4461-29-4

Usage

Uses

Used in Pharmaceutical Industry:
THIOPHENE-2-ACETAMIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of novel drugs with potential therapeutic applications.
Used in Positron Emission Tomography (PET) Imaging:
THIOPHENE-2-ACETAMIDE is used in the preparation of [18F]Maleimide-based Glycogen synthase kinase-3β (GSK-3β) ligands. These ligands are essential for PET imaging, a non-invasive medical imaging technique that helps visualize the metabolic processes within the body. By targeting GSK-3β, a protein involved in various cellular functions and diseases, THIOPHENE-2-ACETAMIDE can contribute to the early detection and monitoring of conditions related to GSK-3β dysregulation.

InChI:InChI=1/C6H7NOS/c7-6(8)4-5-2-1-3-9-5/h1-3H,4H2,(H2,7,8)

Upstream product

• 1918-82-7 2-vinylthiophene 
• 20893-30-5 2-cyanomethylthiophene 
• 88-15-3 2-Acetylthiophene 
• 39098-97-0 2-thienylacetic acid chloride 
• 19432-68-9 methyl 2-thiopheneacetate 
• 115510-91-3 1-(thien-2-yl)ethanol 
• 123-91-1 1,4-dioxane 
• 6319-47-7 5-(2'-thiophenemethylene)rhodamine 
• 139109-61-8 2-hydroxyimino-3-[2]thienyl-propionic acid 
• 765-50-4 2-Chloromethylthiophene 
• 7625-53-8 rac-Ala-OMe 
• 89677-36-1 3-thiophen-2-yl-2-thioxo-propionic acid 
• 1918-77-0 Thiophene-2-acetic acid 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 20893-30-5 2-cyanomethylthiophene 
• 1003-31-2 thiophene-2-carbonitrile 
• 349426-88-6 N-(2-ethylphenyl)-2-(thiophen-2-yl)acetamide 
• 69047-43-4 2-(thiophen-2-yl)-N-(o-tolyl)acetamide 
• 346663-54-5 2-(thiophen-2-yl)-N-(p-tolyl)acetamide 
• 27757-85-3 2-Aminomethylthiophene 
• 30433-91-1 [2-(2-thyenyl)ethyl]amine 

Relevant academic research and scientific papers

A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids

Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

[18F]MALEIMIDE-BASED GLYCOGEN SYNTHASE KINASE-3BETA LIGANDS FOR POSITRON EMISSION TOMOGRAPHY IMAGING AND RADIOSYNTHESIS METHOD

The present invention provides a compound having the structure: (Formula I), and a method of inhibiting Glycogen synthase kinase-3 β (GSK-3β) in a subject comprising administering to the subject said compound, so as to thereby inhibit the GSK-3β in the subject.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.

Synthesis method of 2-thienylmethylamine

The invention relates to a synthesis method of 2-thienylmethylamine. According to the method, raw materials of 2-acetylthiophene, ethyl alcohol, concentrated ammonia water and sulphur powder take a reaction under the condition of 0.08 to 2.00 MPa to produce the 2-thienylacetamide; the 2-thienylacetamide and sodium hypochlorite or sodium hypobromite are prepared into 2-thienylmethylamine through Hofmann degradation under the effect of liquid caustic soda. The synthesis method has the advantages that the raw materials can be easily obtained; the process is simple and controllable; the maneuverability is high; the purity of the prepared finished product is high; the yield is high.

Phosphinous Acid-Assisted Hydration of Nitriles: Understanding the Controversial Reactivity of Osmium and Ruthenium Catalysts

The synthesis and catalytic behavior of the osmium(II) complexes [OsCl2(η6-p-cymene)(PR2OH)] [R=Me (2 a), Ph (2 b), OMe (2 c), OPh (2 d)] in nitrile hydration reactions is presented. Among them, the best catalytic results were obtained with the phosphinous acid derivative [OsCl2(η6-p-cymene)(PMe2OH)] (2 a), which selectively provided the desired primary amides in excellent yields and short times at 80 °C, employing directly water as solvent, and without the assistance of any basic additive (TOF values up to 200 h?1). The process was successful with aromatic, heteroaromatic, aliphatic, and α,β-unsaturated organonitriles, and showed a high functional group tolerance. Indeed, complex 2 a represents the most active and versatile osmium-based catalyst for the hydration of nitriles reported so far in the literature. In addition, it exhibits a catalytic performance similar to that of its ruthenium analogue [RuCl2(η6-p-cymene)(PMe2OH)] (4). However, when compared to 4, the osmium complex 2 a turned out to be faster in the hydration of less-reactive aliphatic nitriles, whereas the opposite trend was generally observed with aromatic substrates. DFT calculations suggest that these differences in reactivity are mainly related to the ring strain associated with the key intermediate in the catalytic cycle, that is, a five-membered metallacyclic species generated by intramolecular addition of the hydroxyl group of the phosphinous acid ligand to the metal-coordinated nitrile.

Chlorophosphines as auxiliary ligands in ruthenium-catalyzed nitrile hydration reactions: Application to the preparation of β-ketoamides

The catalytic hydration of nitriles into amides, in water under neutral conditions, has been studied using a series of arene-ruthenium(ii) complexes containing commercially available chlorophosphines as auxiliary ligands, i.e. compounds [RuCl2(η6-p-cymene)(PR2Cl)] (R = aryl, heteroaryl or alkyl group). In the reaction medium, the coordinated chlorophosphines readily undergo hydrolysis to generate the corresponding phosphinous acids PR2OH, which are well-known "cooperative" ligands for this catalytic transformation. Among the complexes employed, best results were obtained with [RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}]. Performing the catalytic reactions at 40 °C with 2 mol% of this complex, a large variety of organonitriles could be selectively converted into the corresponding primary amides in high yields and relatively short times. The application of [RuCl2(η6-p-cymene){P(4-C6H4F)2Cl}] in the preparation of synthetically useful β-ketoamides is also presented.

Supported Gold Nanoparticles-Catalyzed Microwave-Assisted Hydration of Nitriles to Amides under Base-Free Conditions

Polystyrene-supported gold (Au@PS) nanoparticles were synthesized by the reduction deposition approach and well characterized by UV-visible, XRD, TEM, SAED, EDX, and XPS studies. The Au@PS was applied as catalyst for the hydration of nitriles to amides in water under microwave irradiation. Several functionalized aromatic, heterocyclic and aliphatic nitriles were found to be active for synthesis of the corresponding amides where no activation of water by base, ligand and support is needed. Easy recovery, negligible leaching and recyclability for up to eight runs are added advantages of the catalyst under water-mediated reaction conditions. (Figure presented.).

Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions

Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.