17385-68-1

Usage

InChI:InChI=1/C10H10N2OS/c1-7-2-4-8(5-3-7)11-10-12-9(13)6-14-10/h2-5H,6H2,1H3,(H,11,12,13)

Upstream product

• 20765-47-3 (N-p-tolyl-carbamimidoylmercapto)-acetic acid 
• 622-52-6 p-methylphenylthiourea 
• 105-39-5 chloroacetic acid ethyl ester 
• 17356-08-0 thiourea 
• 16634-82-5 N-(p-tolyl)-2-chloroacetamide 
• 79-11-8 chloroacetic acid 
• 333-20-0 potassium thioacyanate 
• 105-36-2 ethyl bromoacetate 
• 6281-61-4 1-benzoyl-3-(4-methylphenyl)thiourea 
• 106-49-0 p-toluidine 
• 87942-18-5 C₁₁H₁₄N₂O₂S 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 912969-57-4 (4-chlorothiazol-2-yl)-p-tolylamine 
• 497835-66-2 5-(3-bromo-4-hydroxy-5-methoxy-benzylidene)-3-methyl-2-p-tolylimino-thiazolidin-4-one 
• 17944-95-5 5-{4-[bis-(2-chloro-ethyl)-amino]-benzylidene}-2-(4-methyl-anilino)-thiazol-4-one 
• 23155-43-3 5-(4-Nitro-phenylazo)-2-(p-tolylimino)-thiazolidinon-(4) 
• 20377-44-0 2-chloroacetylimino-3-p-tolyl-thiazolidin-4-one 
• 919364-98-0 2-(p-tolylimino)-5-(3-phenylpropylidene)thiazolidin-4-one 
• 463317-03-5 2-[4-methylphenylimino]-5-(1H-pyridin-2-ylmethylidene)-1,3-thiazolidin-4-one 
• 1164513-71-6 C₁₅H₁₂N₂O₂S 

Relevant academic research and scientific papers

A Library of Thiazolidin-4-one Derivatives as Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitors: An Attempt To Discover Novel Antidiabetic Agents

Protein tyrosine phosphatase 1B (PTP1B) is an important target for the treatment of diabetes. A series of thiazolidin-4-one derivatives 8–22 was designed, synthesized and investigated as PTP1B inhibitors. The new molecules inhibited PTP1B with IC50 values in the micromolar range. 5-(Furan-2-ylmethylene)-2-(4-nitrophenylimino)thiazolidin-4-one (17) exhibited potency with a competitive type of enzyme inhibition. structure–activity relationship studies revealed various structural facets important for the potency of these analogues. The findings revealed a requirement for a nitro group-including hydrophobic heteroaryl ring for PTP1B inhibition. Molecular docking studies afforded good correlation with experimental results. H-bonding and π–π interactions were responsible for optimal binding and effective stabilization of virtual protein-ligand complexes. Furthermore, in-silico pharmacokinetic properties of test compounds predicted their drug-like characteristics for potential oral use as antidiabetic agents.Additionally, a binding site model demonstrating crucial pharmacophoric characteristics influencing potency and binding affinity of inhibitors has been proposed, which can be employed in the design of future potential PTP1B inhibitors.

Synthesis of novel inhibitors of α-amylase based on the thiazolidine-4-one skeleton containing a pyrazole moiety and their configurational studies

Postprandial hyperglycemia can be controlled by delaying the absorption of glucose resulting from carbohydrate digestion. α-Amylase is the initiator of the hydrolysis of polysaccharides, and therefore developing α-amylase inhibitors can lead to development of new treatments for metabolic disorders like diabetes mellitus. In the present work, we set out to rationally develop α-amylase inhibitors based on the thiazolidine-4-one scaffold. The structures of all these newly synthesized hybrids were confirmed by spectroscopic analysis (IR, 1H-NMR, MS). The appearance of two sets of signals for some protons in 1H NMR revealed the existence of a mixture of 2E,5Z (37.1-42.0%) and 2Z,5Z isomers (58.4-62.8%), which was further supported by DFT studies. All the newly synthesized compounds have potential inhibitory properties as revealed through in vitro α-amylase inhibition activity. Compound 5a at 100 μg mL-1 concentration showed a remarkable inhibition of 90.04%. In vitro α-amylase inhibition was further supported by docking studies of compound 5a against the active site of human pancreatic α-amylase (PDB ID: 2QV4). The docking studies revealed that the bonding interactions found between 5a and human pancreatic α-amylase are similar to those responsible for α-amylase inhibition by acarbose.

Synthesis and exploration of configurational dynamics in equilibrating E/Z 2-aryliminothiazolidin-4-ones using NMR and estimation of thermodynamic parameters

In the present study, 2-aryliminothiazolidin-4-ones (3 and 5) were utilized as dynamic chemical systems, whose different states are modulated in a reversible fashion through specific chemical stimuli. The in-depth NMR investigation revealed that the magnitude of rotational energy barrier (ΔG?) is affected markedly by (1) the solvent polarity; (2) the electronic nature of the ring system present on the exocyclic CQN bond and (3) the temperature of the system. The derivatives of 5-(3-arylallylidene)-2-(arylimino)thiazolidin-4-one exist in two isomeric forms at room temperature in DMSO-d6: (2E,5Z,7E) ? (2Z,5Z,7E). The stereodynamics of the synthesized derivatives (5a-5t) has been investigated using variable temperature dynamic 1H-NMR (VT DNMR). The ΔG? values (≈15 kcal mol?1) estimated for the dynamic process depict a significant barrier between two forms in solution at ambient temperature. To go a step further, line shape analysis was also performed to get a clear understanding of the equilibration mechanism.

A 5 - (1 H - indole - 3 - methylene) - 1, 3 - thiazolidine - 4 - ketone derivative and its synthetic method and application

The invention relates to 5-(1H-indolyl-3-methylene)-1,3-thiazolidinyl-4-one derivatives, and a synthesis method and application thereof. By using ethanol and/or water as a solvent, substituted 2-substituted-imino-1,3-thiazolidinyl-4-one and 1H-indolyl-3-formaldehyde are subjected to reflux reaction under the catalytic condition of piperidine through intermolecular dehydration condensation reaction to form methylene linking group, thereby obtaining the 5-(1H-indolyl-3-methylene)-1,3-thiazolidinyl-4-one derivatives. The intermediate 2-substituted-iminothiazolidinyl-4-one is prepared by carrying out cyclization reaction on various monosubstituted ethyl thiocarbamide chloroacetates or chloroacetic acids in a low-boiling solvent under reflux conditions, and the intermediate 2-substituted-imino-3-substituted-1,3-thiazolidinyl-4-one is prepared by carrying out a green environment-friendly synthesis technique on various disubstituted symmetric thiocarbamides and chloroacetic acids. The bioactivity preliminary screening experiment result of all the target compounds on the enzyme molecular level indicates that the target products have certain inhibition activity on PTP1B and CDC25B to different degrees.

New thiazolidinyl analogs containing pyridine ring: Synthesis, biological evaluation and QSAR studies

A series of pyridine derivatives of thiazolidin-4-ones (4a-4o) has been synthesized. Structures of these compounds were established on the basis of elemental analysis, IR, 1H NMR, 13C NMR, and Mass spectral data. All the synthesized compounds have been evaluated for their anti-inflammatory and analgesic effects. The results showed that compound 2-[4-methylphenylimino]-5-(1H-pyridin-2-ylmethylidene)-1,3-thiazolidin-4-one (4d), 2-(2,4-dinitro-phenylhydrazinylidine)-5-(1H-pyridin-2-yl-methylidene)-1,3- thiazolidin-4-one (4h), and 2-[3-nitro-phenylimino]-5-(1H-pyridin-2-yl- methylidene)-1,3-thiazolidin-4-one (4j) exhibited good anti-inflammatory and analgesic activity. Compound 4h was found to be the most active compound of the series with an interesting dual anti-inflammatory and analgesic activity. Docking simulation was performed to position synthesized compounds into the active site of COX-2. The relationships of energy-based docking score with analgesic and anti-inflammatory activities were also investigated by linear regression method. The QSAR models with R 2 of 0.621 and 0.740 were developed for analgesic and anti-inflammatory activities, respectively.

Use of thiazole derivatives and analogues in disorders caused by free fatty acids

There is provided a use of a compound of formula I, wherein X, T, Y, W, A1, A2, R1, R5 and R6 have meanings given in the description, for the manufacture of a medicament for the treatment of a disorde

NEW COMBINATION FOR USE IN THE TREATMENT OF CANCER

There is provided combination products comprising (a) a compound of formula (I): wherein X, Y, T, W, A1, A2 R1, R5 and R6 have meanings given in the description, and (b) tamoxifen or an aromatase inhi

Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells

Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.

[4-(Imidazol-1-yl)thiazol-2-yl]phenylamines. A novel class of highly potent colchicine site binding tubulin inhibitors: Synthesis and cytotoxic activity on selected human cancer cell lines

Synthesis and cytotoxic activity in the submicromolar range of a series of [4-(imidazol-1-yl)thiazol-2-yl]-phenylamines are described. Cell cycle dependent cytotoxicity on RKO human colon carcinoma cells with inducible expression of p27kip1 and the influence on microtubule formation were investigated. Considering the significant correlation between the IC50 values of tubulin polymerization inhibition, [3H]colchicine competition, and cytotoxicity of the investigated compounds, tubulin is the main cellular target. The inhibition of microtubule formation was shown to be mediated by interference with the colchicine binding site of tubulin. In depth analysis of the investigated compounds allowed the identification of modifications that altered the pharmacological profile of the compounds from a mitosis-inducing phenotype to a G1 cell cycle arresting phenotype.

Reaction of Methyl (Phenylhydrazonomethylthio)acetate with Sodium Methoxide

The reaction of methyl (phenylhydrazonomethylthio)acetate 1 with sodium methoxide in methanol at 30 deg C was found to give initially 5-oxo-4-phenyl-5,6-dihydro-1,3,4-thiadizine 2, which then rearranged to 2-(phenylimino)-4-oxothiazolidine 3 in quantitative yield via cleavage of the nitrogen-nitrogen bond.Keywords-methyl(phenylhydrazonomethylthio)acetate; 5-oxo-4-phenyl-5,6-dihydro-1,3,4-thiadiazine; 2-(phenylimino)-4-oxothiazolidine; ring contraction; nitrogen-nitrogen bond cleavage