68301-99-5

Basic information

• Product Name: Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate
• Synonyms: 3-Amino-7-isopropyl-9-oxo-4-aza-9H-xanthene-2-carboxylic acid ethyl ester;Amlexanox ethyl ester;ethyl 2-amino-7-isopropyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylate;AM-5;2-Amino-7-(1-methylethyl)-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acid ethyl ester;Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate
• CAS NO: 68301-99-5
• Molecular Formula: C₁₈H₁₈N₂O₄
• Molecular Weight: 326.35
• Mol File: 68301-99-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 243-244 °C
• Boiling Point: 528.54 °C at 760 mmHg
• Flash Point: 273.452 °C
• Appearance: /
• Density: 1.286
• Vapor Pressure: 2.94E-11mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -0.16±0.20(Predicted)
• CAS DataBase Reference: Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate(68301-99-5)
• EPA Substance Registry System: Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate(68301-99-5)

Safety Data

• Hazardous Substances Data: 68301-99-5(Hazardous Substances Data)

Usage

General Description

Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate is a chemical compound with a complex molecular structure. It contains an ethyl group, an amino group, and a carboxylate group, as well as a benzopyrano and pyridine ring system. Ethyl 2-amino-7-isopropyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylate may have potential biological activity due to its unique structure, and it could be used as a building block in medicinal chemistry for the development of new drugs. Additionally, it may have applications in the field of organic synthesis and material science. However, further research is needed to fully understand the properties and potential uses of this chemical.

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 articles and documents

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.

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.