33282-16-5

Basic information

• Product Name: 5-(4-METHOXYPHENYL)ISOXAZOLE-3-CARBOXYL&
• Synonyms: 5-(4-METHOXYPHENYL)ISOXAZOLE-3-CARBOXYL&;5-(4-methoxyphenyl)isoxazole-3-carboxylic acid(SALTDATA: FREE);5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid 97%;5-(4-methoxyphenyl)-1,2-oxazole-3-carboxylic acid;5-(4-methoxyphenyl)-3-isoxazolecarboxylic acid
• CAS NO: 33282-16-5
• Molecular Formula: C₁₁H₉NO₄
• Molecular Weight: 219.195
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Isoxazoles
• Mol File: 33282-16-5.mol

Chemical Properties

• Melting Point: 181 °C (dec.)(lit.)
• Boiling Point: 461.1°C at 760 mmHg
• Flash Point: 232.7°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 2.67E-09mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-(4-METHOXYPHENYL)ISOXAZOLE-3-CARBOXYL&(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-METHOXYPHENYL)ISOXAZOLE-3-CARBOXYL&(33282-16-5)
• EPA Substance Registry System: 5-(4-METHOXYPHENYL)ISOXAZOLE-3-CARBOXYL&(33282-16-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 33282-16-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid is utilized as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be incorporated into drug molecules, potentially enhancing their therapeutic effects and pharmacological properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid serves as a valuable component for the design and development of new drugs. Its presence in molecular structures can contribute to the modulation of biological activities, making it a promising candidate for the treatment of various diseases and conditions.
Used in Drug Discovery:
5-(4-Methoxyphenyl)isoxazole-3-carboxylic acid is employed in drug discovery processes to identify and optimize potential drug candidates. Its unique chemical properties and structural features make it a versatile component in the creation of novel therapeutic agents with improved efficacy and selectivity.
Used in Chemical Research:
5-(4-METHOXYPHENYL)ISOXAZOLE-3-CARBOXYL& is also used in chemical research to explore its reactivity, stability, and potential interactions with other molecules. Understanding these properties can lead to the development of new synthetic routes and applications in various chemical and pharmaceutical processes.

InChI:InChI=1/C11H9NO4/c1-15-8-4-2-7(3-5-8)10-6-9(11(13)14)12-16-10/h2-6H,1H3,(H,13,14)

Upstream product

• 63913-14-4 2-hydroxy-4-oxo-4-(4-methoxyphenyl)but-2-enoic acid ethyl ester 
• 35322-20-4 ethyl 3-(4-methoxybenzoyl)pyruvate 
• 925006-96-8 ethyl 5-(4-methoxyphenyl)isoxazole-3-carboxylate 
• 943-88-4 4-(p-methoxyphenyl)-3-butene-2-one 
• 425609-97-8 methyl 5-(4-methoxyphenyl)isoxazole-3-carboxylate 
• 39757-31-8 methyl (4-methoxybenzoyl)pyruvate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 1416981-47-9 C₃₃H₃₀N₂O₁₀ 
• 33282-15-4 5-(4-hydroxyphenyl)isoxazole-3-carboxylic acid 
• 1391626-10-0 (3S,6S)-3,6-diisobutyl-4-(5-(4-methoxyphenyl)isoxazole-3-carbonyl)piperazin-2-one 

Relevant articles and documents

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-

Novel indole-isoxazole hybrids: Synthesis and in vitro anti-cholinesterase activity

Background: This work reports synthesis and in vitro cholinesterase inhibitory activity of novel indole-isoxazole hybrids. Method: The synthetic procedure was started from different ethyl 5-Arylisoxazole-3-carboxylate derivatives. Hydrolysis and reaction

Synthesis, biological evaluation and molecular modeling studies of psammaplin A and its analogs as potent histone deacetylases inhibitors and cytotoxic agents

In this study, a concise synthetic method of psammaplin A was achieved from 3-bromo-4-hydroxybenzaldahyde and hydantoin through a four-step synthesis via Knoevenagel condensation, hydrolysis, oximation and amidation in 37% overall yield. A collection of novel psammaplin A analogs focused on the variations of substituents at the benzene ring and modifications at the oxime moiety were synthesized. Among all the synthesized compounds, 5d and 5e showed better HDAC inhibition than psammaplin A and comparable cytotoxicity against four cancer cell lines (PC-3, MCF-7, A549 and HL-60). Molecular docking and dynamics simulation revealed that (i) hydrogen atom of the oxime group interacts with Asp99 of HDAC1 through a water bridged hydrogen bond and (ii) a hydroxyl group is optimal attached on the para-position of benzene, interacting with Glu203 at the entrance to the active site tunnel.

O-iodoxy benzoic acid–mediated synthesis of 3,5-diarylisoxazoles and isoxazole-3-carboxylic acids

A new, convenient, ecofriendly synthesis of 3,5-diarylisoxazoles is reported from a,b-unsaturated ketoximes. Similarly, a novel synthesis of isoxazole carboxylic acids is also reported. Both the methods use efficient, environmentally friendly, and nontoxic iodoxybenzoic acid (IBX) as an oxidative cyclizing reagent. Easy procedure, environmentally benign reaction conditions, and nontoxicity are advantages to the methodology.

Synthesis and anticancer activity of heteroaromatic linked 4β-amido podophyllotoxins as apoptotic inducing agents

A series of different heteroaromatic linked 4β-amidopodophyllotoxin conjugates (16a-i, 17a-i and 18a-d) were synthesized and evaluated for anticancer activity against five human cancer cell lines. Among the series, one of the compound 17g showed significant antiproliferative activity in A549 (lung cancer) cell line. Flow cytometric analysis showed that 17g arrested the cell cycle in the G2/M phase leading to caspase-3 dependent apoptotic cell death. Further, Hoechst 33258 staining and DNA fragmentation assay also suggests that 17g induces cell death by apoptosis.