidine derivatives, the benzyl group having substitution at para position has shown to be more active than the ortho substituted derivatives56.
The synthesis of 4-thiazolidinones has been prepared by the condensation of Schiff’s bases from p-cumidine and aryl aldehydes with thioglycolic and thiolactic acid. The products have been screened for antimicrobial activity57.
Some new 1-[{2´-(3˝-2˝-oxo-4˝-substitutedaryl-1˝-azetidinyl)-1´,3´-thiazol-4´-yl}-amino-2-phenyl-4-cyclohexylideneimidazol]-5-one and 1-[{2´-(2˝-substitutedaryl-4˝-thiazolidinon-3˝-yl)-1´,3´-thiazol-4´-yl}-amino-2-phenyl-4-cyclohexylideneimidazol]-5-one have been synthesized. All these compounds were screened in vitro for their antibacterial ctivity against various strains of bacteria. Compound showed superior antibacterial activity against Klebsiella pneumoniae. Structure activity relationship of these compounds revealed that conversion of different benzylidenes in to their corresponding azetidinone congers and thiazolidinone congers markedly enhanced the antibacterial activity. Compound with a phenyl group having methoxy group at para position show promising antibacterial activity. Compound bearing β-lactam rings possessed better antibacterial activity corresponding to thiazolidinones58.
A series of 2-(substituted phenyl)-3-[3-(2-oxo-2H-chromen-3-yl)-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]-1,3-thiazolidin-4-ones were synthesized and evaluated for their antimicrobial activity. The synthesized compounds were screened for their antibacterial activity against Gram positive S. aureus and Gram negative E. coli strains and antifungal activity against C. albicans by cup-plate method and agar diffusion method. The test compounds and standards were evaluated at 100 μg/mL concentration. Thus it was concluded that the compounds without substitution and with Cl substitution showed the highest activity against S. aureus and the compounds without substitution showed the highest activity against E. coli. The compounds with OCH3, N(CH3)2, NO2, and Cl substitution and unsubstituted showed the highest activity against C. albicans59.
2-(4-substituted phenyl)-3-(4-substituted phenyl)-5-methylthiazolidin-4-ones were synthesized by condensing 4-substituted anilines with 4-substituted benzaldehydes by using ethanol as solvent. The compounds were screened for antibacterial and antifungal activity. The antibacterial activity conducted against Staphylococcus aureus and Escherichia coli using Ampicillin and Penicillin-G as a reference standard. The results revealed that the test compounds exhibits remarkable antibacterial activity60.
Several 2‐azetidinones and 4‐thiazolidinones have been synthesized from halo substituted Schiff bases using conventional as well as microwave technique. All compounds screened for antimicrobial activity against Bacillus subtilis, Escherichia coli, Aspergillus niger and Aspergillus flavus. Results show that presence of halogen with methoxy substituent in basic 2‐azetidinones and 4‐thiazolidinone nucleus exhibits potent antimicrobial activity against various pathogens61.
A new series of 2-(2–hydroxyl-5-(substituted phenyldiazyl)-N-[(4-oxo-2-phenylquinazoline 3(4H)–yl)]-4-oxo-1,3-thiazolidine-1-carbothioamide have been synthesized by the reaction of substituted thiosemicarbazones with thioglycolic acid in presence of zinc chloride in DMF. The antimicrobial activities of the synthesized compounds were screened in vitro using the Disc Diffusion technique against bacterial and fungal pathogens Escherichia coli, Salmonella typhimurium, Klebisiella pneumoniae and Aspergillus niger, Aspergillus fumigatus, Curvularia lunata strains at 600μg/ml. Compounds with p-nitro substitution enhanced the antimicrobial profile. (ii) p-methoxy substituent in aryl ring showed poor antimicrobial activity. (iii) p-nitro group showed higher antimicrobial activity than p-chloro and p- methoxy derivatives62.
3-allyl-2-sulfanylamido-4-thiazolidinones have been synthesized after substitution of amino group of sulfanylamide with allylisothiocyanate and cyclization into 4-thiazolidinones. The synthesized compounds were tested for their antibacterial and antifungal activity (MIC) in vitro against microorganisms: S. aureus, E. faecalis, E. coli, P. aeruginosa, K. pneumoniae, P. mirabilis, B. subtilis, B. cereus and C. albicans taking sulfadimidine, sulfathiazole, sulfanilamide and sulfamethizole as standard drugs. Synthesized compounds demonstrated selective activity against B. cereus63.
Antimicrobial activity of the new compounds was tested in vitro against bacterial cultures–Staphylococcus aureus, Escherichia coli, Bacillus sutilis, Klebsiella pneumoniae–and fungal cultures–Candida albicans, Candida glabrata, Candida krusei, Candida kefyr, Candida tropicalis and Candida parapsilosis. Microbiological analysis showed that all new thiazolidinone derivatives with nitronaphthylamine substituent possessed antibacterial and antifungal properties. The results indicate that naphthylamine derivatives having a thiazolidinone and especially nitrofuryl fragment in one molecule could be potential antimicrobial compounds64.
The synthesis of three series of compounds, namely, ethyl 2-((Z)-5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-2,4-dioxothiazolidin-3-yl)acetates, methyl-2-((Z)-5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-2, 4-dioxothiazolidin-3-yl)acetates, and 2-((Z)-5-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-2, 4-dioxothiazolidin-3-yl)acetic acids were carried out and tested for their in vitro antibacterial and antifungal activity. Antimicrobial evaluation of the compounds has shown that some of the compounds are associated with remarkable antifungal activity65.
A number of derivatives of 2-(substituted phenyl)-3-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl) thiazolidin-4-one have been synthesized from the reaction of 4-(6-methylbenzo[d]thiazol-2-yl)benzenamine, with different substituted benzaldehydes, followed by cyclocondensation reaction of the prepared imines with 2-meraptoacetic acid in high yields. Thiazolidin-4-one derivatives were evaluated for their antibacterial activity against Escherichia coli as gram negative and Staphylococcus aureus as gram positive, the results have shown signifcant activity against both types of bacteria66.
In view of potential antibacterial activities of thiazolidine-4-one derivative were prepared by schiffs base technique. The compounds were screened by antibacterial activity, thiazolidine-4-one also showed antifungal activity67.
A novel series of Schiff bases and 4-thiazolidinones have been prepared from the building blocks 2-chloro pyridine-3-carboxylic acid and 2-amino-6-ethoxy-benzothiazole. The synthesized compounds were screened for their antimicrobial activity. Some compounds revealed significant antibacterial activity against Escherichia coli. On the other hand, few of the tested compounds revealed potent antifungal activity against Candida albicans. Overall observation from the results of the antimicrobial activity of the synthesized compounds revealed that compounds containing –Cl, –NO2 group and furan nucleus are more active than the remaining compounds68.
A one-pot, three-component, microwave irradiated and conventional solution-phase synthesis of bioactive venlafaxine analogs such as 2,3-disubstituted-1,3-thiazolidin-4-ones under mild conditions are reported. All the synthesized compounds were screened for their efficacy as antimicrobials in vitro by the disk diffusion and microdilution method against pathogenic strains such as Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens, Xanthomonas campestris pvs, Xanthomonas oryzae, Aspergillus niger, Aspergillus flavus, Fusarium oxysporum, and Fusarium monaliforme species. Among these compounds some of them showed potent antimicrobial activity, when compared to standard drug69.
An elegant microwave assisted environmentally benign approach to the synthesis of novel 3’- [4’-N-{4-methyl-2-pyrimidinyl}-benzenesuphonamido]-spiro-(3H-indol-3,2’-thiazolidin)-1H-2,4’ (5H) dione and their Mannich’s bases has been described. Mannich’s bases of sulphamerazinyl substituted [spiro-indolo-4-thiazolidinone] were screened for their in-vitro antimicrobial activities against bacterial species (E. coli and B. substilis) and fungal species (A. niger and A. flavus) by Agar-well assay method against the standard drugs70.
A series of novel thiazolidinones have been synthesized by reaction of various Schiff bases of coumarin with thioglycolic acid. Various Schiff bases of coumarin were synthesized by condensation of 4-[(4-aminophenyl)amino]-2H-chromen-2-one with different aldehydes. The thiazolidinone derivatives were evaluated for their anti bacterial and antifungal activity by broth dilution method. Most of the compounds were more active against E. coli, S. aureus and B. subtilis. Most of the compounds demonstrated antifungal activity for C. albicans similar to that of Griseofulvin, found less active than other fungal specie (A. niger)71.
2,3-disubstituted-5-[(4'-methoxy)benzylidene]-4-thiazolidinones derivatives were prepared and tested against Gram-positive (S. aureus and S. pyogeneus) and Gram-negative (P. aeruginosa and E. coli) bacteria, as well as antifungal activity against C. albicans, A. niger and A. clavatus by broth dilution method. From the results of antibacterial and antifungal activity; it can be concluded that the compounds bearing -OH, -OCH3 and -Cl group are more potent than the remaining compounds72.
A new series of 2-hydrazone-thiazoline-4-ones and 2-hydrazone-5-arylidene-thiazoline-4-ones were synthesized starting from various thiosemicarbazones by the Hantzsch condensation with chloroacetic acid. The newly synthesized compounds were screened against: Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and one fungal strain: Candida albicans. The compounds demonstrated a good inhibitory activity against E. coli. The results of the antifungal screening showed that the 2-hydrazon-thiazolin-4-ones presented an excellent activity against Candida albicans. None of the compounds inhibited the growth of Pseudomonas aeruginosa and Bacillus subtilis. The activity against S. aureus was also moderate. In the case of the presence of p-bromobenzylidene or 4-hydroxy-benzylidene fragments in the 5-position of thiazolin-4-one ring cancels the activity against Candida albicans. In addition, the presence of thiazole ring in the structure didn't show to be favorable for the activity against the bacterial strains used in this study. On the other hand, the activity against C. albicans was increased by the presence of the thiazole ring73.
Schiff base, azetidinone and 4-thiazolidinone derivatives of para aminosalicylic acid were synthesised. It was planned to employ the structure based computer aided drug designing (CADD) to Schiff base, azetidinone and 4-thiazolidinone of para aminosalicylic acid. the novel molecules were synthesised and evaluated for antimicrobial studies. The synthesised compounds were screened for their in vitro antimicrobial activity74.
Some 2-aryl-3-(substituted benzothiazolyl)-1,3-thiazolidine-4-ones have been synthesized. All the newly synthesized compounds were screened for antibacterial activity at a concentration of 200 μg/mL and 100 μg/mL using DMF as a control and Streptomycin and Ceftazidime used as standard against gram positive and gram negative bacteria. Among the synthesized compound some of them possess good activity. However, the activities of the tested compounds are much less than those of standard antibacterial agents used75.
CONCLUSION:
This review has highlighted the different derivatives of 4-thiazolidinones responsible for its potential antimicrobial activities. The literature reveals that 4-thiazolidinone has diverse biological potential and the simple synthetic routes for synthesis have taken much attention over the years for the chemists, pharmacologists and young researchers. The 4-thiazolidinone derivatives have shown significant antimicrobial activity against wide variety of microorganisms such as gram positive, gram negative bacteria and fungi. Thus this paper proves to be significant for further research work on the bioactive 4-thiazolidinone nucleus for the development of newer antimicrobial agents.
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Received on 02.02.2014 Modified on 05.03.2014
Accepted on 12.03.2014 © AJRC All right reserved
Asian J. Research Chem. 7(4): April 2014; Page 446-457