98949-12-3

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 89-98-5 2-chloro-benzaldehyde 
• 6318-36-1 (E,Z)-5-(2-chlorophenylmethylene)-4-oxo-2-thioxothiazolidine 
• 76979-32-3 5-[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-2-methylsulfanyl-thiazol-4-one 

Downstream Products

• 1307299-68-8 (Z)-5-(2-chlorobenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Antileishmanial activity evaluation of thiazolidine-2,4-dione against Leishmania infantum and Leishmania braziliensis

Leishmaniasis is responsible for approximately 65,000 annual deaths. Despite the mortality data, drugs available for the treatment of patients are insufficient and have moderate therapeutic efficacy in addition to serious adverse effects, which makes the development of new drugs urgent. To achieve this goal, the integration of kinetic and DSF assays against parasitic validated targets, along with phenotypic assays, can help the identification and optimization of bioactive compounds. Pteridine reductase 1 (PTR1), a validated target in Leishmania sp., is responsible for the reduction of folate and biopterin to tetrahydrofolate and tetrahydrobiopterin, respectively, both of which are essential for cell growth. In addition to the in vitro evaluation of 16 thiazolidine-2,4-dione derivatives against Leishmania major PTR1 (LmPTR1), using the differential scanning fluorimetry (ThermoFluor), phenotypic assays were employed to evaluate the compound effect over Leishmania braziliensis (MHOM/BR/75/M2903) and Leishmania infantum (MHOM/BR/74/PP75) promastigotes viability. The ThermoFluor results show that thiazolidine-2,4-dione derivatives have micromolar affinity to the target and equivalent activity on Leishmania cells. 2b is the most potent compound against L. infantum (EC50 = 23.45 ± 4.54 μM), whereas 2a is the most potent against L. braziliensis (EC50 = 44.16 ± 5.77 μM). This result suggests that lipophilic substituents on either—meta and/or—para positions of the benzylidene ring increase the potency against L. infantum. On the other hand, compound 2c (CE50 = 49.22 ± 7.71 μM) presented the highest selectivity index.

Ultrasound-assisted one-pot green synthesis of new N- substituted-5-arylidene-thiazolidine-2,4-dione-isoxazoline derivatives using NaCl/Oxone/Na3PO4 in aqueous media

A rapid and green method for the synthesis of novel N-thiazolidine-2,4-dione isoxazoline derivatives 5 from N-allyl-5-arylidenethiazolidine-2,4-diones 3 as dipolarophiles with arylnitrile oxides via 1,3-dipolar cycloaddition reaction. The corresponding N-allyl substituted dipolarophiles were prepared by one-pot method from thiazolidine-2,4-dione with aldehydes using Knoevenagel condensation followed by N-allylation of thiazolidine-2,4-dione in NaOH aqueous solution under sonication. In addition, the isoxazoline derivatives 5 were synthesized by regioselective and chemoselective 1,3-dipolar cycloaddition using inexpensive and mild NaCl/Oxone/Na3PO4 as a Cl source, oxidant and/or catalyst under ultrasonic irradiation in EtOH/H2O (v/v, 2:1) as green solvent. All synthesized products are furnished in good yields in the short reaction time, and then their structures were confirmed by NMR, mass spectrometry and X-ray crystallography analysis.

Exploration of some thiazolidine-2,4-dione and 2-oxoindoline derivatives incorporating 3,4,5-trimethoxybenzyl moiety as novel anticancer agents

Background: Combrestastatin A-4 (CA-4) is a potent anticneoplastic and antiangiogenesis natural substance isolated from Combretum caffrum. Over the past two decades, numerous derivatives of CA-4 have been discovered. However, none of these derivatives has reached the clinical stage. Thus, continuing effort is needed in developing CA-4 analogues with improved pharmacological properties. Methods: In this study, two series of thiazolidine-2,4-dione and 2-oxoindoline derivatives incorporating 3,4,5-trimethoxybenzyl scaffold were designed and synthesized as CA-4 analogues. Results: Numerous CA-4 analogues bearing thiazolidine-2,4-dione/2-oxoindoline have been synthesized. These compounds were evaluated against several human cancer cell lines. It was found that a series of 5/7-substituted-1-(3,4,5-trimethoxy)benzylindoline-2,3-diones (2a-g) exhibited significant cytotoxicity. Especially compound 2d bearing a 5-bromo substituent showed the best activity with IC50 values in sub-microgram/mL scale in four human cancer cell lines tested. This compound also exhibited potent tubulin polymerization inhibitory activity. A series of (Z)-5-arylidene-3-(3,4,5-trimethoxybenzyl)thiazolidine-2,4-diones (6a-j), on the other hand, displayed only moderate cytotoxic activities with only compound 6a showing comparable cytotoxicity to 2d. Finally, in silico molecular modeling and drug-likeness profiling revealed that five compounds 2b, 2d, 2e, 3e and 6a bound to tubulin active binding sites with strong binding affinities. Conclusion: This study discovered some novel CA-4 analogues with cytotoxic potency and antitubulin activity acceptable to be further developed as effective anticancer drug candidates.

Copper(II)-complex functionalized magnetite nanoparticles: a highly efficient heterogeneous nanocatalyst for the synthesis of 5-arylidenthiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-one

Abstract: Magnetite nanoparticles (MNPs) have proved to be a useful support for heterogeneous catalysis. We have synthesized Fe3O4 MNPs functionalized with a copper(II) complex, and tested the resulting material as a heterogeneous nanocatalyst. The catalyst was tested for aldol condensation reactions between aliphatic/aromatic aldehydes and rhodanine or thiazolidine-2,4-dione (TZD) derivatives under reflux in ethanol, giving the target products in high yield. Environmentally benign chemistry, short reaction times, simple work-up, excellent yields, and the reusability of the new nanocatalyst are beneficial features of the present study. The nanocatalyst was characterized by scanning electron microscopy, vibrating sample magnetometery, thermogravimetry, X-ray diffraction, and energy-dispersive X-ray analyses. The data showed that the magnetic nanoparticles are super-paramagnetic with a size range of 10–20?nm. Graphical Abstract: [Figure not available: see fulltext.].

Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound

The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.

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.

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.

Synthesis of 5-arylidene-2,4-thiazolidinediones by Knoevenagel condensation catalyzed by baker's yeast

An ecofriendly baker's yeast catalyzed Knoevenagel condensation of aromatic aldehydes and active methylene compounds has been performed. The developed protocol has been found to be applicable for obtaining 5-arylidene-2,4- thiazolidinediones, the precursors of hypoglycemic agents. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011.

Design, synthesis and characterization of some novel 3-coumarinyl- 5-aryliden-1,3-thiazolidine-2,4-diones and their antioxidant activity

In our effort to obtain biologically active compounds, new 3,5-disubstituted 1,3-thiazolidine-2,4- diones (5a - r) were synthesized. A series of 5-arylmethylidene-1,3-thiazolidine-2,4-diones (3a - r) were prepared by Knoevenagel reaction from 1,3-thiazolidine-2,4-dione (2) and appropriate aromatic aldehydes. Condensation of 3a - r with 7-hydroxy-4-bromomethyl-2-oxo- 2H-chromene (1) afforded novel 3-(7-hydroxy-2-oxo-2H-chromen-4-ylmethyl)-5- arylidene-1,3-thiazolidine-2,4-diones 5a - r. Compounds 3a - r and 5a - r were evaluated for their antioxidant activity (DPPH free radical scavenging activity).

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