875-97-8

Basic information

• Product Name: 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate
• Synonyms: 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate;(2,4-dioxo-1,3-thiazolidin-5-yl)acetic acid(SALTDATA: FREE);2-(2,4-Dioxo-1,3-thiazolidin-5-yl)aceticacid
• CAS NO: 875-97-8
• Molecular Formula: C₅H₅NO₄S
• Molecular Weight: 175.16
• Mol File: 875-97-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 489.3°C at 760 mmHg
• Flash Point: 249.7°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 6.51E-11mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate(875-97-8)
• EPA Substance Registry System: 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate(875-97-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 875-97-8(Hazardous Substances Data)

Usage

General Description

2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate is a chemical compound with the molecular formula C6H7NO4S. It is an ester derivative of the amino acid cysteine and is commonly used in the synthesis of pharmaceuticals and agrochemicals. 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate has a thiazolidine ring structure and is known for its potential pharmacological activities, including antidiabetic and anti-inflammatory properties. It is also utilized as a reagent in organic chemistry, particularly in the formation of various bioactive compounds. Its unique structure and reactivity make it a valuable building block in the development of novel drugs 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 articles and documents

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.

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.

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