24477-36-9

Basic information

• Product Name: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-methyl-3-isoxazolecarboxamide
• Synonyms: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-methyl-3-isoxazolecarboxamide
• CAS NO: 24477-36-9
• Molecular Formula: C₁₃H₁₅N₃O₄S
• Molecular Weight: 309.3409
• Mol File: 24477-36-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-methyl-3-isoxazolecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-methyl-3-isoxazolecarboxamide(24477-36-9)
• EPA Substance Registry System: N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-methyl-3-isoxazolecarboxamide(24477-36-9)

Safety Data

• Hazardous Substances Data: 24477-36-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-2-[4-(aminosulfonyl)phenyl]ethyl-5-methyl-3-isoxazolecarboxamide is used as a reagent for the synthesis of glisoxepid (G410600), an antidiabetic drug. It plays a crucial role in the development of medications for the treatment of diabetes mellitus type 2.
Glisixepid, synthesized using N-2-[4-(aminosulfonyl)phenyl]ethyl-5-methyl-3-isoxazolecarboxamide, is a sulfonylurea derivative that helps in managing blood sugar levels in patients with type 2 diabetes. It works by stimulating the release of insulin from the pancreas, thereby improving the body's ability to regulate glucose levels.

Upstream product

• 39499-34-8 5-methyl-3-isoxazolyl chloride 
• 6325-22-0 chlorhydrate de (β-aminoethyl)-4 benzenesulfonamide 
• 85-44-9 phthalic anhydride 
• 25046-79-1 glisoxepide 
• 35303-76-5 4-(2-aminoethyl)benzenesulfonamide 
• 3405-77-4 5-methylisoxazole 3-carboxylic acid 

Downstream Products

• 24477-37-0 5-methyl-isoxazole-3-carboxylic acid 4-(cyclohexylcarbamoyl-sulfamoyl)-phenethylamide 
• 30081-28-8 5-methyl-isoxazole-3-carboxylic acid 4-[(N',N'-dimethyl-hydrazinocarbonyl)-sulfamoyl]-phenethylamide 
• 24489-11-0 5-methyl-isoxazole-3-carboxylic acid 4-[(cyclohexylmethyl-carbamoyl)-sulfamoyl]-phenethylamide 
• 24501-20-0 1,8,8-trimethyl-3-aza-bicyclo[3.2.1]octane-3-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 52320-21-5 5-methyl-isoxazole-3-carboxylic acid 4-[(4-tert-butyl-cyclohexylcarbamoyl)-sulfamoyl]-phenethylamide 
• 24489-12-1 5-methyl-isoxazole-3-carboxylic acid 4-[(2-cyclohex-1-enyl-ethylcarbamoyl)-sulfamoyl]-phenethylamide 
• 24489-16-5 decahydro-4,7-ethano-cyclobuta[f]isoindole-2-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 24489-18-7 5-methyl-isoxazole-3-carboxylic acid 4-(pyrrolidine-1-carbonylsulfamoyl)-phenethylamide 
• 24489-03-0 5-methyl-isoxazole-3-carboxylic acid 4-(cyclopentylcarbamoyl-sulfamoyl)-phenethylamide 
• 24489-19-8 piperidine-1-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 24489-20-1 azepane-1-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 24489-21-2 morpholine-4-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 
• 24489-14-3 5-methyl-isoxazole-3-carboxylic acid 4-(cycloheptylcarbamoyl-sulfamoyl)-phenethylamide 
• 24489-22-3 4-methyl-piperazine-1-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide 

Relevant articles and documents

NOVEL COMPOUNDS AND USES

The present invention relates to compounds of formula (I): wherein Q is O or S; R1 is a cyclic group substituted with at least one group X, wherein R1 may optionally be further substituted; X is any group comprising a carbonyl group; and R2 is a cyclic group substituted at the α-position, wherein R2 may optionally be further substituted. The present invention further relates to salts, solvates and prodrugs of such compounds, to pharmaceutical compositions comprising such compounds, and to the use of such compounds in the treatment and prevention of medical disorders and diseases, most especially by the dual action of NLRP3 inhibition and the stimulation of insulin secretion.

Sulfonylureas as Concomitant Insulin Secretagogues and NLRP3 Inflammasome Inhibitors

Insulin-secretory sulfonylureas are widely used, cost-effective treatments for type 2 diabetes (T2D). However, pancreatic β-cells are continually depleted as T2D progresses, thereby rendering the sulfonylurea drug class ineffective in controlling glycaemia. Dysregulation of the innate immune system via activation of the NLRP3 inflammasome, and the consequent production of interleukin-1β, has been linked to pancreatic β-cell death and multiple inflammatory complications of T2D disease. One proposed strategy for treating T2D is the use of sulfonylurea insulin secretagogues that are also NLRP3 inhibitors. We report the synthesis and biological evaluation of nine sulfonylureas that inhibit NLRP3 activation in murine bone-marrow- derived macrophages in a potent, dose-dependent manner. Six of these compounds inhibited NLRP3 at nanomolar concentrations and can also stimulate insulin secretion from a murine pancreatic cell line (MIN6). These novel compounds possess unprecedented dual modes of action, paving the way for a new generation of sulfonylureas that may be useful as therapeutic candidates and/or tool compounds in T2D and its associated inflammatory complications.

SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME

ABSTRACT The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.