3445-52-1

Basic information

• Product Name: 5-methylisoxazole-3-carboxamide
• Synonyms: 3-carbamoyl-5-methylisoxazole;5-Methyl-3-isoxazolecarboxamide;5-methyl-1,2-oxazole-3-carboxamide;NSC 18369
• CAS NO: 3445-52-1
• Molecular Formula: C₅H₆N₂O₂
• Molecular Weight: 126.12
• EINECS: 222-361-5
• Mol File: 3445-52-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 166-168℃ (water )
• Boiling Point: 292.1 °C at 760 mmHg
• Flash Point: 130.4 °C
• Appearance: /
• Density: 1.255 g/cm³
• Vapor Pressure: 0.00187mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: 2-8°C
• PKA: 14.79±0.50(Predicted)
• CAS DataBase Reference: 5-methylisoxazole-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methylisoxazole-3-carboxamide(3445-52-1)
• EPA Substance Registry System: 5-methylisoxazole-3-carboxamide(3445-52-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 3445-52-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C5H6N2O2/c1-3-2-4(5(6)8)7-9-3/h2H,1H3,(H2,6,8)

Upstream product

• 39499-34-8 5-methyl-3-isoxazolyl chloride 
• 61672-67-1 5-methyl-isoxazole-3-carbonyl azide 
• 3209-72-1 ethyl 5-methylisoxazole-3-carboxylate 
• 615-79-2 ethyl 2,4-diketopentanoate 

Downstream Products

• 57351-99-2 5-methyl-1,2-oxazole-3-carbonitrile 
• 77358-26-0 5-methyl-isoxazole-3-carbothioic acid amide 
• 196810-48-7 (S)-2-(2-Benzoyl-phenylamino)-3-(4-{2-[5-methyl-2-(5-methyl-isoxazol-3-yl)-thiazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester 
• 154016-48-5 (5-methyl-3-isoxazolyl)methylamine 
• 139443-18-8 N-(2-methoxycarbonylphenylsulphonyl)-5-methyl-isoxazole-3-carboxamide 

Relevant articles and documents

Structure-Based Drug Design of Mineralocorticoid Receptor Antagonists to Explore Oxosteroid Receptor Selectivity

The mineralocorticoid receptor (MR) is a nuclear hormone receptor involved in the regulation of body fluid and electrolyte homeostasis. In this study we explore selectivity triggers for a series of nonsteroidal MR antagonists to improve selectivity over other members of the oxosteroid receptor family. A biaryl sulfonamide compound was identified in a high-throughput screening (HTS) campaign. The compound bound to MR with pKi=6.6, but displayed poor selectivity over the glucocorticoid receptor (GR) and the progesterone receptor (PR). Following X-ray crystallography of MR in complex with the HTS hit, a compound library was designed that explored an induced-fit hypothesis that required movement of the Met852 side chain. An improvement in MR selectivity of 11- to 79-fold over PR and 23- to 234-fold over GR was obtained. Given the U-shaped binding conformation, macrocyclizations were explored, yielding a macrocycle that bound to MR with pKi=7.3. Two protein–ligand X-ray structures were determined, confirming the hypothesized binding mode for the designed compounds.