14441-90-8

Usage

Uses

Used in Pharmaceutical Industry:
5-Phenylisoxazole-3-carboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to exhibit anti-inflammatory, antimicrobial, and antitumor properties. Its incorporation into drug molecules can lead to the development of new treatments for a range of diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Phenylisoxazole-3-carboxylic acid is utilized as a building block in the creation of agrochemicals, leveraging its biological activities to develop compounds that can protect crops from diseases and pests, thereby enhancing agricultural productivity.
Used in Organic Synthesis:
5-Phenylisoxazole-3-carboxylic acid serves as a valuable reagent in organic synthesis, contributing to the formation of a wide array of chemical compounds that can be applied across various industries, from pharmaceuticals to materials science.
Used in Medicinal Chemistry Research:
As a research tool in medicinal chemistry, 5-Phenylisoxazole-3-carboxylic acid aids scientists in studying the structure-activity relationships of potential drug candidates. Its use in research facilitates the advancement of knowledge in drug design and the optimization of therapeutic agents.

InChI:InChI=1/C10H7NO3/c12-10(13)8-6-9(14-11-8)7-4-2-1-3-5-7/h1-6H,(H,12,13)/p-1

Upstream product

• 7063-98-1 3-acetyl-5-phenyl-isoxazole 
• 858489-69-7 3-(methoxymethyl)-5-phenylisoxazole 
• 90770-96-0 5-phenyl-isoxazole-3-carbaldehyde oxime 
• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 
• 107487-07-0 (E)-5-phenyl-3-(2-phenylethenyl)-2-isoxazoline 
• 583-05-1 1-phenylpentane-1,4-dione 
• 25741-97-3 3-amino-5-methylisoxazole 
• 124-38-9 carbon dioxide 
• 14442-24-1 5-phenylisoxazole-3-carbonitrile 
• 14337-43-0 ethyl 2-chloro-2-(hydroxyimino)acetate 
• 88330-79-4 2-hydroxy-4-oxo-4-phenylbut-2-enoic acid ethyl ester 
• 98-86-2 acetophenone 
• 20577-73-5 methyl 4-phenyl-2,4-dioxobutanoate 
• 51677-09-9 methyl 5-phenylisoxazole-3-carboxylate 

Downstream Products

• 20413-05-2 2-benzoyl-3-phenylacrylonitrile 
• 5356-71-8 1,3-diphenyl-1H-pyrazol-5-amine 
• 13599-22-9 1,5-diphenylpyrazole-3-carboxylic acid 
• 7063-98-1 3-acetyl-5-phenyl-isoxazole 
• 34671-15-3 3-benzoyl-5-methylisoxazole 
• 23088-52-0 5-phenylisoxazole-3-carboxamide 
• 614-16-4 Benzoylacetonitrile 
• 5071-61-4 5-phenyl-1H-pyrazole-3-carboxylic acid 
• 20413-07-4 2-benzoyl-3-(4-(dimethylamino)phenyl)acrylonitrile 
• 4852-81-7 2-benzoyl-3H-benzo[f]chromen-3-one 
• 1619-37-0 (5-phenylisoxazol-3-yl)methanol 
• 666859-30-9 N-[4-BROMO-2-(5-OXO-4, 5-DIHYDRO-1, 2,4-oxadiazol-3-yl) PHENYL]-5-PHENYLISOXAZOLE-3-CARBOXAMIDE 
• 1086562-36-8 2-[3-methoxy-2-[(5-phenylisoxazole-3-carbonyl)-amino]-phenyl]-benzoxazole-4-carboxylic acid methyl ester 
• 1314023-95-4 N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-5-phenyl-isoxazole-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and in Vitro Cytotoxic Activity of Novel Triazole-Isoxazole Derivatives

New derivatives of triazole-isoxazole were synthesized through a four-step reaction starting from various ethyl 4-aryl-2,4-dioxobutanoate derivatives. Finally, all compounds were examined by MTT assays for cytotoxic activity in two human breast cancer cell lines (MCF-7 and T-47D).

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Mechanochemistry Enabled Construction of Isoxazole Skeleton via CuO Nanoparticles Catalyzed Intermolecular Dehydrohalogenative Annulation

A dehydrohalogenative approach for isoxazole annulation by partnering β-vinyl halides and α-nitrocarbonyls under mechanochemical setting was accomplished. This chemistry is operative under the cooperative catalysis of cupric oxide nanoparticles (50 nm) a

Novel N-benzylpiperidine derivatives of 5-arylisoxazole-3-carboxamides as anti-Alzheimer's agents

The complex pathophysiology of Alzheimer's disease (AD) has prompted researchers to develop multitarget-directed molecules to find an effective therapy against the disease. In this context, a novel series of N-(1-benzylpiperidin-4-yl)-5-arylisoxazole-3-ca

Design and synthesis of novel 5-arylisoxazole-1,3,4-thiadiazole hybrids as α-glucosidase inhibitors

Background: α-Glucosidase inhibitors have occupied a significant position in the treatment of type 2 diabetes. In this respect, the development of novel and efficient non-sugar-based inhibitors is in high demand. Objective: Design and synthesis of new 5-arylisoxazole-1,3,4-thiadiazole hybrids possessing α-glucosidase inhibitory activity were developed. Methods: Different derivatives were synthesized by the reaction of various 5-arylisoxazole-3-carboxylic acids and ethyl 2-((5-amino-1,3,4-thiadiazol-2-yl)thio)acetate. Finally, they were evalu-ated for their α-glucosidase inhibitory activity. Results: It was found that ethyl 2-((5-(5-(2-chlorophenyl)isoxazole-3-carboxamido)-1,3,4-thiadiazol-2-yl)thio)acetate (5j) was the most potent compound (IC50 = 180.1 μM) compared with acarbose as the reference drug (IC50 = 750.0 μM). Also, the kinetic study of 5j revealed a competitive inhibition and docking study results indicated desired interactions of that compound with amino acid residues located close to the active site of α-glucosidase. Conclusion: Good α-glucosidase inhibitory activity obtained by the title compounds introduced them as an efficient scaffold, which merits to be considered in anti-diabetic drug discovery developments.

Discovery of Membrane-Bound Pyrophosphatase Inhibitors Derived from an Isoxazole Fragment

Membrane-bound pyrophosphatases (mPPases) regulate energy homeostasis in pathogenic protozoan parasites and lack human homologues, which makes them promising targets in e.g. malaria. Yet only few nonphosphorus inhibitors have been reported so far. Here, w

Design and Synthesis of Novel Arylisoxazole-Chromenone Carboxamides: Investigation of Biological Activities Associated with Alzheimer's Disease

A novel series of hybrid arylisoxazole-chromenone carboxamides were designed, synthesized, and evaluated for their cholinesterase (ChE) inhibitory activity based on the modified Ellman's method. Among synthesized compounds, 5-(3-nitrophenyl)-N-{4-[(2-oxo-

Discovery of 2-phenylthiazole-4-carboxylic acid, a novel and potent scaffold as xanthine oxidase inhibitors

The xanthine oxidase (XO) plays an important role in producing uric acid, and therefore XO inhibitors are considered as one of the promising therapies for hyperuricemia and gout. We have previously reported a series of XO inhibitors with pyrazole scaffold to extend the chemical space of current XO inhibitors. Herein, we describe further structural optimization to explore the optimal heterocycle by replacing the thiazole ring of Febuxostat with 5 heterocycle scaffolds unexplored in this field. All of these efforts resulted in the identification of compound 8, a potent XO inhibitor (IC50 = 48.6 nM) with novel 2-phenylthiazole-4-carboxylic acid scaffold. Moreover, lead compound 8 exhibited hypouricemic effect in potassium oxonate-hypoxanthine-induced hyperuricemic mice. These results promote the understanding of ligand-receptor interaction and might help to design more promising XO inhibitors.

Design and Synthesis of Selective Acetylcholinesterase Inhibitors: Arylisoxazole-Phenylpiperazine Derivatives

In this work, a novel series of arylisoxazole-phenylpiperazines were designed, synthesized, and evaluated toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Our results revealed that [5-(2-chlorophenyl)-1,2-oxazol-3-yl](4-phenylpiperazin

FIVE-MEMBERED HETEROCYCLIC AMIDES WNT PATHWAY INHIBITOR

The present invention discloses a five-membered heterocyclic amide WNT pathway inhibitor, which belongs to a compound that regulates the activity of a Wnt signaling pathway, and provides a method for preparing such a compound, and the use of such a compound in preparing a medicament that antagonizes the Wnt signaling pathway. The five-membered heterocyclic amide WNT pathway inhibitor provided by the invention has a remarkable anti-tumor activity based on a target-based rational drug design of, and can be used for the development of a new generation of Wnt pathway inhibitors, and has a great clinical application value and considerable market potential.