90563-93-2

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-2H-1,4-benzoxazine-2-carboxylic acid is used as a key intermediate in the synthesis of N-substituted benzomorpholine-2-carboxylic acid derivatives. These derivatives possess valuable pharmacological properties and are employed as active pharmaceutical ingredients in the development of new drugs. The synthesis of these derivatives allows for the exploration of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid serves as a versatile building block for the creation of a wide range of chemical compounds. Its unique structure and functional groups enable chemists to modify and functionalize the molecule, leading to the development of new compounds with diverse applications. This includes the synthesis of advanced materials, specialty chemicals, and other products that can be utilized across various industries.

InChI:InChI=1/C9H9NO3/c11-9(12)8-5-10-6-3-1-2-4-7(6)13-8/h1-4,8,10H,5H2,(H,11,12)/p-1/t8-/m1/s1

Upstream product

• 82756-71-6 3,4-Dihydro-2H-1,4-benzoxazin-2-carbnsaeuremethylester 
• 22244-22-0 ethyl 3,4-dihydro-2H-benzo [b][1,4]oxazine-2-carboxylate 
• 95-55-6 2-amino-phenol 

Downstream Products

• 104116-93-0 4-acetyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid 4-ethoxy-anilide 
• 104116-96-3 4-acetyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carbothioic acid 4-ethoxy-anilide 
• 1025827-87-5 (3,4-Dihydro-2H-benzo[1,4]oxazin-2-yl)-[4-(4-fluoro-phenyl)-piperazin-1-yl]-methanone 
• 92288-75-0 4-acetyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid 

Relevant academic research and scientific papers

Discovery of Dihydro-1,4-Benzoxazine Carboxamides as Potent and Highly Selective Inhibitors of Sirtuin-1

Sirtuins are signaling hubs orchestrating the cellular response to various stressors with roles in all major civilization diseases. Sirtuins remove acyl groups from lysine residues of proteins, thereby controlling their activity, turnover, and localization. The seven human sirtuins, SirT1-7, are closely related in structure, hindering the development of specific inhibitors. Screening 170,000 compounds, we identify and optimize SirT1-specific benzoxazine inhibitors, Sosbo, which rival the efficiency and surpass the selectivity of selisistat (EX527). The compounds inhibit the deacetylation of p53 in cultured cells, demonstrating their ability to permeate biological membranes. Kinetic analysis of inhibition and docking studies reveal that the inhibitors bind to a complex of SirT1 and nicotinamide adenine dinucleotide, similar to selisistat. These new SirT1 inhibitors are valuable alternatives to selisistat in biochemical and cell biological studies. Their greater selectivity may allow the development of better targeted drugs to combat SirT1 activity in diseases such as cancer, Huntington's chorea, or anorexia.