7063-99-2

Usage

Uses

Used in Organic Synthesis:
ETHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, facilitating the formation of new molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ETHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE is utilized as a building block for the development of biologically active compounds. Its incorporation into drug molecules can contribute to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in Medicinal Chemistry Research:
ETHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE is employed in medicinal chemistry research to explore its potential pharmacological properties. Studies have indicated that it possesses anticonvulsant and sedative effects, which could be harnessed in the development of new treatments for neurological disorders and conditions requiring sedation.
Used in Drug Development:
As a compound with demonstrated biological activity, ETHYL 5-PHENYL-3-ISOXAZOLECARBOXYLATE is used in drug development to create novel pharmaceuticals. Its unique chemical structure and pharmacological properties make it a valuable component in the design and synthesis of new drugs with potential therapeutic benefits.

InChI:InChI=1/C12H11NO3/c1-2-15-12(14)10-8-11(16-13-10)9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 52313-46-9 ethyl 2-acetyl-4-oxo-4-phenylbutanoate 
• 29113-48-2 ethyl 2-benzoyl-4-oxo-4-phenylbutanoate 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 7064-04-2 ethyl 5-phenyl-2-isoxazoline-3-carboxylate 
• 1199-95-7 1-(trimethylstannyl)-2-phenylethyne 
• 14337-43-0 ethyl 2-chloro-2-(hydroxyimino)acetate 
• 51983-62-1 carbethoxyformonitrile oxide 
• 626-35-7 nitroacetic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 88330-79-4 ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate 
• 15121-89-8 ethyl 3-benzoyl acrylate 
• 946-38-3 ethyl 2-phenylcyclopropylcarboxylate 
• 1221821-70-0 ethyl 5-hydroxy-5-phenyl-4,5-dihydro-3-isoxazolecarboxylate 

Downstream Products

• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 
• 159670-70-9 ethyl 5-(4-nitrophenyl)isoxazole-3-carboxylate 
• 78189-50-1 5-phenylisoxazole-3-carboxylic acid chloride 
• 90946-22-8 5-phenylisoxazole-3-carboxylic acid hydrazide 
• 76973-04-1 1-(5-Phenyl-isoxazol-3-yl)-pentan-1-one 
• 76973-06-3 1-(5-Phenyl-isoxazol-3-yl)-pentan-1-ol 
• 76973-13-2 5-(5-Phenyl-isoxazol-3-yl)-nonan-5-ol 
• 7063-98-1 3-acetyl-5-phenyl-isoxazole 
• 27409-56-9 3-(1-Hydroxy-1-methylethyl)-5-phenylisoxazole 
• 76973-03-0 1-(5-Phenyl-isoxazol-3-yl)-propan-1-one 
• 76973-12-1 3-(5-Phenyl-isoxazol-3-yl)-pentan-3-ol 
• 145440-89-7 5-Phenyl-isoxazole-3-carboxylic acid (2,6-dimethyl-phenyl)-amide 
• 1619-37-0 (5-phenylisoxazol-3-yl)methanol 
• 866641-27-2 ethyl (5-phenyl-1,2-oxazol-3-yl)methyl methanesulfonate 

Relevant academic research and scientific papers

Enantioselective Aza-Friedel-Crafts Reaction of Heteroarenes with in situ Generated Isoxazolium Ions via Chiral Phosphoric Acid Catalysis

An asymmetric organocatalytic aza-Friedel-Crafts reaction was developed to give the enantioenriched Δ4-isoxazoline scaffold bearing a quaternary-substituted stereogenic centre in good-to-excellent yields and enantioselectivity (50–99%, 55–>99% ee). This protocol involves the in situ generated isoxazolium ions in the presence of a chiral phosphoric acid followed by the heteroarene addition through asymmetric counteranion-directed catalysis. (Figure presented.).

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.

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

Synthesis, in vitro anticancer activity and in silico studies of certain isoxazole-based carboxamides, ureates, and hydrazones as potential inhibitors of VEGFR2

The ensuing research presents the results of in vitro anticancer activity of novel 28 compounds of isoxazole–based carboxamides 3(a-d); ureates 4(a-g), 5, 6, 7a,b, 8; and hydrazones 9(a-f), 10(a-d), 11a,b as potential inhibitors of VEGFR2. The carboxamide

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.

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

Synthesis of isoxazoles via cyclization of β-fluoro enones with sodium azide

A practical method for the synthesis of 3,5-disubstituted isoxazoles via cyclization of β-fluoro enones with sodium azide was disclosed. Density functional theory (DFT) calculation indicated that both (1) the azirine formation followed by intramolecular rearrangement and (2) direct enolate O-attack via 5-exo-trig cyclization of vinyl azide were possible for the isoxazole formation.

Discovery of heterocyclic carbohydrazide derivatives as novel selective fatty acid amide hydrolase inhibitors: design, synthesis and anti-neuroinflammatory evaluation

Fatty acid amide hydrolase (FAAH) is a promising target for the development of drugs to treat pain, inflammation, and other central nervous system disorders. Herein, a series of novel heterocyclic carbohydrazide derivatives were firstly designed by the classic scaffold-hopping strategy. Then, multi-steps synthesis and human FAAH enzyme inhibiting activity assays were conducted. Among them, compound 26 showed strong inhibition against human FAAH with IC50 of 2.8 μM. Corresponding docking studies revealed that the acyl hydrazide group of compound 26 well-occupied the acyl-chain binding pocket. It also exhibited high selectivity towards FAAH when comparing with CES2 and MAGL. Additionally, compound 26 effectively suppressed the LPS-induced neuroinflammation of microglial cells (BV2) via the reduction of interleukin-1β and tumor necrosis factor-α. Our results provided significative lead compounds for the further discovery of novel selective and safe FAAH inhibitors with potent anti-neuroinflammation activity.

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 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