28883-91-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-METHYLPHENYL)ISOXAZOL-5-AMINE is used as a building block for the synthesis of various biologically active molecules for the development of pharmaceutical drugs. Its unique structure and properties make it a valuable component in the creation of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
3-(4-METHYLPHENYL)ISOXAZOL-5-AMINE is used as a building block for the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the development of effective and targeted agrochemicals to protect crops and enhance agricultural productivity.
Used in Research Applications:
3-(4-METHYLPHENYL)ISOXAZOL-5-AMINE is used as a research compound to study its potential pharmacological properties, such as anti-inflammatory and antimicrobial activities. This research can lead to the discovery of new therapeutic agents and contribute to the advancement of medical and pharmaceutical sciences.
Used in Drug Discovery and Development:
3-(4-METHYLPHENYL)ISOXAZOL-5-AMINE is used as a starting material or intermediate in the synthesis of new drug candidates. Its unique chemical structure and properties make it a valuable component in the development of innovative and effective pharmaceuticals to treat various diseases and conditions.

InChI:InChI=1/C10H10N2O/c1-7-2-4-8(5-3-7)9-6-10(11)13-12-9/h2-6H,11H2,1H3

Upstream product

• 151-50-8 potassium cyanide 
• 71426-52-3 Syn-α-Brom-p-methyl-acetophenon oxim 
• 71707-42-1 2-chloro-3-(4-methylphenyl)prop-2-enenitrile 
• 7391-28-8 p-tolueneacetonitrile 

Downstream Products

• 7664-41-7 ammonia 
• 7803-49-8 hydroxylamine 
• 7391-28-8 p-tolueneacetonitrile 
• 949874-33-3 C₁₇H₁₆N₄O₃ 
• 1253696-34-2 3-(4-methylphenyl)isoxazolo[5,4-b]pyridine-5-carbaldehyde 
• 1620103-06-1 [5-amino-3-(4-methylphenyl)isoxazol-4-yl]thiocyanate 
• 28883-95-6 3-(p-tolyl)-2H-azirine-2-carboxamide 

Relevant academic research and scientific papers

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

Reactions of 5-Aminoisoxazoles with α-Diazocarbonyl Compounds: Wolff Rearrangement vs N-H Insertion

A highly chemoselective reaction between 5-aminoisoxazoles and α-diazocarbonyl compounds has been described. Both Wolff rearrangement and N-H insertion products can be obtained selectively by the judicious choice of reaction conditions. In the case of the

Hoveyda-Grubbs II Catalyst: A Useful Catalyst for One-Pot Visible-Light-Promoted Ring Contraction and Olefin Metathesis Reactions

A one-pot reaction to synthesize functionalized 2H-azirines through visible-light-mediated ring contraction and olefin metathesis of isoxazoles is described. Hoveyda-Grubbs II catalyst was found to function as a photocatalyst for these transformations, al

Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds

Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established a

The study of reactions of α-chlorocinnamonitriles with hydroxylamine

The E-isomers of α-chlorocinnamonitriles react with hydroxylamine to give a mixture of isomeric aminoisoxazoles, while the Z-isomers yield 3-aryl-2-chloroacrylamide oximes.

A modified procedure for the synthesis of 5-amino-3-arylisoxazoles and their reactions with tetrasulfur tetranitride antimony(V) chloride complex (S4N4·SbCl5): Novel synthesis of 3-aryl-1,2,5-thiadiazole-4-carboxamides

Dropwise addition of α-bromo ketoximes to a solution of KCN in MeOH at room temperature gave 5-amino-3-arylisoxazoles in moderate to good yields. Treatment of the isoxazoles prepared with tetrasulfur tetranitride antimony (V) chloride complex (S4N4·SbCl5) in toluene at 100°C afforded novel 3-aryl-1,2,5-thiadiazole-4-carboxamides.