177703-41-2

Basic information

• Product Name: 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione
• Synonyms: 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione
• CAS NO: 177703-41-2
• Molecular Weight: 250.235
• Mol File: 177703-41-2.mol

Chemical Properties

• CAS DataBase Reference: 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione(177703-41-2)
• EPA Substance Registry System: 5-(4-nitro-benzylidene)-thiazolidine-2,4-dione(177703-41-2)

Safety Data

• Hazardous Substances Data: 177703-41-2(Hazardous Substances Data)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 555-16-8 4-nitrobenzaldehdye 
• 41468-11-5 sodium hydroxy(4-nitrophenyl)methanesulfonate 

Downstream Products

• 1442655-47-1 N-(4-((Z)-(3-(4-tert-butylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-46-0 N-(4-((Z)-(3-(4-methylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-45-9 N-(4-((Z)-(3-(4-trifluoromethylbenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-44-8 N-(4-((Z)-(3-(3-chlorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-43-7 N-(4-((Z)-(3-(4-chlorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-42-6 N-(4-((Z)-(3-(3-fluorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-41-5 N-(4-((Z)-(3-(4-fluorobenzyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-40-4 N-(4-((Z)-(3-phenylethyl-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-39-1 N-(4-((Z)-(3-benzyl-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-2-bromoacrylamide 
• 1442655-38-0 2-bromo-N-(4-((Z)-(3-ethyl-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)acrylamide 
• 1442655-37-9 2-bromo-N-(4-((Z)-(3-methyl-2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)acrylamide 
• 1442655-27-7 (Z)-3-(4-tert-butylbenzyl)-5-(4-aminobenzylidene)thiazolidine-2,4-dione 
• 1442655-26-6 (Z)-5-(4-aminobenzylidene)-3-methylthiazolidine-2,4-dione 
• 1442655-25-5 (Z)-3-(4-(trifluoromethyl)benzyl)-5-(4-aminobenzylidene)thiazolidine-2,4-dione 

Relevant articles and documents

Acetic anhydride-promoted one-pot condensation of 2,4-thiazolidinedione with bisulfite adducts of aldehydes

We describe a simple and efficient one-pot method for condensing bisulfite adducts of aromatic aldehydes directly with 2,4-thiazolidinedione catalyzed by acetic anhydride. The two main highlights of this study are the one-pot condensation of bisulfite adducts with 2,4-thiazolidinedione in non-aqueous media and the use of Design of Experiment to understand and optimize the reaction conditions. This methodology was then generalized using other active methylene compounds, such as malononitrile.

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

Green synthesis, biological activity evaluation, and molecular docking studies of aryl alkylidene 2, 4-thiazolidinedione and rhodanine derivatives as antimicrobial agents

Aims and Objective: The magic scaffolds rhodanine and thiazolidine are very important heterocyclic compounds in drug design and discovery. Those are important heterocyclic compounds that have attracted a great deal of attention due to the fact that they e

Reaction pathway of POCl3-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione

We investigated the POCl3-mediated transformation of aromatic bisulfite adducts to the corresponding 5- arylidenethiazolidine-2,4-diones. The in situ transformation of an aromatic bisulfite adduct to the parent aldehyde in a non-aqueous non-pol

Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalyzed by lipoprotein lipase

A screening of using different lipases to catalyze the Knoevenagel reaction was realized, and lipase lipoprotein (LPL) from Aspergillus niger showed the best catalytic performance. The reaction conditions including solvent, enzyme loading, and temperature were screened to improve the reaction efficiency. Various kinds of substrates were investigated, and almost all the target products were obtained in good to excellent yields (76-98%) with Z configuration exclusively. This procedure provides a novel, green and efficient method for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds.

Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts

The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4- thiazolidinedione's has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione's with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene) thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.

Evaluation of michael-type acceptor reactivity of 5-benzylidenebarbiturates, 5-benzylidenerhodanines, and related heterocycles using NMR

Despite existing experimental and computational tools to assess the risk, the non-specific chemical modification of protein thiol groups remains a significant source of false-positive hits, particularly in academic drug discovery. Herein, we describe the

Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds

Δ2-Troglitazone derivatives were shown to exhibit anti-proliferative activity in a PPARγ-independent manner. We prepared various compounds in order to increase their potency and decrease their toxicity towards non-malignant primary cultured hepatocytes. Many compounds induced viabilities less than 20% at 10 μM on various cancer cell lines. Furthermore, five of them showed hepatocyte viability of 80% or more at 200 μM. In addition, compounds 17 and 18 exhibited promising maximum tolerated doses on a murine model, enabling future investigations.

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.

Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry

Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.