3774-99-0

Basic information

• Product Name: (5E)-5-benzylidene-1,3-thiazolidine-2,4-dione
• Synonyms: 5-benzylidene-1,3-thiazolane-2,4-dione
• CAS NO: 3774-99-0
• Molecular Formula: C₁₀H₇NO₂S
• Molecular Weight: 205.2331
• Mol File: 3774-99-0.mol
• Article Data: 87

Chemical Properties

• Density: 1.415g/cm³
• Refractive Index: 1.703
• CAS DataBase Reference: (5E)-5-benzylidene-1,3-thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-5-benzylidene-1,3-thiazolidine-2,4-dione(3774-99-0)
• EPA Substance Registry System: (5E)-5-benzylidene-1,3-thiazolidine-2,4-dione(3774-99-0)

Safety Data

• Hazardous Substances Data: 3774-99-0(Hazardous Substances Data)

Usage

General Description

(5E)-5-benzylidene-1,3-thiazolidine-2,4-dione, also known as TZD, is a chemical compound with a thiazolidinedione ring structure. It is commonly used as a building block for the synthesis of various pharmaceuticals, including antidiabetic drugs such as pioglitazone and rosiglitazone. TZD derivatives have shown to have potential therapeutic effects in the treatment of diabetes, inflammation, and cancer. Additionally, research has suggested that TZD compounds may also possess antioxidant and neuroprotective properties. The chemical structure of (5E)-5-benzylidene-1,3-thiazolidine-2,4-dione makes it a versatile and valuable compound in medicinal chemistry and drug discovery.

Upstream product

• 38771-64-1 2-anilino-5-benzylidene-thiazol-4-one 
• 590-28-3 potassium cyanate 
• 68-11-1 mercaptoacetic acid 
• 1627-70-9 benzaldehyde (5-benzylidene-4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 463-58-1 carbon oxide sulfide 
• 7223-30-5 3-phenyl-propynoic acid amide 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 2295-31-0 thiazoline-2,4-dione 
• 716336-73-1 1-benzylideneurea 
• 2362-79-0 N-(4-chlorobenzylidene)aniline 
• 4657-12-9 sodium hydroxy(phenyl)methanesulfonate 
• 100-52-7 benzaldehyde 
• 74037-15-3 5-benzylidene-thiazolidine-2,4-dione 2-oxime 

Downstream Products

• 35490-97-2 5-benzylidene-3-(2-pyridin-2-yl-ethyl)-thiazolidine-2,4-dione 
• 35490-98-3 5-benzylidene-3-(2-pyridin-4-yl-ethyl)-thiazolidine-2,4-dione 
• 67309-78-8 5-benzylidene-2-ethoxy-thiazol-4-one 
• 37868-77-2 3-ethyl-1,3-thiazolidine-2,4-dione 
• 55547-89-2 (E,Z)-5-Benzylidene-3-ethyl-2,4-dioxo-1,3-thiazolidine 
• 53087-98-2 5-benzhydryl-thiazolidine-2,4-dione 
• 39683-47-1 3-anilinomethyl-5-benzylidene-thiazolidine-2,4-dione 
• 55547-90-5 [(3-ethyl-2,4-dioxo-thiazolidin-5-yl)-phenyl-methyl]-phosphonic acid diethyl ester 
• 14016-49-0 5-benzylidene-4-thioxothiazolidin-2-one 
• 92876-58-9 Oxim d. 2-Oxo-3-phenyl-propionhydroxamsaeure 
• 3775-03-9 5-benzylidene-oxazolidine-2,4-dione 
• 39726-52-8 3-hydroxymethyl-5-benzylidene-2,4-thiazolidinedione 
• 74942-56-6 6-benzyl-2-phenyl-3-phenylazo-1,2,4-triazin-5(2H)-one 
• 74942-55-5 6-benzyl-2-phenyl-3-phenylhydrazino-1,2,4-triazin-5(2H)-one 

Relevant articles and documents

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A synthesis of phosphorylated 2,4-dioxothiazolidine derivatives

The zwitterionic 1:1 intermediates generated from trialkyl phosphites and dialkyl acetylenedicarboxylates are trapped by 2,4-thiazolidinedione and 5-arylidene-2,4-thiazolidinediones to produce dialkyl 2-(2,4-dioxothiazolidin-3- yl)-3-(dialkoxyphosphoryl)

Synthesis, anticancer, and antibacterial studies of benzylidene bearing 5-substituted and 3,5-disubstituted-2,4-thiazolidinedione derivatives

Aim: To develop novel compounds having potent anticancer and antibacterial activities. Background: Several studies have proved that benzylidene analogues of clinical 2,4-TZDs, such as troglitazone and ciglitazone, have more potent antiproliferative activity than their parent com-pounds. Literature studies also revealed that the attachment of more heterocyclic rings, containing nitrogen on 5th position of 2,4-TZD, can enhance the antimicrobial activity. Hence, attachment of various moieties on the benzylidene ring may produce safe and effective compounds in the future. Objective: The objective of the present study was to synthesize a set of novel benzylidene ring containing 5-and 3-substituted-2,4-thiazolidinedione derivatives and evaluate them for their anti-cancer and antibacterial activity. Method: The synthesized compounds were characterized by IR, NMR, mass, and elemental stud-ies. The in vitro cytotoxicity studies were performed for human breast cancer (MCF-7) and human lung cancer (A549) cells and HepG2 cell-line and compared to standard drug doxorubicin by MTT assay. Antimicrobial activity of the synthesized 2,4-thiazolidinediones derivatives was carried out using the cup plate method with slight modification. Result: The results obtained showed that TZ-5 and TZ-13 exhibited good antiproliferative activity against A549 cancer cell-line, whereas TZ-10 exhibited moderate antiproliferative activity against HepG2 cell-line when compared to standard drug doxorubicin. TZ-5 also exhibited reasonable activity against the MCF-7 cell-line with doxorubicin as standard. TZ-4, TZ-5, TZ-6, TZ-7, and TZ-16 exhibited remarkable antibacterial activity against Gram positive and moderate activity against Gram negative bacteria with the standard drug ciprofloxacin. Conclusion: Attachment of heterocyclic rings containing nitrogen as the hetero atom improves the anticancer and antimicrobial potential. Attachment of electronegative elements like halogens can also enhance the antimicrobial activity. Further structure modifications may lead to the development of more potent 2,4-TZD leads that can be evaluated for further advanced studies.

Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives

In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a