404-52-4

Usage

Uses

Used in Neuropharmacology:
U 19963 is used as a neuroprotective agent for its potential in treating neurological disorders such as Parkinson's disease and epilepsy. Its neuroprotective effects and anti-seizure activity make it a promising candidate for further research and development in this field.
Used in Drug Development for Neurological Disorders:
U 19963 is used as a potential therapeutic agent for the treatment of neurological disorders, given its demonstrated efficacy in preclinical studies. Its role as a quinolinic acid receptor antagonist contributes to its potential in managing the symptoms and progression of these disorders.
Used in Psychiatry:
U 19963 is used as a potential treatment for anxiety and depression, as it has shown promising results in animal models. Its investigation in this area suggests that it may offer new avenues for managing these mental health conditions.
Used in Preclinical Research:
U 19963 is used as a subject of study in preclinical research to explore its mechanisms of action, efficacy, and safety profile. This research is crucial for understanding its potential applications and for guiding future clinical trials and therapeutic development.

InChI:InChI=1/C13H10F2N2S/c14-9-1-5-11(6-2-9)16-13(18)17-12-7-3-10(15)4-8-12/h1-8H,(H2,16,17,18)

Upstream product

• 1544-68-9 4-fluorophenyl isothiocyanate 
• 371-40-4 4-fluoroaniline 
• 75-15-0 carbon disulfide 

Downstream Products

• 10018-32-3 N-(4-fluoro-phenyl)-oxalomonoimidic acid-(4-fluoro-anilide)-nitrile 
• 348-41-4 6-fluoro-N-(4-fluorophenyl)benzo[d]thiazol-2-amine 
• 351-74-6 bis(4-fluorophenyl)methanediimine 
• 1544-68-9 4-fluorophenyl isothiocyanate 
• 51964-15-9 3-(4-fluorophenyl)-2-(4-fluorophenylimino)-1,3-thiazolidine-4-one 
• 51964-22-8 3-(4-fluoro-phenyl)-thiazolidine-2,4-dione 
• 370-22-9 N,N'-Di-(4-Fluorphenyl)-harnstoff 
• 1434158-86-7 N,1-bis(4-fluorophenyl)-1H-tetrazol-5-amine 
• 1434158-93-6 N,4-bis(4-fluorophenyl)-4H-1,2,4-triazol-3-amine 
• 146680-56-0 N,N’-bis(4’-fluorophenyl)imidazolidine-2-thione-4,5-dione 
• 678562-00-0 4-{5-[3-(4-Fluoro-phenyl)-2-[(Z)-4-fluoro-phenylimino]-4-oxo-thiazolidin-(5E)-ylidenemethyl]-furan-2-yl}-benzoic acid 
• 1352834-05-9 4-[3-(4-fluorophenyl)-2-(4-fluorophenylimino)-4-oxothiazolidin-5-ylidenemethyl]benzoic acid 
• 350-11-8 N-(4-fluoro-phenyl)-2-thio-oxalomonoimidic acid-1-(4-fluoro-anilid)-2-amide 
• 366-11-0 N-(2,5-dimethoxy-phenyl)-N'-(4-fluoro-phenyl)-thiourea 

Relevant academic research and scientific papers

Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water

ABATRACT: A direct approach to N,N′-disubstituted urea/thiourea from the self-condensation reactions of isothiocyanates in water has been developed. This access tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to N,N′-disubstituted urea/thiourea in moderate to excellent yields from safe and easily available starting materials. A plausible mechanism of the desulfurization self-condensation reaction for urea was also proposed and the role of di-tert-butyl peroxide (DTBP) and copper catalyst in the present strategy was demonstrated with the help of ESI mass spectrometry of intermediate studies.

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

Novel non-peptidic small molecule inhibitors of secreted aspartic protease 2 (SAP2) for the treatment of resistant fungal infections

Targeting secreted aspartic protease 2 (SAP2), a kind of virulence factor, represents a new strategy for antifungal drug discovery. In this report, the first-generation of small molecule SAP2 inhibitors was rationally designed and optimized using a structure-based approach. In particular, inhibitor 23h was highly potent and selective and showed good antifungal potency for the treatment of resistant Candida albicans infections.

Palladium catalyzed carbonylative annulation of the C(sp2)-H bond of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-triazol-3-amines to quinazolinones

Pd(ii) catalyzed direct C-H carbonylative annulation of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-1,2,4-triazol-3-amines gave the corresponding triazole and tetrazole fused quinazolinones in good yields. This methodology offers a convenient method for the synthesis of these important heterocyclic scaffolds in a highly atom economical process. On the mechanistic aspect weakly nucleophilic triazole and tetrazole moieties function as both directing as well as intramolecular nucleophiles. The catalytically active C-H activated intermediate dimeric Pd complex was isolated and characterized which on exposure to CO gas gave the corresponding tetrazole fused quinazolinone derivative. On the basis of isolation of the intermediate and observed kinetic isotope effects, a mechanism has been proposed for the C-H activated direct carbonylative annulation reaction.

Nickle Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions

An efficient synthesis of thiazolidine-2,4,5-triimine derivatives was developed via Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide insertion reactions.

An Environment-friendly Synthesis of 2,3-Disubstituted-2-iminothiazoline-4-ones

A series of 2,3-substituted-2-iminothiazoline-4-ones derivatives have been synthesized via an improved method including an auto-catalyzed reaction. This method avoided using any extra catalyst except for the reaction material. This method has been successful in both the aromatic substituted 2-iminothiazolines and the alkyl substituted 2-iminothiazolines. The special product with a hydroxyl group on the 2-iminogroup of 1,3-thiazoline-4-ones has also been obtained unexpectedly. The possible mechanism has been proposed for the special process of dealkylation and hydroxylation. This method offered a special way to afford the 2-hydroxyimino-substituted thiazoline-4-one derivatives in an efficient and eco-friendly way. The mechanism of the transformation under acid condition has also been proposed.

Synthesis and biological evaluation of 2-arylimino-3-pyridin-thiazolineone derivatives as antibacterial agents

With an intention to find more potent antibacterial agents, four halogen disubstituted thiazolineone derivatives (2a-d), five halogen monosubstituted thiazolineone derivatives (2e-i), and eleven 2-arylimino-3-pyridin-thiazolineone derivatives (2j-t) were

Synthesis of novel 4-thiazolidione derivatives as antibacterial agents against drug-resistant Staphylococcus epidermidis

A series of novel substituted 4-thiazolidione derivatives were designed, synthesized, and evaluated in vitro for their antibacterial activities, in comparison with methicillin and ampicillin. Compounds (7d, 7h-k) exhibit good potency in inhibiting the growth of Staphylococcus epidermidis (MIC: 1.57-3.13 μM). Further antibacterial effects of compounds (7d, 7h-k) were investigated using clinical isolates (methicillin-resistant Staphylococcus epidermidis and methicillin-resistant Staphylococcus aureus), in comparison with methicillin and levofloxacin. Compound 7k showed the most potent antibacterial activities among the synthesized compounds.

Synthesis and biological evaluation of halogenated 2-arylimino-3- arythiazolidine-4-ones containing benzoic acid fragments as antibacterial agents

A series of halogenated 2-arylimino-3-ary-thiazolidine-4-ones containing (5-furan-2-yl)-benzoic acid or (5-thiophene-2-yl)-benzoic acid fragments was synthesized, and evaluated in vitro for their antibacterial activity, antibiofilm activity, erythrocyte h

A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents

The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.