78189-50-1

Usage

Uses

Used in Pharmaceutical Industry:
5-Phenylisoxazole-3-carbonyl chloride is used as a key intermediate for the synthesis of various pharmaceuticals. Its ability to introduce the isoxazole-3-carbonyl group into organic molecules makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 5-Phenylisoxazole-3-carbonyl chloride is used as a key intermediate in the synthesis of various agrochemicals. Its versatility in organic synthesis allows for the creation of compounds with potential applications in pest control and crop protection.
Used in Organic Synthesis:
5-Phenylisoxazole-3-carbonyl chloride is used as a reactive acylating agent in organic synthesis. Its ability to introduce the isoxazole-3-carbonyl group into organic molecules makes it a valuable tool for the development of new chemical compounds with various applications.
Used in Heterocyclic Compound Preparation:
As a versatile building block, 5-Phenylisoxazole-3-carbonyl chloride is used in the preparation of heterocyclic compounds. These compounds have a wide range of applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Production of Biologically Active Compounds:
5-Phenylisoxazole-3-carbonyl chloride is used as a key component in the production of a wide range of biologically active compounds. Its ability to be incorporated into various molecular structures allows for the development of new compounds with potential applications in medicine, agriculture, and other industries.

InChI:InChI=1/C10H6ClNO2/c11-10(13)8-6-9(14-12-8)7-4-2-1-3-5-7/h1-6H

Upstream product

• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 
• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 
• 6296-54-4 ethyl 2,4-dioxo-4-phenylbutyrate 
• 107487-07-0 (E)-5-phenyl-3-(2-phenylethenyl)-2-isoxazoline 
• 6502-37-0 (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one oxime 
• 14442-24-1 5-phenylisoxazole-3-carbonitrile 
• 90770-96-0 3-hydroxyiminomethyl-5-phenylisoxazole 

Downstream Products

• 1025771-17-8 N-(2-chloro-5-((((1R)-1-phenylethyl)amino)methyl)-phenyl)-5-phenyl-3-isoxazolecarboxamide 
• 1225136-26-4 C₂₄H₂₅N₄O₆P 
• 1350722-69-8 5-(2,4-dihydroxy-5-isopropylphenyl)-4-[(5-phenylisoxazole-3-carbonyl)amino]isoxazole-3-carboxylic acid ethylamide 
• 1363770-41-5 5-formyl-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-44-8 2-ethoxy-4-formylphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-56-2 (E)-4-(biphenyl-4-yliminomethyl)phenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-58-4 (E)-4-(2-hydroxyphenyliminomethyl)phenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-60-8 (E)-4-(biphenyl-4-yliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-62-0 (E)-4-(4-bromophenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-65-3 (E)-4-(2-hydroxyphenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-67-5 (E)-5-(biphenyl-4-yliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-69-7 (E)-5-(4-bromophenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-71-1 (E)-5-(2-hydroxyphenyliminomethyl)-2-methoxyphenyl 5-phenylisoxazole-3-carboxylate 
• 1363770-75-5 (E)-2-(biphenyl-4-yliminomethyl)-6-methoxyphenyl 5-phenylisoxazole-3-carboxylate 

Relevant academic research and scientific papers

Synthesis of 5-azolyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 5-azolyl-1,3,4-thiadiazol-2-amines based on derivatives of 5-arylisoxazole-3-carboxylic and 4,5-dichloroisothiazole-3-carboxylic acids

[Figure not available: see fulltext.] 2-Mercapto-1,3,4-triazoles and 2-amino-1,3,4-thiadiazoles were synthesized by successive transformations of 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carboxylic acids and their derivatives. The amino group of 5-(

Inhibitors of histone deacetylase 6 based on a novel 3-hydroxy-isoxazole zinc binding group

Histone deacetylase 6 (HDAC6) is an established drug target for cancer treatment. Inhibitors of HDAC6 based on a hydroxamic acid zinc binding group (ZBG) are often associated with undesirable side effects. Herein, we describe the identification of HDAC6 inhibitors based on a completely new 3-hydroxy-isoxazole ZBG. A series of derivatives decorated with different aromatic or heteroaromatic linkers, and various cap groups were synthesised and biologically tested. In vitro tests demonstrated that some compounds are able to inhibit HDAC6 with good potency, the best candidate reaching an IC50 of 700 nM. Such good potency obtained with a completely new ZBG make these compounds particularly attractive. The effect of the most active inhibitors on the acetylation levels of histone H3 and α- tubulin and their anti-proliferative activity of DU145 cells were also investigated. Docking studies were performed to evaluate the binding mode of these new derivatives and discuss structure-activity relationships.

Iron(iii)-catalyzed selective N-O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from: N -vinyl-α,β-unsaturated ketonitrones

An iron(iii)-catalyst controlled cyclization and selective N-O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(ii) acetate in combination with the prepared bidentate N-ligand was used.

The synthesis of isoxazolyl- and isothiazolylcarbamides exhibiting antitumor activity

Accessible 5-phenyl(p-tolyl)isoxazol-3-carboxylic, 4,5-dichlorothiazol-3-carboxylic and 5-(benzylsulfanyl)-4-chlorothiazol-3-carboxylic acids were converted via a series of cascade transformations into the corresponding (1,2-azolyl)-3-carbonyl azides whose reaction with slightly basic aryl(heteryl)amines led to generation of 1-(1,2-azolyl)-3-aryl(heteryl)carbamides. To obtain isoxazolyl(isothiazolyl)carbamides containing the residues of highly basic amines, (1,2-azolyl)-3-carbonyl azides were preliminary transformed into aryl (1,2-azol-3-yl)carbamates by the action of phenol or 4-fluorophenol. Carbamates then were introduced into reaction with aliphatic or heterocyclic amines. Some of the obtained compounds and their precursors show high antitumor activity and are capable to increase the effect of cytostatic drugs applied in the medical practice.

Synthesis of functionally substituted isoxazole and isothiazole derivatives

Acylation of benzene and toluene with 5-phenyl- and 5-(p-tolyl)isoxazole-3- carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH 3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.

Mononuclear heterocyclic rearrangement of 5-arylisoxazole-3-hydroxamic acids into 3,4-substituted 1,2,5-oxadiazoles

By a series of successive transformations, 5-arylisoxazole-3-carboxylic acids (aryl=phenyl, p-tolyl, 2,5-dimethylphenyl) have been converted into 5-arylisoxazole-3-hydroxamic acids, which undergo rearrangement by the action of aqueous KOH to form 3,4-substituted 1,2,5-oxadiazoles. The structure of one of them, 1-(2,5-dimethylphenyl)-2-(4-hydroxy-1,2,5-oxadiazol-3-yl)ethanone, has been confirmed by single crystal X-ray analysis. Georg Thieme Verlag Stuttgart New York.

Discovery, design and synthesis of a selective S1P3 receptor allosteric agonist

Potent and selective S1P3 receptor (S1P3-R) agonists may represent important proof-of-principle tools used to clarify the receptor biological function and assess the therapeutic potential of the S1P 3-R in cardiovascular, inflammatory and pulmonary diseases. N,N-Dicyclohexyl-5-propylisoxazole-3-carboxamide was identified by a high-throughput screening of MLSMR library as a promising S1P3-R agonist. Rational chemical modifications of the hit allowed the identification of N,N-dicyclohexyl-5-cyclopropylisoxazole-3-carboxamide, a S1P3-R agonist endowed with submicromolar activity and exquisite selectivity over the remaining S1P1,2,4,5-R family members. A combination of ligand competition, site-directed mutagenesis and molecular modeling studies showed that the N,N-dicyclohexyl-5-cyclopropylisoxazole-3-carboxamide is an allosteric agonist and binds to the S1P3-R in a manner that does not disrupt the S1P3-R-S1P binding. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the molecular basis of the receptor function, and provides the bases for further rational design of more potent and drug-like S1P3-R allosteric agonists.

Synthesis of hydroxybenzaldehyde derivatives containing an isoxazole heteroring

5-Phenyl(p-tolyl)isoxazole-3-carboxylic acids were synthesized starting from 3-hydroxyiminomethyl-5-phenyl(p-tolyl)isoxazoles, and their reactions with p-hydroxybenzaldehyde, vanillin, isovanillin, o-vanillin, and ethyl vanillin gave the corresponding esters. The latter were brought into condensation with aromatic amines to obtain Schiff bases which were reduced to amines. Pleiades Publishing, Ltd., 2012.

Novel tetrahydropyrido[1,2-a]isoindolone derivatives (valmerins): Potent cyclin-dependent kinase/glycogen synthase kinase 3 inhibitors with antiproliferative activities and antitumor effects in human tumor xenografts

The development of CDK and GSK3 inhibitors has been regarded as a potential therapeutic approach, and a substantial number of diverse structures have been reported to inhibit CDKs and GSK-3β in recent years. Only a few molecules have gone through or are currently undergoing clinical trials as CDK and GSK inhibitors. In this paper, we prepared valmerins, a new family containing the tetrahydropyrido[1,2-a]isoindone core. The fused heterocycle was prepared with a straightforward synthesis that was functionalized by a (het)arylurea. Twelve valmerins inhibited the CDK5 and GSK3 with an IC50 100 nM. A semiquantitative kinase scoring was realized, and a cellular screening was done. At the end of our study, we investigated the in vivo potency of one valmerin. Mice exhibited good tolerance to our lead, which proved its efficacy and clearly blocked tumor growth. Valmerins appear also as good candidates for further development as anticancer agents.

Preparation of novel antibacterial agents. Replacement of the central aromatic ring with heterocycles

Discovery of novel antibacterial agents is a significant challenge. We have recently reported on our discovery of novel antibacterial agents in which we have rapidly optimized potency utilizing a parallel chemistry approach. These advanced leads suffer from high affinity for human serum albumin (HSA). In an effort to decrease the affinity for HSA we have prepared a series of heterocyclic analogs, which retained antibacterial activity and demonstrated reduced affinity for HSA.