Abstract
Thiazolidinone scaffold has become a highly powerful scaffold in the current era when it comes to its clinical importance. Its wide variety of biological functions have piqued the researchers’ intense curiosity. The 1,3-thiazolidin-4-ones have numerous pharmacological properties, including anti-cancer, anti-diabetic, anti-microbial, antiviral, anti-inflammatory and anticonvulsant properties because of these wide spectrum biological properties. Thiazolidinones are called as molecule of magic. In the recent years, a number of innovative synthetic techniques have been developed to create a variety of scaffolds to investigate a range of biological activities. Numerous researchers have been drawn to this skeleton by the variety in the biological response profile to investigate its potential against various activities.
Keywords
- thiazolidinones
- synthesis
- biological activities
- thiazolidinone scaffold
- pharmacological properties
1. Introduction
Heterocyclic compounds play an important role in organic chemistry and of supreme practical and theoretical consequence. Therefore, more research being done on heterocyclic compound in chemistry. Heterocyclic compounds have an important role in therapeutic agents, drugs, dye stuffs etc. Therefore heterocyclic compound has taken a prominent place in the field of chemistry. Heterocyclic compounds retain the key to improve the quality of human life for example; more than 70% of the medications (or) drug used today is heterocyclic compounds. These are widely available in nature and act as key intermediates in biological processes. Over the years, chemists have paid close attention to a variety of physiologically active compounds that contain heteroatoms including nitrogen, sulphur, and oxygen because of their significance to biology. Thiazolidinone is considered as indispensable anchor for development of new therapeutic agents because this five member magic moiety possesses all types biological activities. Thus the thiazolidinone nucleus has been studied in the field of organic, medicinal and photochemistry. There are many examples of biologically active such as antibiofilm [1, 2], hypoglycemic [3], antimicrobial [4], analgesic [5], antipyretic [6] and anti-inflammatory activities [7, 8] anticonvulsant [9], antihistaminic [10], anti HIV [11] cardio protective [12], antinociceptive [13] With a sulphur atom at position 1, a nitrogen atom at position 3, and a carbonyl group at position 2, 4, or 5, thiazolidinones are thiazolidine derivatives. However, its derivatives are among the most researched moieties, and the discovery of its existence in penicillin was the first indication that it existed in nature. Similar to 1,3-thiazolidin-4-ones, which are heterocyclic nuclei with a sulphur atom at position 1, a nitrogen atom at position 3, and a carbonyl group at position 4, they have been the focus of substantial research recently. Since it is so adaptable that the 4- thiazolidinone scaffold has been used in a number of clinically effective medications. They have been used anti-HIV, anti-tubercular, anti-microbial, anti-inflammatory and anti-viral medicines. The presence of arylazo, sulfamoylphenyl or phenylhydrazone moiety at various postions of the thiazolidone ring has been extensively reported to enhance anti-microbial activity. Its antibacterial activity may be caused by its inhibitory activity of enzyme Mur B, which is a precursor acting during the biosynthesis of peptidoglycan. Numerous publications highlighting their chemistry and pharmacological uses have been published in the literature. Thiazolidinone possess wide range of biological actions from antibacterial to anticancer. Various recent new drug developments of thiazolidinone derivatives show better effect and less toxicity. Moreover the possible improvements in the activity can be achieved by slight modifications in the substituent on the thiazolidinone nucleus. This has been noticed so far, that the introduction of another heterocyclic moiety into the thiazolidinone nuclei will enhance the biological activities.
Recently, thiazole and thiazolidinone derivative have been used as a potent antitrypanosomal agents [14]. Therfore in this chapter it is planned to discuss the synthesis of various thiazolidinone derivatives in brief and their widespectrum bilogical activities will be discussed elaborately.
2. Synthesis
In the literature, a variety of techniques for creating 4-thiazolidinones have been extensively described. An amine, a carbonyl molecule, and a mercapto-acid are the three elements that are often used in the main synthesis pathways for 1,3-thiazolidin-4. The disclosed classical synthesis can be either a two-step method or a one-pot, three-component condensation (Figure 1). The first step in the reactions is the creation of an imine (the nitrogen of the amine attacks the carbonyl of the aldehyde or ketone). This is followed by intramolecular cyclization on the removal of water.
The most common method for making 4-thiazolidinone derivatives is syntheic [15]. On being treated with mercaptoacetic acid while having silica chloride present as a heterogeneous catalyst to speed up the intramolecular cyclocondensation in a solvent-free environment, a variety of quinazolinyl azomethines produce 4-thiazolidinones (Figure 2).
By using benzylidene-anilines and mercaptoacetic acid in benzene at 30 C for 10 min, Bolognese et al. [16] produced a variety of 1,3-thiazolidin-4-one derivatives. Following chromatographic purification, the 1,3-thiazolidin-4-ones are extracted at a yield of 65–90% (Figure 3).
A solvent-free, nano-titania-supported sulfonic acid [nano-TiO2- SO3H (n-TSA)] catalysed method has been developed by Ruby Singh et al. [17]. for the synthesis of novel hybrids of isoxazolyl-spiro-thiazolidinones that are promising for use in pharmaceuticals (Figure 4).
To create a few thiazolidinone derivatives using the recommended techniques to look into their potential antiamoebic effect as described in a three step reaction process for obtaining target chemicals (Figure 5). In the first stage, 2-methylpropan-1-amine and phenylisothiocyanate were combined with toluene to create 1-(2-methylpropyl)-3 phenylthiourea. The second stage was the cyclization of 3-(2-methylpropyl)-2-(phenylimino)- 1,3-thiazolidin-4-one with the use of sodium acetate and chloroacetic acid. In the third stage, 3-(2-methylpropyl)-2-(phenylimino)-1,3-thiazolidin-4-one was Knoevenagel condensation with various substituted aldehydes in ethanol to produce the target compounds [18].
Another method involves employing dialkyl substituted bromoacetic acid or bromacetyl chloride as the starting material to create 5-substituted dialkyl thiazolidinones. In order to produce the intermediate, which was then hydrolyzed to produce 5,5-dialkyl- thiazolidin-2,4-dione, the reaction begins with the refluxing of dialkyl substituted bromoacetic acid or bromoacetyl chloride with thiourea in the presence of sodium acetate in ethanol (Figure 6) [19].
By refluxing the mixture of substituted benzaldehyde
By reacting 4-hydrazinobenzenesulfonamide hydrochloride with 4-substituted aldehydes in the presence of sodium acetate in ethanol, followed by the reaction of the resulting phenyl hydrazones with excess thiolactic acid at 60°C for 3 h, Abdellatif et al. [21], were able to produce 2,4,5-trisubstituted thiazolidinone derivatives, as shown in (Figure 8).
Velmurugan. V et al. [22] have been synthesized Thiazolidinone derivatives from thiourea (Figure 9).
Novel oxazinyl thiazolidinone compounds have been created by Rajalakshmi et al. [23], as powerful antidiabetic agents (Figure 10).
Novel Thiazinyl-thiazolidinone compounds have been created by Rajalakshmi et al. [24], as potential in vitro anti-diabetic and antioxidant agents (Figure 11).
Substituted benzaldehyde/acetophenone were reacted with thiosemicarbazide in HCl to get the intermediate schiffbase. Schiff base intermediate react with chloro acetic acid and sodium acetate in acetic acid to obtain 4-thiazolidinone analogs by Rahim et al. [25]. Saiz et al. [26] have been synthesized 2-hydrazolyl-4- thiazolidinones by the reaction involving aldehydes, thiosemicarbazides, and maleic anhydride, effectively assisted by microwave irradiation (Figure 12).
Benmohammed et al. [27] a series of reaction involving thiosemicarbazones react with ethyl 2-bromoacetate in anhydrous sodium acetate afforded to the thiazolidin-4-one derivatives (Figure 13).
Ottana et al. [28] has been reported the series of new thiazolidinone derivatives by reacting
One pot three component synthesis containing aldehyde, thiourea and chloroform to give 2-amino-4-thiazolidinone derivatives (Figure 15) reported. Various imino thiazolidinones were developed by using different reagents with different reaction conditions by Jieping et al. [29].
Pang et al. [30] were synthesized by the Mesoporous MCM-41 supported Schiff base and CuSO4.5H2O mediated in the cyclocondensation of mercaptoacetic acid with imines (or aldehydes and amines) to afford thiazolidinone derivatives (Figure 16).
2.1 The Bioimplication of Thiazolidinones
Thiazolidinones are the primary compounds with a diverse range of biological activity. This ring handles several pharmacological processes. Thiazolidinones are being studied biologically using a variety of mechanisms, including receptor-mediated mechanisms and enzymatic activity. The biological study of thiazolidinones has shown that substitution at positions 2, 3, and 5 imparts various activity. As seen in Figure 17, many commercial medications that contain the thiazolidinone scaffold exhibit a variety of biological actions.
2.2 Antibacterial and antifungal activity
Veerasamy et al. [31] have prepared a series of 1,3-thiazolidin-4-one derivatives
Different levels of inhibition against bacteria and fungus are present in thiazolidinones with substituted positions at C-2 and N-3. Multi-drug resistance microbial infections have rapidly increased in frequency during the past few decades, posing a serious health risk. Nearly every location of the 4-thiazolidinone has been investigated in an effort to increase its antibacterial and antifungal activities. Thiazolidinone derivatives’ SAR analyses revealed that they are more efficient against gram-negative bacteria than gram-positive bacteria. Therefore, finding novel antimicrobial drugs will continue to be a difficult and vital work for medicinal chemists. According to Liesen et al., 4-thiazolidinone compounds made from ethyl (5-methyl-1-H-imidazole-4-carboxylate). The entire produced chemicals were tested for their antibacterial and antifungal activities against a variety of diseases. The findings demonstrated that, in comparison to common antibacterial and antifungal medications like
The kind of the substituents at the thiazolidinone ring’s C-2 and N-3 substantially influences antibacterial activity. Compound 51–3-(1,5-dimethyl-3-oxo-2-phenyl-2,3- dihydro-1H-pyrazol-4-yl) -2- \s(2-hydroxy-3,5-diiodophenyl) -thiazolidin-4-one (
Recently, a group of 2-thioxo-4-thiazolidinones and 4,40-bis(2-thioxo-4- thiazolidinone-3-yl)diphenylsulfone derivatives were synthesised by El-Gaby et al. The majority of the compounds were found to have moderate efficacy against the tested bacterial strain.
Bondock et al. [34]. created thirteen compounds and tested them against
Bonde et al. [35] reported the synthesis of
2.3 Antitubercular activity
Kucukguzel et al. [36]. reported substituted 4-thiazolidinones have antimycobacterial action, although only compounds (
The synthesis of N-pyridyl-N0 -thiazolylhydrazine derivatives was described by Zitouni et al. [37]. High antituberculosis activity was demonstrated by compound
2.4 Anticancer activity
A series of 2-arylthiazolidine-4-carboxylic acid amides were examined by Gududuru et al. for potential cytotoxic action against prostate cancer. With an IC50 of 0.55 lM and a 38- fold selectivity in
The primary cytotoxic activity of several 5-bromo-3-[(3-substituted-5-methyl-4- thiazolidinone-2-ylidene)hydrazono]-1H-2-indolinones (
Moorkoth et al. [39] have synthesized thiazolidinone
Kaminskyy et al. [40] have synthesized thiazolidinone derivatives these compounds were evaluated for their anticancer activity. Among the tested compounds, 3-(2,4-thiazolidinedione-5-ylidene)-carboxyimino]olean-12-en-28-oic acid methyl ester was superior to other related compounds with mean values of pGI50 = 5.51/5.57, pTGI = 5.09/5.13, and pLC50 = 4.62/4.64,low toxicity and moderate activity level in vivo hollowfiberassay. Zhou et al. have prepared a series of 2- thioxo-4-thiazolidinone derivatives
Sala et al. [41] have synthesized 2,3-thiazolidin-4-one
2.5 Anti-inflammtory and analgesic activity
Inflammation is a biological reaction to damage stimuli that is complicated and associated with numerous pathophysiological diseases. The short-lived free radical nitric oxide is one of the pro-inflammatory chemicals that are released by macrophages in response to inflammatory stimuli (NO). The commonly used nonsteroidal anti-inflammatory medicines naproxen and ibuprofen, which inhibit the COX enzyme that catalyses the manufacture of prostaglandins and tromboxane from arachidonic acid, are derived from arylalkanoic acids. These medications’ modes of action are linked to unpleasant side effects include renal and gastrointestinal toxicity. The anti-inflammatory and analgesic effectiveness of a new series of quinazolinone compounds with thiazolidinone at the second position was reported by Kumar et al. to combat the aforementioned side effects. Interestingly, compound
In their investigation of 3,30 -(1,2-ethanediyl)-bis[2-aryl-4- thiazolidinone] derivatives (
The ability of 2-aryl-3-[([1, 3, 4] thiadiazino [6,5-b]indol-3-ylamino]methyl] to reduce inflammation In order to study 1,3,4-thiadiazol-2-yl, 1,3-thiazolidin-4-one (
Vigorita et al. [47] have synthesized 3,3′-(1,2-Ethanediyl)-bis[2-aryl-4- thiazolidinone]
2.6 Anticonvulsant and antidepressant activity
Shiradkar et al. have created a brand-new series of clubbed thiazolidinone-barbituric acid (
2.7 Antiviral/anti-HIV activity
Different 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)- thiazolidin-4-ones were created by Chen et al. The analytical and spectral data of these newly synthesised chemicals supported their structures. The ability of these substances to inhibit HIV-RT was also tested. It was claimed that a high hydrophobicity value will have a significant impact on HIV-RT inhibitory efficacy. Compounds
HIV-RT inhibitory action in a group of 2-aryl-3-(4,5,6-trimethylpyrimidin-2-yl) thiazolidin-4-ones was negatively influenced by substitution at C-5 and positively affected by the addition of a chlorine atom on the phenyl at C-2. The anti-HIV-RT activity of compound 66 was remarkably strong (IC50 = 2.95 lM) [53].
Ravichandran et al. [54] have synthesized 1,3,4-thiazolidinone derivatives. The present 3D-QSAR study attempts to explore the structural requirements of thiazolidinone derivatives for anti-HIV activity. Based on the structures and biodata of previous thiazolidinone analogs,3D-QSAR studies have been performed with a training set consisting of 96 molecules, which resulted in two reliable computational models,
2.8 Antidiabetic activity
Compound
Liu et al. [57] studied a series of thiazolidinone-substituted biphenyl scaffold
Bhosle et al. [58, 59] have synthesized 2-hydrazolyl-4-thiazolidinone-5- carboxylic acids with pyrazolyl pharmacophore and evaluated for the antihyperglycemic activity in sucrose loaded rat model. Maccari et al. [59] have synthesized 5-arylidene-2-thioxo-4- thiazolidinones
3. Conclusion
In this chapter the various work up for the synthesis of biologically potent Thiazolidinone derifvatives are discussed and the wide spectrum biological activities are elaborated. The clinically utilised medications no longer have any of the 4-thiazolidinone nucleus’ efficacy. Although the four main clinical uses of title compounds are antibacterial, antitubercular, antiviral, and antidiabetic, other potential targets need to be investigated. The majority of locations were investigated to enhance the 4-thiazolidinone’s antibacterial and antitubercular profile, however none of the derivatives shown encouraging antitubercular activity. However, few derivatives of 4-thiazolinone with C-2 and N-3 substituted positions and the presence of electron-withdrawing substituent on the aromatic ring at C-2 position exibit varying degrees pharmacological activity. The clinically utilised medications no longer have any of the 4-thiazolidinone nucleus’ efficacy.
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