875-97-8

Usage

Uses

Used in Pharmaceutical Synthesis:
2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of drugs with potential antidiabetic and anti-inflammatory properties.
Used in Agrochemical Production:
In the agrochemical industry, 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate is used as a precursor in the production of agrochemicals, leveraging its reactivity and structural features to create compounds with pesticidal or herbicidal activities.
Used as a Reagent in Organic Chemistry:
2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate serves as a reagent in organic chemistry, particularly for the formation of various bioactive compounds, due to its unique structure and reactivity that facilitate the creation of novel drug candidates and biologically active molecules.

InChI:InChI=1/C5H5NO4S/c7-3(8)1-2-4(9)6-5(10)11-2/h2H,1H2,(H,7,8)(H,6,9,10)

Upstream product

• 5374-29-8 (2,4-dioxo-thiazolidin-5-ylidene)-acetic acid 
• 590-28-3 potassium cyanate 
• 70-49-5 DL-thiomalic acid 
• 108-31-6 maleic anhydride 
• 17356-08-0 thiourea 
• 33176-41-9 2-imino-2,3,4,5-tetrahydro-4-oxo-1,3-thiazol-5-acetic acid 

Downstream Products

• 5374-29-8 (2,4-dioxo-thiazolidin-5-ylidene)-acetic acid 
• 51226-17-6 2-(2,4-dioxothiazolidin-5-yl)acetic acid chloride 
• 1293365-89-5 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-90-8 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-chlorophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-91-9 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-bromophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-92-0 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-fluorophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-93-1 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-2-chlorophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-94-2 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-methylphenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-95-3 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-3-methoxyphenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-96-4 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-4-methoxyphenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-97-5 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-(-3,4-dimethoxyphenyl)-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-98-6 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-(-3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl)acetamide 
• 1293365-99-7 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-2-nitrophenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1293366-00-3 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-(5-3-nitrophenyl-1,3,4-thiadiazol-2-yl)acetamide 

Relevant academic research and scientific papers

Pyrimidine-thiazolidinone derivatives

Pyrimidine-thiazolidinone derivatives may be used for preventing or treating diseases in humans or animals, and have demonstrated efficacy specifically in treating type-2 diabetes. Methods of synthesizing the pyrimidine-thiazolidinone derivatives, described herein, can provide high yields in a short time and with high purity. The pyrimidine-thiazolidinone derivatives demonstrate improved hypoglycemic activity compared to most anti-diabetic drugs currently available.

Synthesis and in vitro antiproliferative and antibacterial activity of new thiazolidine-2,4-dione derivatives

In our present research, we synthesised new thiazolidine-2,4-diones (12–28). All the newly synthesised compounds were evaluated for antiproliferative and antibacterial activity. Antiproliferative evaluation was carried out using normal human skin fibroblasts and tumour cell lines: A549, HepG2, and MCF-7. The IC50 values were determined for tested compounds revealing antiproliferative activity. Moreover, safety index (SI) was calculated. Among all tested derivatives, the compound 18 revealed the highest antiproliferative activity against human lung, breast, and liver cancer cells. More importantly, the derivative 18 showed meaningfully lower IC50 values when compared to the reference substance, irinotecan, and relatively high SI values. Moreover, newly synthesised compounds were screened for the bacteria growth inhibition in vitro. According to our screening results, most active compound was the derivative 18 against Gram-positive bacteria. Therefore, it may be implied that the novel compound 18 appears to be a very promising agent for anticancer treatment.

Novel thiazolidinedione-5-acetic-acid-peptide hybrid derivatives as potent antidiabetic and cardioprotective agents

Thiazolidinediones (TZDs) are one of the important clinically established antidiabetic agents. Amino-acid and peptides have an advantage of better target selectivity and specificity. As hybrids, they also improved absorption and showed better bioavailability, which in turn makes them safer. Hence, here an effort has been made to synthesize hybrids of thiazolidinedione with amino-acids and peptides and evaluate their antidiabetic and cardioprotective effect in streptozotocin-nicotinamide (STZ-NA) induced Type 2 diabetes mellitus (T2DM) rat models. A series of 14 thiazolidinedione-5-acetic acid hybrids with of different amino-acids and peptide combinations were synthesized, characterized and further screened for antidiabetic and cardioprotective activity. Among all, six compounds T1 (SSDMA1), T4 (SSDMA4), T5 (SSDMA5), T7 (SDMA13), T9 (SSDMA15) and T13 (SSDMA49) showed better antioxidant activity and comparable % glucose uptake by yeast cells. Hence, the in vivo antidiabetic screening was done for these six compounds. Among all six T1, T7, T13 showed significant blood glucose level decrease compared to standard pioglitazone HCl. Also T1, T7 and T13 showed better antioxidant activity with lower IC50 value than standard ascorbic acid, and hence in vivo cardioprotective studies were done for these. The ECG studies showed that T1 (SSDMA1) and T7 (SSDMA13) were better effective than SDMA49 (T13) in restoring the normal functioning of the heart, thus may help in preventing the development of diabetic cardiomyopathy (DCM) and controlling T2DM.

Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds

A series of novel N-(4-aryl-1,3-thiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin- 5-yl)acetamides (4a-k) and N-(1,3-benzothiazol-2-yl)-2-(2,4-dioxo-1,3- thiazolidin-5-yl)acetamide derivatives (4l-o) are synthesized and evaluated for their anti-inflammatory and antioxidant activity (DPPH radical scavenging, superoxide anion scavenging, lipid peroxide inhibition, erythrocyte hemolytic inhibition). Compounds 4k and 4l have exhibited good antioxidant activity in four assays, while compounds 4c, 4d , 4m, 4n and 4o have shown good DPPH radical scavenging efficacy. Compounds 4a, 4h , 4i, 4k, 4m and 4n have possessed excellent anti-inflammatory activity. N-[4-(o-methoxyphenyl)-1,3-thiazol-2-yl]- 2-(2,4-dioxo-1,3-thiazolidin-5-yl) acetamide (4k) and N-(6-nitro-/methoxy-1,3- benzothiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide (4m and 4n) have exhibited both antioxidant and anti-inflammatory activities.

Synthesis and antihyperglycemic evaluation of new 2,4-thiazolidinediones having biodynamic aryl sulfonylurea moieties

New 2,4-thiazolidinediones with aryl sulfonylurea moieties 8a-h have been synthesized by condensing various substituted sulfonamides and 5-(isocyanatomethyl) thiazolidino-2,4-dione 6. The isocyanomethyl thiazolidinedione was obtained by using the Curtius

New thiazolidinedione-5-acetic acid amide derivatives: Synthesis, characterization and investigation of antimicrobial and cytotoxic properties

The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione- 5-acetic acid amides 3a-n. The structures of the compounds were confirmed by IR, 1H, 13C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC50 values of 33, 35, 30 and 36 μM, respectively. Springer Science+Business Media, LLC 2011.

Synthesis of new potential anticancer agents based on 4-thiazolidinone and oleanane scaffolds

The synthesis and evaluation of the anticancer activity of new acylated oximes derivatives of oleanolic acid with 4-thiazolidinone-3(5)-carboxylic acid moieties were described. Newly synthesized compounds were elucidated on the basis of elemental analyses

Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives

The synthesis and evaluation of anticancer activity of 2,4-thia(imida)zolidinedione-3- and 5-acetic acids amides were described. The structures of compounds were determined by IR, 1H NMR, and MS analysis. In vitro anticancer activity of these compounds has been tested in National Cancer Institute (NCI) and the relationships between structure and anticancer activity are discussed. Among 2,4-azolidinedione-acetic acids derivatives 2-[5-(4-chlorobenzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide (Ic) was superior to other related compounds in terms of high selectivity for the leukemia CCRF-CEM (log GI50 = -6.06), HL-60(TB) (log GI50 = -6.53), MOLT-4 (log GI50 = -6.52) and SR (log GI50 = -6.51) cell lines.