77358-26-0

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylisoxazole-3-carbothioamide is used as a pharmaceutical compound for its potential antibiotic, antifungal, and antitumor properties. Its unique structure and properties contribute to its potential effectiveness in treating various infections and diseases.
Used in Medicinal Chemistry Research:
5-Methylisoxazole-3-carbothioamide is used as a research compound in medicinal chemistry to explore its potential applications and mechanisms of action. Its study can lead to the development of new drugs and therapies for various medical conditions.
Used in Drug Development:
5-Methylisoxazole-3-carbothioamide is used in the development of new drugs, as its biological activity and potential therapeutic properties make it a valuable candidate for further investigation and optimization. Its unique structure can be modified to create more effective and targeted pharmaceutical agents.
Used in Antibacterial Agents:
5-Methylisoxazole-3-carbothioamide is used as an antibacterial agent, as it has shown potential in inhibiting the growth of various bacteria. Its use can contribute to the development of new antibiotics to combat antibiotic-resistant strains.
Used in Antifungal Agents:
5-Methylisoxazole-3-carbothioamide is used as an antifungal agent, as it has demonstrated potential in treating fungal infections. Its application can lead to the development of new antifungal drugs to address the growing issue of drug-resistant fungi.
Used in Antitumor Agents:
5-Methylisoxazole-3-carbothioamide is used as an antitumor agent, as it has shown potential in inhibiting the growth and proliferation of cancer cells. Its use can contribute to the development of new cancer therapies and improve patient outcomes.

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

• 175277-28-8 Ethyl 2-(5-methyl-3-isoxazolyl)-1,3-thiazole-4-carboxylate 
• 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 

Relevant academic research and scientific papers

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.