33631-01-5

Usage

Uses

Used in Organic Synthesis:
3-Amino-1-methylpyridin-2(1H)-one is utilized as a key intermediate in organic synthesis for the production of a wide range of chemical compounds. Its structural features facilitate its reactivity and compatibility with other molecules, making it a preferred choice for constructing complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Amino-1-methylpyridin-2(1H)-one serves as a valuable building block for the development of new drugs. Its presence in the molecular structure can influence the pharmacological properties of the resulting compounds, such as their potency, selectivity, and bioavailability.
Used in Drug Development:
3-Amino-1-methylpyridin-2(1H)-one is employed as a component in the formulation of new drugs, particularly in the design of novel therapeutic agents. Its incorporation into drug molecules can enhance their efficacy and safety profiles, contributing to the advancement of medical treatments for various diseases and conditions.
Used in Material Science:
3-Amino-1-methylpyridin-2(1H)-one also finds applications in material science, where it is used to develop new materials with specific properties. Its ability to form stable complexes and interact with other molecules makes it suitable for creating materials with tailored characteristics for use in various industries, such as electronics, coatings, and adhesives.

InChI:InChI=1/C6H8N2O/c1-8-4-2-3-5(7)6(8)9/h2-4H,7H2,1H3

Upstream product

• 32896-91-6 1-methyl-3-nitropyridin-2(1H)-one 
• 6332-56-5 3-nitropyridone 

Relevant academic research and scientific papers

Pyrrolopyrimidine derivative as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and provides a compound shown as a general formula (I), geometric isomers or pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof, and preparation methods thereof, wherein A, B and R1 are described in the claims and the specification. The compound and the geometric isomer thereof or the pharmaceutically acceptable salt, hydrate, solvate, prodrug or pharmaceutical composition thereof have the activity as a protein kinase inhibitor, especially an FAK kinase inhibitor.

Palladium-catalyzed directed synthesis ofortho-deuterated phenylacetic acid and analogues

The synthesis of deuterium-labeled organic compounds is of increased interest, especially after the approval of deutetrabenazine by the Food and Drug Administration in 2014. The selective incorporation of deuterium in the place of hydrogen not only represents uniqueness in terms of a novel chemical class, but it also can improve the pharmacokinetic profiles of drug molecules while retaining potency and other parameters; thus, hydrogen-deuterium (H/D) exchange methods have been proven to be powerful additions in different areas of chemical science. In that regard, metal-catalyzed deuterium labelingviaC-H activation mediated by a unique inbuilt directing group (DG) can play a significant role in the synthesis of novel deuterated chemical entities. In this context, herein, we divulge our results relating to Pd(ii)-catalyzed deuterium incorporation (>97%) at the γ C(sp2)-position of pyridone-containing phenylacetic acid derivatives, where 3-amino-1-methyl-1H-pyridin-2-one (AMP) not only acts as an efficientN,O-directing group, but it also constitutes a part of the target molecules of medicinal importance. Our methodology, which has been optimized based on the effects of temperature, catalyst, time, and substrate scope, shows advantages over existing protocols, with non-selectivity or meager deuteration or the use of an expensive metal (catalytic or super stoichiometric) and a deuterated solvent, reported previously for the deuteration of phenylacetic acid and its derivatives. Moreover, towards our aim of synthesizing deuterium-labeled biologically relevant compounds, the gram scale synthesis of a deuterated analogue of biphenyl acetic acid (3), known to have activity against epileptic seizures, has also been successfully accomplished in high yields and with excellent isotope enrichmentviaimplementing this protocol.

Design, synthesis and biological evaluation of novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potential FAK inhibitors and anticancer agents

A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives possessing a dimethylphosphine oxide moiety were designed, synthesized and evaluated as novel Focal adhesion kinase (FAK) inhibitors. Most compounds potently suppressed the enzymatic activities of FAK, with IC50 values in the 10?8–10?9 M range, and potently inhibited the proliferation of breast (MDA-MB-231) and lung (A549) cancer cell lines. The representative compound 25b exhibited potent enzyme inhibition (IC50 = 5.4 nM) and good selectivity when tested on a panel of 26 kinases. 25b exhibited antiproliferative activity against A549 cells (IC50 = 3.2 μM) and relatively less cytotoxicity to a normal human cell line HK2. Compound 25b also induced apoptosis and suppressed the migration of A549 cells in a concentration-dependent manner. Further profiling of compound 25b revealed it had good metabolic stability in mouse, rat and human liver microsomes in vitro and showed weak inhibitory activity against various subtypes of human cytochrome P450. The docking study of compound 25b was performed to elucidate its possible binding modes and to provide a structural basis for further structure-guided design of FAK inhibitors.

3-Amino-1-methyl-1 H-pyridin-2-one-Directed PdII Catalysis: C(sp3)-H Activated Diverse Arylation Reaction

A new bidentate directing group, 3-amino-1-methyl-1H-pyridin-2-one, is introduced to achieve a powerful PdII metallacycle for selective γ-C(sp3)-H activation and arylation of aromatic and aliphatic carboxylic acid derivatives. The versatility of the directing group is validated for remote arylation of β-C(sp3)-H, β-C(sp2)-H, and γ-C(sp2)-H to achieve therapeutically important 2-pyridone analogues and arylated acid synthons. The traceless removal of the directing group to retrieve the directing element and carboxylic acids makes this method more interesting.

Discovery of new nanomolar inhibitors of GPa: Extension of 2-oxo-1,2-dihydropyridinyl-3-yl amide-based GPa inhibitors

Glycogen Phosphorylase (GP) is a functionally active dimeric enzyme, which is a target for inhibition of the conversion of glycogen to glucose-1-phosphate. In this study we report the design and synthesis of 14 new pyridone derivatives, and seek to extend the SAR analysis of these compounds. The SAR revealed the minor influence of the amide group, importance of the pyridone ring both spatially around the pyridine ring and for possible π-stacking, and confirmed a preference for inclusion of 3,4-dichlorobenzyl moieties, as bookends to the pyridone scaffold. Upon exploring a dimer strategy as part of the SAR analysis, the first extended 2-oxo-dihydropyridinyl-3-yl amide nanomolar based inhibitors of GPa (IC50?=?230 and 260?nM) were identified.

REDUCTION OF HETERO-AROMATIC NITRO COMPOUNDS WITH BAKER'S YEAST

Reduction of nitro group on hetero-aromatics with baker's yeast has been examined.