95306-61-9

Basic information

• Product Name: 4-(benzylamino)pyridin-2(1H)-one
• Synonyms: 4-(benzylamino)pyridin-2(1H)-one
• CAS NO: 95306-61-9
• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200
• Mol File: 95306-61-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(benzylamino)pyridin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(benzylamino)pyridin-2(1H)-one(95306-61-9)
• EPA Substance Registry System: 4-(benzylamino)pyridin-2(1H)-one(95306-61-9)

Safety Data

• Hazardous Substances Data: 95306-61-9(Hazardous Substances Data)

Usage

Description

4-(Benzylamino)pyridin-2(1H)-one is an organic compound with the chemical formula C11H10N2O. It is a derivative of pyridin-2(1H)-one, featuring a benzylamino group attached to the 4-position of the pyridine ring. 4-(benzylamino)pyridin-2(1H)-one exhibits unique structural and functional properties, making it a versatile building block in organic synthesis and a potential candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
4-(Benzylamino)pyridin-2(1H)-one is used as a key intermediate in the synthesis of various bioactive molecules, including peptidomimetics and other drug candidates. Its unique structure allows for the development of compounds with specific binding affinities and selectivity towards biological targets.
Used in Anticancer Agents Development:
4-(Benzylamino)pyridin-2(1H)-one is used as a building block in the development of peptidomimetics containing a boronic acid moiety. These peptidomimetics are designed to target the 20S proteasome, a crucial enzyme complex involved in cellular protein degradation and a validated target for cancer therapy. By inhibiting the proteasome, these peptidomimetics can disrupt the cellular machinery of cancer cells, leading to their growth arrest and eventual death.

Upstream product

• 626-03-9 4-hydroxy-2-pyridone 
• 100-46-9 benzylamine 
• 53937-02-3 4-(benzyloxy)pyridin-2(1H)-one 
• 1624283-59-5 N-benzyl-2-(benzyloxy)pyridin-4-amine 
• 960298-00-4 2-(benzyloxy)-4-bromopyridine 

Downstream Products

• 1624283-65-3 ethyl 2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetate 
• 1624283-91-5 (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid pinanediol ester 
• 1624283-35-7 (R)-1-{2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetamido}-3-methylbutylboronic acid 
• 1624283-78-8 2-[4-(benzylamino)-2-oxopyridin-1(2H)-yl]acetic acid 
• 38767-72-5 3-deazaC 

Relevant articles and documents

Development of novel selective peptidomimetics containing a boronic acid moiety, targeting the 20s proteasome as anticancer agents

This paper describes the design, synthesis, and biological evaluation of peptidomimetic boronates as inhibitors of the 20S proteasome, a validated target in the treatment of multiple myeloma. The synthesized compounds showed a good inhibitory profile against the ChT-L activity of 20S proteasome. Compounds bearing a β-alanine residue at the P2 position were the most active, that is, 3-ethylphenylamino and 4-methoxyphenylamino (R)-1-{3-[4-(substituted)-2- oxopyridin-1(2H)-yl]propanamido}-3-methylbutylboronic acids (3 c and 3 d, respectively), and these derivatives showed inhibition constants (Ki) of 17 and 20 nM, respectively. In addition, they co-inhibited post glutamyl peptide hydrolase activity (3 c, Ki=2.57 μM; 3 d, K i=3.81 μM). No inhibition was recorded against the bovine pancreatic α-chymotrypsin, which thus confirms the selectivity towards the target enzyme. Docking studies of 3 c and related inhibitors into the yeast proteasome revealed the structural basis for specificity. The evaluation of growth inhibitory effects against 60 human tumor cell lines was performed at the US National Cancer Institute. Among the selected compounds, 3 c showed 50 % growth inhibition (GI50) values at the sub-micromolar level on all cell lines.

A General Route to 5- and 6-Substituted 4-Amino-2-oxo-1,2-dihydropyridines

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