1055980-73-8

Basic information

• Product Name: (5Z)-5-(3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione
• Synonyms: (5Z)-5-(3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione
• CAS NO: 1055980-73-8
• Molecular Weight: 250.235
• Mol File: 1055980-73-8.mol

Chemical Properties

• CAS DataBase Reference: (5Z)-5-(3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z)-5-(3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione(1055980-73-8)
• EPA Substance Registry System: (5Z)-5-(3-nitrobenzylidene)-1,3-thiazolidine-2,4-dione(1055980-73-8)

Safety Data

• Hazardous Substances Data: 1055980-73-8(Hazardous Substances Data)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 99-61-6 3-nitro-benzaldehyde 
• 461-72-3 2,4-imidazolidinedione 

Downstream Products

• 1442655-56-2 N-(3-((Z)-(3-(4-tert-butylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-55-1 N-(3-((Z)-(3-(4-methylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-54-0 N-(3-((Z)-(3-(4-trifluoromethylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-53-9 N-(3-((Z)-(3-(3-chlorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-52-8 N-(3-((Z)-(3-(4-chlorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-51-7 N-(3-((Z)-(3-(3-fluorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-50-6 N-(3-((Z)-(3-(4-fluorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-49-3 N-(3-((Z)-(3-phenylethyl-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-48-2 N-(3-((Z)-(3-benzyl-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-36-8 (Z)-3-(4-tert-butylbenzyl)-5-(3-aminobenzylidene)thiazolidine-2,4-dione 
• 1442655-35-7 (Z)-3-(4-methylbenzyl)-5-(3-aminobenzylidene)thiazolidine-2,4-dione 
• 1442655-34-6 (Z)-3-(4-(trifluoromethyl)benzyl)-5-(3-aminobenzylidene)thiazolidine-2,4-dione 
• 1442655-33-5 (Z)-3-(3-chlorobenzyl)-5-(3-aminobenzylidene)thiazolidine-2,4-dione 
• 1442655-32-4 (Z)-3-(4-chlorobenzyl)-5-(3-aminobenzylidene)thiazolidine-2,4-dione 

Relevant articles and documents

A convenient synthesis of 5-arylidenethiazolidine-2,4-diones catalyzed by alkaline ionic liquid

A series of 5-arylidenethiazolidine-2,4-diones was synthesized by the Knoevenagel condensation of thiazolidine-2,4-dione with aromatic aldehydes with alkaline ionic liquid l-butyl-3-mefhylimidazolium hydroxide ([bmim]OH) as dual solvent and catalyst. This

Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies

Benzoxazolyl linked meta- and para-substituted new chemical entities (5a–5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by 1H NMR, 13C NMR, FT-IR, and HRMS spectra

Anticancer activity of novel hybrid molecules containing 5-benzylidene thiazolidine-2,4-dione

Hybridization of two different bioactive molecules with different mechanism of action is one of the methods that are being adopted to treat cancer. Molecules bearing a thiazolidine-2,4-dione scaffold have been recognized as antineoplastic agents with a broad spectrum of activity against many cancer cell lines. In this manuscript we have described the synthesis and biological evaluation of two series of N-3-substituted-5-arylidene thiazolidine-2,4-diones, bearing the α-bromoacryloylamido moiety at the para- or meta-position on the phenyl of the arylidene portion. We have observed that selected compounds 5a, 5c and 5g suppress proliferation of human myeloid leukaemia HL-60 and U937 cells by triggering morphological changes and internucleosomal DNA fragmentation, which are well-known features of apoptosis. Finally, our results indicated that the investigated compounds induced apoptotic cell death through a mechanism that involved activation of multiple caspases and was also associated with the release of cytochrome c from the mitochondria.

Discovery of novel 5-benzylidenerhodanine and 5-benzylidenethiazolidine-2, 4-dione inhibitors of MurD ligase

We have designed, synthesized, and evaluated 5-benzylidenerhodanine-and 5-benzylidenethiazolidine-2,4-dione-based compounds as inhibitors of bacterial enzyme MurD with E. coli IC50 in the range 45-206 μM. The high-resolution crystal structure o

Synthesis and biological evaluation of new glutamic acid-based inhibitors of MurD ligase

Mur ligases catalyze the biosynthesis of the UDP-MurNAc-pentapeptide precursor of peptidoglycan, an essential polymer of bacterial cell-wall. They constitute attractive targets for the development of novel antibacterial agents. Here we report on the synth

Structure-activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors

The structure-activity relationships (SARs) of 5-arylidene-2,4- thiazolidinediones active as aldose reductase inhibitors (ARIs) were extended by varying the substitution pattern on the 5-arylidene moiety and on N-3. In particular, the introduction of an a

A convenient synthesis of 5-benzylidenethiazolidine-2, 4-diones under microwave irradiation without solvent

A series of 5-benzylidenethiazolidine-2,4-diones was synthesised by the Knoevenagel condensation of aromatic aldehydes with thiazolidine-2,4-dione in the presence of catalytic amounts of piperidine and acetic acid under microwave irradiation without solvent in good yields.