4695-17-4

Basic information

• Product Name: 2,4-Thiazolidinedione, 5-phenyl-
• CAS NO: 4695-17-4
• Molecular Formula: C9H7NO2S
• Molecular Weight: 193.226
• Mol File: 4695-17-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,4-Thiazolidinedione, 5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Thiazolidinedione, 5-phenyl-(4695-17-4)
• EPA Substance Registry System: 2,4-Thiazolidinedione, 5-phenyl-(4695-17-4)

Safety Data

• Hazardous Substances Data: 4695-17-4(Hazardous Substances Data)

Usage

Chemical class

Thiazolidinedione derivatives

Common use

Pharmaceutical intermediate in synthesizing drugs, especially for diabetes treatment

Properties

Anti-inflammatory: Studied for potential anti-inflammatory properties
Anti-diabetic: Studied for potential anti-diabetic properties
Metabolism modulation: Ability to modulate glucose and lipid metabolism

Therapeutic potential

Potential treatment for various inflammatory and metabolic disorders

Interest

Researchers and pharmaceutical companies are interested in its therapeutic applications

Upstream product

• 490-55-1 amiphenazole 
• 36387-87-8 5-phenyl-2-(phenylamino)thiazol-4(5H)-one 
• 1762-68-1 (RS)-2-imino-5-phenylthiazolidine-4-one 
• 7647-01-0 hydrogenchloride 
• 115164-38-0 α-thiocyanato-phenylacetic acid ethyl ester 
• 33512-02-6 3-phenyl-2,2-oxiranedicarbonitrile 
• 98-80-6 phenylboronic acid 
• 17356-08-0 thiourea 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 5798-79-8 bromo-phenyl-acetonitrile 
• 103-80-0 phenylacetyl chloride 
• 79036-01-4 C₁₃H₁₅N₃O₂S 
• 19078-72-9 bromo(phenyl)acetyl chloride 

Downstream Products

• 86106-60-7 N-methyl-4-hydroxy-5-phenyl-5(3,4,5-trimethoxybenzyl)thiazolidin-2-one 
• 86106-29-8 3-Methyl-5-phenyl-5-(3,4,5-trimethoxy-benzyl)-thiazolidine-2,4-dione 
• 86106-37-8 5-ethyl-4-formyloxy-7-methyl-7-phenyl-1-aza-8-thiabicyclo<4.3.0>-nonan-9-one 
• 86106-61-8 N-methyl-5-benzyl-4-hydroxy-5-phenylthiazolidin-2-one 
• 86106-30-1 5-Benzyl-3-methyl-5-phenyl-thiazolidine-2,4-dione 
• 86106-38-9 N-(Z-hex-3-enyl)-4-hydroxy-5-methyl-5-phenylthiazolidin-2-one 
• 86106-28-7 3-((Z)-Hex-3-enyl)-5-methyl-5-phenyl-thiazolidine-2,4-dione 
• 84666-14-8 5,6,7-trimethoxy-3-methyl-2-oxo-10-phenylindano<2,1-d>thiazolidine 
• 4695-02-7 3-methyl-5-phenylthiazolidine-2,4-dione 
• 86106-27-6 3-((Z)-Hex-3-enyl)-5-phenyl-thiazolidine-2,4-dione 

Relevant articles and documents

Identification of a New Zinc Binding Chemotype by Fragment Screening

The discovery of a new zinc binding chemotype from screening a nonbiased fragment library is reported. Using the orthogonal fragment screening methods of native state mass spectrometry and surface plasmon resonance a 3-unsubstituted 2,4-oxazolidinedione fragment was found to have low micromolar binding affinity to the zinc metalloenzyme carbonic anhydrase II (CA II). This affinity approached that of fragment sized primary benzenesulfonamides, the classical zinc binding group found in most CA II inhibitors. Protein X-ray crystallography established that 3-unsubstituted 2,4-oxazolidinediones bound to CA II via an interaction of the acidic ring nitrogen with the CA II active site zinc, as well as two hydrogen bonds between the oxazolidinedione ring oxygen and the CA II protein backbone. Furthermore, 3-unsubstituted 2,4-oxazolidinediones appear to be a viable starting point for the development of an alternative class of CA inhibitor, wherein the medicinal chemistry pedigree of primary sulfonamides has dominated for several decades.

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The nucleophilic ring opening of gem dicyano epoxides by N-substituted or N-N′ disubstituted thioureas leads to 2-imino 4-thiazolidinones, via postulated cyanoformyl intermediates, compounds 7 can exist in tautomeric equilibrium with a tautomeric 2-amino 4-hydroxy thiazolines. However, the cyanoformyl intermediates evolve differently when dicyano epoxides are reacted with 2-thioxobenzoxazole, 2-(aryl cyanoformyl) methylene be.

Studies on antidiabetic agents. III. 5-arylthiazolidine-2,4-diones as potent aldose reductase inhibitors

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