39123-65-4

Upstream product

• 622-78-6 Benzyl isothiocyanate 
• 56-40-6 glycine 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 1399859-85-8 N-benzyl-N'-(2'-acetamido)thiourea 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 616-34-2 methoxycarbonylmethylamine 
• 134124-35-9 N-Benzyl-N'-(carboxymethyl)thiourea 

Downstream Products

• 23269-10-5 1-benzyl-1H-imidazole-2-thione 
• 1356003-68-3 (4Z)-1-benzyl-4-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-4,5-dihydro-1H-imidazol-5-one 
• 875424-21-8 (5Z)-3-benzyl-5-(4-methoxybenzylidene)-2-thiohydantoin 
• 287198-16-7 3-benzyl-2-(methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one 
• 91025-37-5 ethyl 3-benzyl-2-sulfanylidene-2,3-dihydro-1H-imidazole-4-carboxylate 
• 1609282-78-1 1-benzyl-2-(methylthio)-5-imidazolcarbonitrile 
• 80304-50-3 1-benzyl-5-hydroxymethylimidazole 
• 82830-36-2 1-Benzyl-5-(chloromethyl)-1H-imidazolium chloride 
• 76075-21-3 ethyl 1-benzyl-1H-imidazole-5-carboxylic acid 
• 110074-55-0 C₅H₅Ti(C₆H₅CH₂C₃H₂N₂OS)3 

Relevant academic research and scientific papers

Novel synthesis of 3-substituted 2-thiohydantoins via aza-Wittig reaction on poly(ethylene glycol)

A novel method for the liquid-phase combinatorial synthesis of 3-substituted-2-thiohydantoin has been developed by using poly (ethylene glycol)-supported isothiocyanate. The PEG-supported isothiocyanate was obtained from the reaction of PEG with bromoacet

HETEROCYCLIC INTEGRIN AGONISTS

The present invention provides polycyclic oxothioxoimidazolidines, dioxoimidazolines, oxothioxooxazolidines, dioxooxazolidines, and related compounds, which are useful as integrin agonists. Methods for the treatment of integrin-mediated diseases such as cancer are also described.

Synthesis, characterization, and cytotoxicity of binuclear copper(II) complexes with tetradentate nitrogen-containing ligands bis-5-(2-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-ones

A treatment of the N4-type organic ligands containing two 5-(2-pyridylmethylidene)-2-thio-3,5-dihydro-4H-imidazol-4-one fragments linked by (CH2)2 bridges between the sulfur atoms with CuCl2 affords to binuclear

Inhibition of Cancer-Associated Mutant Isocitrate Dehydrogenases by 2-Thiohydantoin Compounds

Somatic mutations of isocitrate dehydrogenase 1 (IDH1) at R132 are frequently found in certain cancers such as glioma. With losing the activity of wild-type IDH1, the R132H and R132C mutant proteins can reduce α-ketoglutaric acid (α-KG) to d-2-hydroxyglutaric acid (D2HG). The resulting high concentration of D2HG inhibits many α-KG-dependent dioxygenases, including histone demethylases, to cause broad histone hypermethylation. These aberrant epigenetic changes are responsible for the initiation of these cancers. We report the synthesis, structure-activity relationships, enzyme kinetics, and binding thermodynamics of a novel series of 2-thiohydantoin and related compounds, among which several compounds are potent inhibitors of mutant IDH1 with Ki as low as 420 nM. X-ray crystal structures of IDH1(R132H) in complex with two inhibitors are reported, showing their inhibitor-protein interactions. These compounds can decrease the cellular concentration of D2HG, reduce the levels of histone methylation, and suppress the proliferation of stem-like cancer cells in BT142 glioma with IDH1 R132H mutation.

Preparation of 2'-13c-l-histidine starting from 13c-thiocyanate: Synthetic access to any site-directed stable isotope enriched l-histidine

1-Benzyl-2-(methylthio)-imidazole-5-ketone is obtained in a few simple steps starting from thiocyanate and glycine amide (glycin). Subsequent treatment with diethyl phosphorocyanidate and functional group manipulations gives 1-benzyl-5-chloromethylimidazolium chloride. This compound is converted under mild O'Donnell conditions into the corresponding L-histidine derivative. After deprotection L-histidine is obtained in good yield and 99% enantiomeric excess. 2'-13C-L-Histidine has been obtained via this new scheme with high (99%) 13C incorporation starting with commercially available 13C- thiocyanate. This synthetic scheme allows access to any isotopomer of L-histidine and many other biologically important imidazole derivatives.

Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture

The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

Thiohydantoins: Selective N- and S-functionalization for Liebeskind-Srogl reaction study

Thiohydantoins formed by the Schlack-Kumpf protocol were selectively functionalized at the nitrogen, sulfur, or carbon atom to test the Liebeskind-Srogl reaction possibilities. Georg Thieme Verlag Stuttgart. New York.

Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin- 4-one (thiohydantoin) drug derivatives

Hydantoins have been known as medicinally active compounds since the 1940s and thiohydantoin derivatives are currently undergoing clinical trials as potent androgen receptor antagonist drugs. Control of solid state properties including the formation of drug polymorphs is important to the pharmaceutical industry, and frequently results from different H-bonded motifs. N-H thiohydantoins show formation of H-bonded arrays in the solid state. Two novel and five known thiohydantoin derivatives were synthesised via reaction of alkyl isothiocyanates with amino acid methyl esters. X-Ray crystallographic data were obtained for all seven compounds showing that four of the structures contain hydrogen bonded dimeric units linked via N-H...S interactions and three of the structures have N-H...O linked H-bonded chains. The Royal Society of Chemistry 2010.

Facile conversion of amino acids into 1-alkyl imidazole-2-thiones, and their oxidative desulfurization to imidazoles with benzoyl peroxide

Glycine was acylated with isothiocyanates and condensed to 3-alkyl 2-thiohydantoins, which were reduced with a mixture of sodium borohydride and lithium chloride and dehydrated to 1-alkyl imidazole-2-thiones. These were oxidatively desulfurized to imidazoles with benzoyl peroxide. No chromatography was required for model compounds. The methods developed were used to elaborate tyrosine to 1,4-di(p-methoxybenzyl)imidazole, a common intermediate in the syntheses of three imidazoles from the sponge Leucetta. Georg Thieme Verlag Stuttgart.

Synthesis of 2-Thiohydantoins and their S-Glucosylated Derivatives as Potential Antiviral and Antitumor Agents

A series of 3-alkyl-5-((Z))-arylidene-2-thiohydantoins 4a-l were synthesized from the direct condensation of the aromatic aldehydes with 3-alkyl-2-thiohydantoins 3a-c, which in turn were prepared from the reaction of glycine (1) and alkyl isothiocyanates