1010-53-3

Basic information

• Product Name: 3-phenylthiazolidine-2,4-dione
• Synonyms: 3-phenylthiazolidine-2,4-dione;3-PHENYL-2,4-THIAZOLIDINEDIONE;3-phenyl-1,3-thiazolidine-2,4-dione
• CAS NO: 1010-53-3
• Molecular Formula: C₉H₇NO₂S
• Molecular Weight: 193.22
• Mol File: 1010-53-3.mol

Chemical Properties

• Boiling Point: 315.1°Cat760mmHg
• Flash Point: 144.4°C
• Appearance: /
• Density: 1.416g/cm³
• Vapor Pressure: 0.000446mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-phenylthiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenylthiazolidine-2,4-dione(1010-53-3)
• EPA Substance Registry System: 3-phenylthiazolidine-2,4-dione(1010-53-3)

Safety Data

• Hazardous Substances Data: 1010-53-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylthiazolidine-2,4-dione is used as an oral antidiabetic medication for the treatment of type 2 diabetes. It functions by improving the body's insulin sensitivity, which aids in better glucose uptake and utilization, and by reducing glucose production in the liver.
Used in Research and Development:
3-Phenylthiazolidine-2,4-dione is utilized in scientific research for its potential anti-inflammatory and anti-cancer properties. Studies are conducted to explore its therapeutic potential in various conditions beyond diabetes, including inflammatory and neoplastic diseases.
However, it is important to note that the use of 3-phenylthiazolidine-2,4-dione is associated with several side effects, such as weight gain, fluid retention, and an increased risk of heart failure. These potential cardiovascular risks have led to controversy surrounding its use in the treatment of type 2 diabetes.

InChI:InChI=1/C9H7NO2S/c11-8-6-13-9(12)10(8)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 790-04-5 3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one 
• 102-15-8 phenylcarbamimidoylmercapto-acetic acid 
• 60-29-7 diethyl ether 
• 103-71-9 phenyl isocyanate 
• 68-11-1 mercaptoacetic acid 
• 103-72-0 phenyl isothiocyanate 
• 79-11-8 chloroacetic acid 
• 64-17-5 ethanol 
• 541-88-8 Chloroacetic anhydride 
• 3111-89-5 O-ethyl-N-phenylthiocarbamate 
• 3898-08-6 1,1-diphenylthiourea 
• 15076-85-4 [1,3]oxathiolane-2,5-dione 
• 34798-14-6 2-(2,2-dimethylhydrazono)-3-phenylthiazolidin-4-one 
• 60708-68-1 (4-oxo-3-phenyl-thiazolidin-2-ylidene)-phenyl-thiourea 

Downstream Products

• 42518-30-9 5-(Z)-benzo[1,3]dioxol-5-ylmethylene-3-phenyl-thiazolidine-2,4-dione 
• 2645-36-5 1-(N-phenylcarbamoyl)piperidine 
• 42518-30-9 3-phenyl-5-((Z)-piperonylidene)-thiazolidine-2,4-dione 
• 119714-05-5 5-[(3-ethyl-3H-benzoxazol-2-yliden)-ethylidene]-3-phenyl-thiazolidine-2,4-dione 
• 359648-41-2 5-(2-chloro-benzylidene)-3-phenyl-thiazolidine-2,4-dione 
• 99372-80-2 5-(3-nitro-benzylidene)-3-phenyl-thiazolidine-2,4-dione 
• 2718-82-3 5-[(3-ethyl-3H-benzothiazol-2-yliden)-ethylidene]-3-phenyl-thiazolidine-2,4-dione 
• 42518-27-4 5-Benzyliden-3-phenylthiazolidin-2,4-dion 
• 42518-24-1 5-(4-hydroxy-benzylidene)-3-phenyl-thiazolidine-2,4-dione 
• 101727-45-1 3-phenyl-5-salicylidene-thiazolidine-2,4-dione 
• 42518-29-6 5-cinnamylidene-3-phenyl-thiazolidine-2,4-dione 
• 25773-91-5 2-benzoyl-1-(2,4-dioxo-3-phenyl-thiazolidin-5-yl)-1,2-dihydro-isoquinoline 
• 39676-21-6 1-(2,4-dioxo-3-phenyl-thiazolidin-5-yl)-1H-isoquinoline-2-carboxylic acid diphenylamide 
• 4264-19-1 5-(2-methyl-benzoimidazol-1-ylmethyl)-3-phenyl-thiazolidine-2,4-dione 

Relevant articles and documents

Design, synthesis and biological evaluation of N-substituted indole-thiazolidinedione analogues as potential pancreatic lipase inhibitors

Pancreatic Lipase (PL) is a key enzyme responsible for the digestion of 50%–70% of dietary triglycerides, hence its inhibition is considered as a viable approach for the management of obesity. A series of indole-TZD hybrid analogues were synthesized, characterized and evaluated for their PL inhibitory activity. Knoevenagel condensation of various substituted indole-3-carboxaldehyde with substituted thiazolidinediones resulted in the formation of titled analogues. Analogues 6d and 6e exerted potent PL inhibitory activity (IC50-6.19 and 8.96?μM, respectively). Further, these analogues exerted a competitive mode of PL inhibition. Moreover, molecular modelling studies were in agreement with the in vitro results (Pearson's r?=.8682, p?.05). The fluorescence spectroscopic analysis further supported the strong binding affinity of these analogues with PL. A molecular dynamics study (20?ns) indicated that these analogues were stable in a dynamic environment. Thus, the present study highlighted the potential role of indole-thiazolidinedione hybrid analogues as potential PL inhibitors and further optimization might result in the development of new PL inhibitory lead candidates.

Novel N-phenyl-substituted thiazolidinediones protect neural cells against glutamate- and tBid-induced toxicity

Mitochondrial demise is a key feature of progressive neuronal death contributing to acute and chronic neurological disorders. Recent studies identified a pivotal role for the BH3-only protein B-cell lymphoma-2 interacting domain death antagonist (Bid) for such mitochondrial damage and delayed neuronal death after oxygen-glucose deprivation, glutamate-induced excitotoxicity, or oxidative stress in vitro and after cerebral ischemia in vivo. Therefore, we developed new N-phenyl-substituted thiazolidine-2,4-dione derivatives as potent inhibitors of Bid-dependent neurotoxicity. The new compounds 6, 7, and 16 were identified as highly protective by extensive screening in a model of glutamate toxicity in immortalized mouse hippocampal neurons (HT-22 cells). These compounds significantly prevent truncated Bid-induced toxicity in the neuronal cell line, providing strong evidence that inhibition of Bid was the underlying mechanism of the observed protective effects. Furthermore, Bid-dependent hallmarks of mitochondrial dysfunction, such as loss of mitochondrial membrane potential, ATP depletion, as well as impairments in mitochondrial respiration, are significantly prevented by compounds 6, 7, and 16. Therefore, the present study identifies a class of N-phenyl thiazolidinediones as novel Bid-inhibiting neuroprotective agents that provide promising therapeutic perspectives for neurodegenerative diseases, in which Bid-mediated mitochondrial damage and associated intrinsic death pathways contribute to the underlying progressive loss of neurons. Copyright

Synthesis and anticonvulsant activity of 4-oxo and 4-thioxo-8- bromobenzopyran derivatives

Several thiosemicarbazones (7 and 8), 1,3-thiazolidin-4-ones (9, 10, 13, 14) and 2-thioxo-1,3-imidazolidin-4-ones (11) have been prepared starting from 8-bromo-7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-1-benzopyran-6-carbaldehyde (3) and its 4-thio analogue (4). The anticonvulsant activity of all of the synthesized compounds was evaluated against maximal electrical shock (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizures. The neurotoxicity was assessed using the rota-rod test. Some of the tested compounds displayed potent anticonvulsant activity in the scPTZ test. ECV Editio Cantor Verlag.

Ionic liquid-accelerated N-arylation of 5-arylidene-2,4-thiazolidinediones with diaryliodonium salts

An efficient method for the synthesis of N-aryl-5-arylidene-2,4- thiazolidinediones has been developed involving the N-arylation of 5-arylidene-2,4-thiazolidinediones derivatives with diaryliodonium salts in the ionic liquid [bmim]PF6 (1-butyl-

Synthesis and transformations of (imidazolylimino)thiazolidinones

The reaction of ethyl 5-phenylthioureido-3H-imidazole-4-carboxylate with bromoacetic acid afforded (imidazolylimino)thiazolidinones, which were transformed into the corresponding 5-arylidene-4-thiazolidinones by the reactions with aldehydes. Under the conditions of the Knoevenagel reaction, the thiazolidine ring in derivatives of 4-(4-oxothiazolidin-2-ylidene-amino)-3H- imidazole-4-carboxamides was opened to form substituted guanidines.

Reaction of O-alkyl-N-substituted iminothiocarbonates with bromoacetyl bromide. A general method for the synthesis of 3-substituted 1,3-thiazolidine-2,4-diones

Reaction of sodium salts of O-methyl-N-substituted iminothiocaibonates with bromoacetyl bromide represents a new general method for preparation of 3-substituted 1,3-thiazolidine-2,4-diones in good yields and high purity. The structure of the synthesized products has been confirmed by 1H NMR, 13C NMR, IR and mass spectroscopy as well as by independent synthesis.

Synthesis and anticonvulsant activity of new acylthiosemicarbazides and thiazolidines

A number of 1-(3-phenyl-4(3H)-quinazolinone-2-ylmercaptoacetyl)-4-substituted thiosemicarbazide and 2-(3-phenyl-4(3H)-quinazolinone-2-ylmercaptoacetylhydrazono)-3-substit uted 4-thiazolidone derivatives were synthesized and evaluated for anticonvulsant ac

Oxidation of thiourethanes, XII: Oxidative desulfuration of cyclic dithiocarbamates and -carbazates using hydrogen peroxide or hydrogen peroxide/sodium tungstate in a two-phase-system

Cyclic dithiocarbamates and dithiocarbazates were desulfurized to the corresponding 2-oxo-analogues using H2O2 with or without addition of Na2WO4 in a two-phase-system.

Adduct-aldehyde and its use for the preparation of vitamin-D compounds

The invention relates to an adduct-aldehyde of the general formula STR1 wherein R is a hydrogen atom or an optionally etherified or esterified hydroxy group, R1 is an optionally etherified or esterified hydroxy group, and Z is a sulphonyl group or a group of the general formula STR2 wherein A and B are equal or different and represent C1 -C4 alkoxy groups, or wherein A and B together constitute a phenylimino group or a o-phenylene group. The invention also relates to a method of preparing said adduct-aldehyde and to the use of said aldehyde as an intermediate for the preparation of vitamin-D compounds.