54401-85-3

Usage

Uses

Used in Pharmaceutical Applications:
Ethyl 4-pyridylacetate is used as an anticonvulsant agent for the treatment of seizures and other related conditions. Its neuropathic pain-attenuating properties make it a potential candidate for the development of medications aimed at alleviating chronic pain.
Used in Chemical Synthesis:
Ethyl 4-pyridylacetate is used as a starting material in the synthesis of various compounds, including:
1. 4-piperidylethanol, which is an important intermediate in the production of pharmaceuticals and other chemicals.
2. 4-(pyridyl) isosteres of meperidine, which are structurally similar to meperidine and may have potential applications in the development of new analgesics.
3. Ethyl-4-piperidylacetate, which is another intermediate used in the synthesis of various pharmaceuticals.
Used in Material Science:
Ethyl 4-pyridylacetate is used as a reactant in the grafting onto self-adhesive gold substrates, which may have potential applications in the development of advanced materials and coatings.
Used in Enzyme Inhibition:
Ethyl 4-pyridylacetate participates as a reagent in the synthesis of triarylethane phosphodiesterase 4 inhibitors, which are compounds that inhibit the activity of phosphodiesterase 4, an enzyme involved in various cellular processes. These inhibitors may have potential therapeutic applications in the treatment of diseases such as asthma, chronic obstructive pulmonary disease (COPD), and inflammatory bowel disease (IBD).

InChI:InChI=1/C9H11NO2/c1-2-12-9(11)7-8-3-5-10-6-4-8/h3-6H,2,7H2,1H3

Upstream product

• 28356-58-3 pyridine-4-acetic acid 
• 64-17-5 ethanol 
• 39640-62-5 2-(pyridine-4-yl)-acetamide 
• 100723-90-8 [4]pyridyl-acetic acid anilide 
• 39178-35-3 isonicotinoyl chloride hydrochloride 
• 13121-99-8 pyridin-4-ylacetonitrile 
• 124-38-9 carbon dioxide 
• 26954-25-6 (4-pyridylmethyl)lithium 
• 15854-87-2 4-iodopyridine 
• 6148-64-7 ethyl potassium malonate 
• 59576-20-4 1-phenyl-2-[4]pyridyl-ethanone-(E)-oxime 
• 13295-94-8 4-(phenylethynyl)pyridine 
• 87922-25-6 4-(α,β-dibromo-phenethyl)-pyridine 
• 100-43-6 4-vinylpyridine 

Downstream Products

• 102658-91-3 [1-(3,4-dimethoxy-phenethyl)-[4]piperidyl]-acetic acid ethyl ester 
• 92963-15-0 3t-phenyl-2-[4]pyridyl-acrylic acid ethyl ester 
• 37969-01-0 N-(3,4-dimethoxy-phenethyl)-2-pyridin-4-yl-acetamide 
• 100394-64-7 [4]pyridyl-acetic acid-(N'-phenyl-hydrazide) 
• 5344-27-4 4-(2-hydroxyethyl)pyridine 
• 39640-62-5 2-(pyridine-4-yl)-acetamide 
• 69583-00-2 pyridin-4-yl-acetic acid hydrazide 
• 152830-95-0 4-(3-(4-methoxyphenyl)-1-carbethoxypropyl)pyridine 
• 92788-10-8 rogletimide 
• 40608-77-3 2-(pyridin-4-ylmethyl)-1H-benzimidazole 
• 501-81-5 pyridyl-3-yl-acetic acid 
• 64-17-5 ethanol 
• 156093-78-6 oxo-pyridin-4-yl-acetic acid ethyl ester 
• 70199-68-7 methyl 4-pyridylacetate hydrochloride 

Relevant academic research and scientific papers

Discovery of Potent Human Glutaminyl Cyclase Inhibitors as Anti-Alzheimer’s Agents Based on Rational Design

Glutaminyl cyclase (QC) has been implicated in the formation of toxic amyloid plaques by generating the N-terminal pyroglutamate of β-amyloid peptides (pGlu-Aβ) and thus may participate in the pathogenesis of Alzheimer’s disease (AD). We designed a library of glutamyl cyclase (QC) inhibitors based on the proposed binding mode of the preferred substrate, Aβ3E?42. An in vitro structure-activity relationship study identified several excellent QC inhibitors demonstrating 5- to 40-fold increases in potency compared to a known QC inhibitor. When tested in mouse models of AD, compound 212 significantly reduced the brain concentrations of pyroform Aβ and total Aβ and restored cognitive functions. This potent Aβ-lowering effect was achieved by incorporating an additional binding region into our previously established pharmacophoric model, resulting in strong interactions with the carboxylate group of Glu327 in the QC binding site. Our study offers useful insights in designing novel QC inhibitors as a potential treatment option for AD.

Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis

We report decarboxylative carbonyl α-arylation by coupling of arylboron nucleophiles with malonic acid derivatives. This process is enabled by the merger of aerobic oxidative Cu catalysis with decarboxylative enolate interception reminiscent of malonyl-CoA reactivity in polyketide biosynthesis. This method enables the synthesis of monoaryl acetate derivatives containing electrophilic functional groups that are incompatible with existing α-arylation reactivity paradigms. The utility of the reaction is demonstrated in drug intermediate synthesis and late-stage functionalization.

Tetrazolylhydrazides as selective fragment-like inhibitors of the JumonjiC-domain-containing histone demethylase KDM4A

The JumonjiC-domain-containing histone demethylase 2A (JMJD2A, KDM4A) is a key player in the epigenetic regulation of gene expression. Previous publications have shown that both elevated and lowered enzyme levels are associated with certain types of cancer, and therefore the definite role of KDM4A in oncogenesis remains elusive. To identify a novel molecular starting point with favorable physicochemical properties for the investigation of the physiological role of KDM4A, we screened a number of molecules bearing an iron-chelating moiety by using two independent assays. In this way, we were able to identify 2-(1H-tetrazol-5-yl)acetohydrazide as a novel fragment-like lead structure with low relative molecular mass (Mr=142 Da), low complexity, and an IC50 value of 46.6 μm in a formaldehyde dehydrogenase (FDH)-coupled assay and 2.4 μm in an antibody-based assay. Despite its small size, relative selectivity against two other demethylases could be demonstrated for this compound. This is the first example of a tetrazole group as a warhead in JMJD demethylases. Anchor fragment: To develop non-promiscuous metalloenzyme inhibitors, a metal-complexing acetohydrazide group was integrated in a tetrazolyl fragment, which can be matured into a scaffold to promote further selectivity at the ligand backbone binding site of these emerging drug targets.

Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.

Inhibitors of protein kinases

Compounds of general Formula (I): wherein R1, R2, R3, Ra, A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.

Cu(I)Br-mediated preparation of 14C-labeled 3-pyridine-acetate derivatives and synthesis of a novel 14C-labeled PDE-IV inhibitor

An efficient protocol for the synthesis of 14C-labeled 3-pyridineacetate (1) and its N-oxide ([14C]2) is described. Oxidation of this pyridine ([14C]1) to its N-oxide ([ 14C]2) proceeded in high yield using H2O2 with MeReO3 as a catalyst. The reaction employs readily available diethyl [2-14C]malonate. This method has proven to be general in preparation of other pyridineacetate derivatives and their N-oxides which have been typically difficult to prepare by other means. Our development of the Cu(I)Br-coupling methodology as well as application to the synthesis of a 14C-labeled phosphodiesterase-IV (PDE-IV) inhibitor, [ 14C]3, are also reported. Copyright

Chemistry of ketoacetals: II. β,β′-Ketodiacetal and β,β′-hydroxydiacetals in reactions with amminia and amines

β,β′-Ketodiacetal and β,β′-hydroxydiacetals react with ammonium acetate in acetic acid to afford substituted pyridine, and with aromatic amines in the presence of hydrochloric acid form substituted pentamethine salts. 2005 Pleiades Publishing, Inc.

1,2-disubstituted-6-oxo-3-phenyl-piperidine-3-carboxamides and combinatorial libraries thereof

The invention relates to combinatorial libraries containing two or more novel piperidine-3-carboxamide derivative compounds, methods of preparing the piperidine-3-carboxamide derivative compounds and piperidine-3-carboxamide derivative compounds bound to a resin

Synthesis of ethoxyethynylarenes by the palladium-catalyzed reaction of aryl iodides with ethoxy(trialkylstannyl)acetylenes

Palladium-catalyzed reaction of aryl and heteroaryl iodides with ethoxy(trialkylstannyl)acetylenes gave the ethoxyethynylarenes and -heteroarenes, which were easily transformed by hydration reaction into ethyl areneacetates and heteroareneacetates.

Certain 2-carboxypiperidyl-alkylene phosphonic acids and esters thereof useful for the treatment of disorders responsive to N-methyl-D-aspartate receptor blockade

The present invention is concerned with the phosphonic acids of formula I STR1 wherein one or both of the acidic hydroxy groups of the phosphonic acid moiety may be functionalized in form of pharmaceutically acceptable mono- or di- esters; wherein Y represents optionally substituted 2-carboxypyrrolidinyl, 2-carboxy-2,5-dihydropyrrolyl, 2-carboxy-1,2,3,6-tetrahydropyridinyl, 2-carboxy-1,2,5,6-tetrahydropyridinyl, 2-carboxypiperidinyl, 2-carboxytetrahydroquinolinyl or 2-carboxyperhydroquinolinyl, 2-carboxy-2,3-dihydroindolyl or 2-carboxyperhydroindolyl as described herein, and in each of which the carboxy group may be functionalized in form of a pharmaceutically acceptable ester or amide; A represents a direct bond, lower alkenylene, lower alkylidene or lower alkylene provided that A does not represent a direct bond when Y represents 2-carboxypyrrolidinyl; and pharmaceutically acceptable salts thereof; which are useful for the treatment of nervous system disorders in mammals and as antagonists of the N-methyl-D-aspartate sensitive excitatory amino acid receptor.