68301-99-5

Usage

Uses

Used in Medicinal Chemistry:
Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate is used as a building block for the development of new drugs due to its complex molecular structure and potential biological activity.
Used in Organic Synthesis:
In the field of organic synthesis, Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate is utilized as a key intermediate for the synthesis of various organic compounds, leveraging its reactive functional groups and ring systems.
Used in Material Science:
Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate may be employed in material science for the creation of novel materials, potentially due to its structural features that could influence material properties such as stability, reactivity, or selectivity.
Further research is essential to fully understand the properties and potential applications of Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate across different industries.

InChI:InChI=1/C18H18N2O4/c1-4-23-18(22)13-8-12-15(21)11-7-10(9(2)3)5-6-14(11)24-17(12)20-16(13)19/h5-9H,4H2,1-3H3,(H2,19,20)

Upstream product

• 50743-32-3 6-isopropyl-4-oxo-4H-1-benzopyran-3-carbonitrile 
• 105-56-6 ethyl 2-cyanoacetate 
• 68302-57-8 amlexanox 
• 64-17-5 ethanol 

Downstream Products

• 68302-57-8 amlexanox 

Relevant academic research and scientific papers

Carboxylic acid derivatives of amlexanox display enhanced potency toward TBK1 and IKK? and reveal mechanisms for selective inhibition

Chronic low-grade inflammation is a hallmark of obesity, which is a risk factor for the development of type 2 diabetes. The drug amlexanox inhibits IkB kinase ? (IKK?) and TANK binding kinase 1 (TBK1) to promote energy expenditure and improve insulin sensitivity. Clinical studies have demonstrated efficacy in a subset of diabetic patients with underlying adipose tissue inflammation, albeit with moderate potency, necessitating the need for improved analogs. Herein we report crystal structures of TBK1 in complex with amlexanox and a series of analogs that modify its carboxylic acid moiety. Removal of the carboxylic acid or mutation of the adjacent Thr156 residue significantly reduces potency toward TBK1, whereas conversion to a short amide or ester nearly abolishes the inhibitory effects. IKK? is less affected by these modifications, possibly due to variation in its hinge that allows for increased conformational plasticity. Installation of a tetrazole carboxylic acid bioisostere improved potency to 200 and 400 nM toward IKK? and TBK1, respectively. Despite improvements in the in vitro potency, no analog produced a greater response in adipocytes than amlexanox, perhaps because of altered absorption and distribution. The structure-activity relationships and cocrystal structures described herein will aid in future structure-guided inhibitor development using the amlexanox pharmacophore for the treatment of obesity and type 2 diabetes.

Compound for improving sensitivity of PCa drug-resistant cells to antagonists and application of compound

The invention discloses a compound for improving the sensitivity of PCa drug-resistant cells to antagonists and application of the compound. The structural formula of the compound is shown in the invention; after enzalutamide and the compound are co-cultured, the cell viability is obviously influenced, it indicates that the compounds improve the sensitivity of prostate cancer drug-resistant cellsto enzalutamide. Therefore, the compound can be applied to preparation of drugs for improving the sensitivity of prostate cancer drug-resistant cells to androgen receptor antagonists such as enzalutamide.

Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines

5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe 2 OH, H NHOMe. On the other hand, in the tetrazole series, 2-unsubsitituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress.