23522-37-4

Usage

InChI:InChI=1/C10H9NOS2/c1-7-4-2-3-5-8(7)11-9(12)6-14-10(11)13/h2-5H,6H2,1H3

Upstream product

• 68-11-1 mercaptoacetic acid 
• 614-69-7 2-tolyl isothiocyanate 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 79-07-2 Chloroacetamide 
• 95-53-4 o-toluidine 
• 75-15-0 carbon disulfide 
• 3926-62-3 sodium monochloroacetic acid 
• 623-51-8 ethyl 2-sulfanylacetate 
• 45892-06-6 N-(o-tolyl)dithiocarbamic acid 
• 79-11-8 chloroacetic acid 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 

Downstream Products

• 94330-89-9 5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxo-3-o-tolyl-thiazolidin-4-one 
• 113380-96-4 5-[4-(3-methyl-3H-benzothiazol-2-ylidene)-but-2-enylidene]-2-thioxo-3-o-tolyl-thiazolidin-4-one 
• 113926-27-5 5-[6-(3-methyl-3H-benzothiazol-2-ylidene)-hexa-2,4-dienylidene]-2-thioxo-3-o-tolyl-thiazolidin-4-one 
• 15058-99-8 2-thioxo-3-o-tolyl-thiazolidine-4,5-dione 5-phenylhydrazone 
• 130189-27-4 5-Morpholinomethyl-N-o-tolylrhodanin 
• 75003-47-3 5-Quinolin-2-yl-2-thioxo-3-o-tolyl-thiazolidin-4-one 
• 221286-75-5 5-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-2-thioxo-3-o-tolyl-thiazolidin-4-one 
• 221286-77-7 5-(4-methoxybenzylidene)-3-(2-methylphenyl)-2-thioxothiazolidin-4-one 
• 126751-00-6 5-Oxo-7-phenyl-2-thioxo-3-o-tolyl-2,3,4,5-tetrahydro-thiazolo[4,5-b]pyridine-6-carbonitrile 
• 126751-05-1 2-Thioxo-3-o-tolyl-2,3-dihydro-furo[2,3-d]thiazol-6-one 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors

Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good LYP inhibitory activities (IC50 = 2.85–6.95 μM). Especially, the most potent inhibitor 9r was identified as competitive inhibitor (Ki = 1.09 μM) and bind LYP reversibly. Meanwhile, 9r exhibited better selectivity over other phosphatases than known LYP inhibitor A15. Furthermore, compound 9r could regulate TCR associated signaling pathway in Jurkat T cell.

Identification of para-Substituted Benzoic Acid Derivatives as Potent Inhibitors of the Protein Phosphatase Slingshot

Slingshot proteins form a small group of dual-specific phosphatases that modulate cytoskeleton dynamics through dephosphorylation of cofilin and Lim kinases (LIMK). Small chemical compounds with Slingshot-inhibiting activities have therapeutic potential against cancers or infectious diseases. However, only a few Slingshot inhibitors have been investigated and reported, and their cellular activities have not been examined. In this study, we identified two rhodanine-scaffold-based para-substituted benzoic acid derivatives as competitive Slingshot inhibitors. The top compound, (Z)-4-((4-((4-oxo-2-thioxo-3-(o-tolyl)thiazolidin-5-ylidene)methyl)phenoxy)methyl)benzoic acid (D3) had an inhibition constant (Ki) of around 4 μm and displayed selectivity over a panel of other phosphatases. Moreover, compound D3 inhibited cell migration and cofilin dephosphorylation after nerve growth factor (NGF) or angiotensin II stimulation. Therefore, our newly identified Slingshot inhibitors provide a starting point for developing Slingshot-targeted therapies.

Chiral N-(o-aryl)-thiazolidinediones: Synthesis from rhodanines and investigation on rotational enantiomers by NMR spectroscopy

Sterically hindered N-(o-aryl)-rhodanines (a) (N-(o-aryl)-2-thioxo-4-thiazolidinones) have been synthesized and the N-(o-tolyl) and N-(o-chlorophenyl) derivatives have been converted to their dioxo analogs (b) (N-(o-aryl)-2,4-thiazolidine-diones). The chi

Synthesis and NMR studies of chiral 4-oxazolidinones and rhodanines

Sterically hindered N-(o-tolyl) and N-(o-chlorophenyl) substituted 2-thioxo-4-oxazolidinones 1 and-thiazolidinones (rhodanines) 2 forming enantiomers by partial rotation around the C - N bond are synthesized. Their chirality is proven by the presence of diastereotopic protons (or carbon atoms) detected by 1H or 13C NMR (1c, 2c). In the presence of (S)(+)-1-(9-anthryl)-2,2,2-trifluoroethanol as an auxilliary the enantiomers showed 1H shift differences of 0.01 ppm for otherwise isochronous nuclei.

1H and 13C NMR Studies on 3-Aryl-2-thioxo-4-oxazolidinones and 3-Arylrhodanines

3-Aryl-2-thioxo-4-oxazolidinones and 3-arylrhodanines have been studied for magnetic non-equivalence of diastereotopically related proton and 13C nuclei in rotational isomers, and for steric interactions between the aryl and heterocyclic moieties of these compounds.For the majority of rotational isomers the barriers to internal rotation about the aryl C-N bond were >100 kJ mol-1, due to the steric bulk of the thiocarbonyl group.Chemical isolation of several of the diastereomers was achieved.The enhanced steric effect and the difference in the electronic effect of the sulphur atom in relation to the oxygen atom appeared to have no influence on the small chemical shift differences of the rotational isomers, detected for some 1H and some 13C nuclei.