96520-39-7

Usage

Uses

Used in Pharmaceutical Industry:
4-BUTYL-5-METHYL-3-ISOXAZOLOL is used as a synthetic intermediate for the development of various drugs. Its unique structure allows it to be a key component in the creation of pharmaceuticals that target a range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 4-BUTYL-5-METHYL-3-ISOXAZOLOL is utilized as a building block in the synthesis of pesticides. Its incorporation aids in the development of effective compounds designed to protect crops from pests and diseases.
Used in Organic Chemistry Research:
4-BUTYL-5-METHYL-3-ISOXAZOLOL is also used as a subject of study for its potential biological activities. Researchers are exploring its antifungal and antitumor properties, which could lead to new treatments and therapies in medicine.
Used in the Synthesis of Biologically Active Compounds:
Due to its heterocyclic nature, 4-BUTYL-5-METHYL-3-ISOXAZOLOL is employed in the synthesis of compounds with significant biological activity. This makes it a valuable asset in medicinal chemistry for the discovery of new pharmaceutical agents.

InChI:InChI=1/C8H13NO2/c1-3-4-5-7-6(2)11-9-8(7)10/h3-5H2,1-2H3,(H,9,10)

Upstream product

• 32798-42-8 methyl α-butylacetoacetate 
• 1540-29-0 ethyl 2-butylacetoacetate 

Downstream Products

• 143006-83-1 4-butyl-2,5-dimethylisoxazolin-3-one 
• 143006-81-9 4-butyl-3-methoxy-5-methylisoxazole 

Relevant academic research and scientific papers

Excitatory amino acid receptor ligands. Synthesis and biological activity of 3-isoxazolol amino acids structurally related to homoibotenic acid

The 3-isoxazolol amino acid (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4- yl)propionic acid (AMPA, 2) and the isomeric compound (RS)-2-amino-3-(3- hydroxy-4-methylisoxazol-5-yl)propionic acid (4-methylhomoibotenic acid, 4a) are potent agonists at the AMPA subtype of central excitatory amino acid receptors. Using 4a as a lead structure, the amino acids 4c-e, in which the 4-methyl group of 4a is replaced by substituents of different size and polarity, were synthesized. Attempts to synthesize 4- (bromomethyl)homoibotenic acid (4f), a potential receptor alkylating agent, were unsuccessful. 4-Butylhomoibotenic acid (4c) and 4-(2- hydroxyethyl)homoibotenic acid (4e) were equipotent as inhibitors of [3H]AMPA binding (IC50 = 2 μM) and showed similar excitatory activity in the rat cortical slice preparation. 4d did not show significant affinity for AMPA receptor sites, but turned out to be a weak N-methyl-D-aspartic acid (NMDA) receptor antagonist. However, like 4c,e, 4d did not significantly affect the binding of the competitive NMDA antagonist, [3H]CPP, or the noncompetitive NMDA antagonist, [3H]MK-801. None of the amino acids 4c-e showed detectable affinity for [3H]kainic acid binding sites. Like the parent compound 4a (IC50 = 0.18 μM), 4c (IC50 = 0.18 μM), 4e (IC50 = 0.14 μM), and in particular 4d (IC50 = 0.02 μM) were effective inhibitors of calcium chloride-dependent [3H]glutamic acid binding, whereas AMPA is inactive (IC50 > 100 μM) in this binding assay. Thus, 4d is an effective and highly selective inhibitor of calcium chloride-dependent [3H]glutamic acid binding and may be a useful tool for studies of the physiological relevance and pharmacological importance of this binding affinity.

Synthesis of 3-Hydroxyisoxazoles from β-Ketoesters and Hydroxylamine

An efficient synthesis of 3-hydroxyisoxazoles from β-ketoesters and hydroxylamine was investigated.The reaction of the sodium salts of β-ketoesters and hydroxylamine at a low temperature, followed by quenching with an excess of conc.HCl under heating gave predominantly 3-hydroxyisoxazoles involving 4-sulfenylated 3-hydroxyisoxazoles.Starting from the prepared 4-(2,4-dichlorobenzyl)-3-hydroxy-5-methylisoxazole, a potential herbicidal compound, 4-(2,4-dichlorobenzoyl)-3-hydroxy-5-methylisoxazole, was also synthesized in five steps.