77358-26-0

Basic information

• Product Name: 5-METHYLISOXAZOLE-3-CARBOTHIOAMIDE
• Synonyms: 5-METHYLISOXAZOLE-3-CARBOTHIOAMIDE;3-Isoxazolecarbothioamide,5-methyl-(9CI);5-METHYLISOXAZOLE-3-THIOCARBOXAMIDE;5-Methylisoxazole-3-carbothioic acid amide;5-Methyl-3-isoxazolecarbothioamide;5-Methylthio-3-isoxazolecarboxamide;5-Methylisoxazole-3-carbothioic acid amide, 3-Carbamothioyl-5-methyl-1,2-oxazole
• CAS NO: 77358-26-0
• Molecular Formula: C₅H₆N₂OS
• Molecular Weight: 142.18
• Product Categories: THIOAMIDE
• Mol File: 77358-26-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 169 °C
• Boiling Point: 305℃
• Flash Point: 139℃
• Appearance: /
• Density: 1.312
• Vapor Pressure: 0.000822mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 5-METHYLISOXAZOLE-3-CARBOTHIOAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLISOXAZOLE-3-CARBOTHIOAMIDE(77358-26-0)
• EPA Substance Registry System: 5-METHYLISOXAZOLE-3-CARBOTHIOAMIDE(77358-26-0)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• Hazardous Substances Data: 77358-26-0(Hazardous Substances Data)

Usage

General Description

5-Methylisoxazole-3-carbothioamide is a chemical compound with the molecular formula C5H6N2OS. It is a sulfur-containing heterocyclic compound that belongs to the class of isoxazoles. 5-METHYLISOXAZOLE-3-CARBOTHIOAMIDE has potential pharmaceutical applications, particularly in the field of medicinal chemistry, as it exhibits biological activity. 5-Methylisoxazole-3-carbothioamide has been studied for its potential antibiotic, antifungal, and antitumor properties. Its structure and properties make it a promising candidate for further research and development in the pharmaceutical industry.

InChI:InChI=1/C5H6N2OS/c1-3-2-4(5(6)9)7-8-3/h2H,1H3,(H2,6,9)

Upstream product

• 57351-99-2 5-methyl-1,2-oxazole-3-carbonitrile 
• 3445-52-1 5-methyl-isoxazole-3-carbothioic acid amide 

Downstream Products

• 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 
• 77358-59-9 3-Isopropyl-6-(5-methyl-3-isoxazolyl)-2-phenyl-2,3-dihydro-4H-1,3,5-thiadiazin-4-on 
• 175277-28-8 Ethyl 2-(5-methyl-3-isoxazolyl)-1,3-thiazole-4-carboxylate 

Relevant articles and documents

N-(2-benzoylphenyl)-L-tyrosine PPARγ agonists. 2. Structure-activity relationship and optimization of the phenyl alkyl ether moiety

We previously reported the identification of (2S)-((2- benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-phenyloxazol-4- yl)ethoxy]phenyl}propanoic acid (2) (PPARγ pK(i) = 8.94, PPARγ pEC50 = 9.47) as a potent and selective PPARγ agonist. We now report the expanded structure-activity relationship around the phenyl alkyl ether moiety by pursuing both a classical medicinal chemistry approach and a solid-phase chemistry approach for analogue synthesis. The solution-phase strategy focused on evaluating the effects of oxazole and phenyl ring replacements of the 2-(5-methyl-2-phenyloxazol-4-yl)ethyl side chain of 2 with several replacements providing potent and selective PPARγ agonists with improved aqueous solubility. Specifically, replacement of the phenyl ring of the phenyloxazole moiety with a 4-pyridyl group to give 2(S)-((2- benzoylphenyl)amino)-3-{4-[2-(5-methyl-2-pyridin-4-yloxazol-4- yl)ethoxy]phenyl}propionic acid (16) (PPARγ pK(i) = 8.85, PPARγ pEC50 = 8.74) or a 4-methylpiperazine to give 2(S)-((2-benzoylphenyl)amino)-3-(4- {2-[5-methyl-2-(4-methylpiperazin-1-yl)thiazol-4-yl]ethoxy}phenyl)propionic acid (24) (PPARγ pK(i) = 8.66, PPARγ pEC50 = 8.89) provided two potent and selective PPARγ agonists with increased solubility in pH 7.4 phosphate buffer and simulated gastric fluid as compared to 2. The second strategy took advantage of the speed and ease of parallel solid-phase analogue synthesis to generate a more diverse set of phenyl alkyl ethers which led to the identification of a number of novel, high-affinity PPARγ ligands (PPARγ pK(i)'s 6.98-8.03). The combined structure-activity data derived from the two strategies provide valuable insight on the requirements for PPARγ binding, functional activity, selectivity, and aqueous solubility.