53557-94-1

Basic information

• Product Name: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-
• Synonyms: 3-methyl-4-nitro-5-trans-styryl-isoxazole;Isoxazole,3-methyl-4-nitro-5-(2-phenylethenyl);3-methyl-4-nitro-5-styryl-isoxazole;3-methyl-5-styryl-4-nitroisoxazol;(E)-3-methyl-4-nitro-5-styrylisoxazole
• CAS NO: 53557-94-1
• Molecular Formula: C12H10N2O3
• Molecular Weight: 230.223
• Mol File: 53557-94-1.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-(53557-94-1)
• EPA Substance Registry System: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-(53557-94-1)

Safety Data

• Hazardous Substances Data: 53557-94-1(Hazardous Substances Data)

Upstream product

• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 123-54-6 acetylacetone 
• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 100-52-7 benzaldehyde 
• 79510-57-9 3-<1-phenyl-2-(3-methyl-4-nitro-5-isoxazolyl)-ethyl>pentane-2,4-dione 

Downstream Products

• 79510-67-1 3,5-diphenyl-4-(3-methyl-4-nitro-5-isoxazolyl)-2-isoxazoline 
• 79510-57-9 3-<1-phenyl-2-(3-methyl-4-nitro-5-isoxazolyl)-ethyl>pentane-2,4-dione 
• 51978-95-1 5-(1,2-dibromo-2-phenylethyl)-3-methyl-4-nitroisoxazole 
• 58935-96-9 1-Nitro-propan-2-one oxime 
• 621-82-9 Cinnamic acid 
• 637-44-5 phenylpropyolic acid 
• 1205553-81-6 3-methyl-4-nitro-5-((2S,3R)-3-nitro-2-phenylbutyl)isoxazole 
• 1205553-66-7 (S)-3-methyl-4-nitro-5-(3-nitro-2-phenylpropyl)isoxazole 
• 1205553-71-4 (R)-3-methyl-4-nitro-5-(3-nitro-2-phenylpropyl)isoxazole 
• 1205553-80-5 (S)-3-methyl-5-(3-methyl-3-nitro-2-phenylbutyl)-4-nitroisoxazole 
• 1205553-83-8 3-methyl-4-nitro-5-((2S,3R)-3-nitro-2,4-diphenylbutyl)isoxazole 
• 1205553-88-3 3-methyl-4-nitro-5-((2S,3S)-3-nitro-2,4-diphenylbutyl)isoxazole 

Relevant articles and documents

Chiral 4 and 5 - disubstituted pyrrolidine -2 - ketone compound as well as preparation method and application thereof

The invention belongs to the technical field of organic synthesis, and particularly relates to chiral 4, 5 - disubstituted pyrrolidine -2 - ketone compounds as well as a preparation method and application thereof. The invention firstly uses nitro substituted alkyl (I) and trans α, β - unsaturated 3 - methyl -4 - nitroisoxazole (II) as raw materials, and the asymmetric Michael addition reaction of chiral superbase catalysis I and II is a key step and is hydrolyzed. Esterification and reduction closes the ring, synthesizing a chiral 3, 4 - disubstituted pyrrolidine -2 - ketone compound, including optically pure fenoxone. The asymmetric Michael addition reaction of chiral superbase catalyst for catalyzing 2 -substituted nitroethane (I) and trans α, β -unsaturated 3 - methyl -4 - nitroisoxazole (II) is used for preparing chiral 4 and 5 -disubstituted pyrroli -2 - ketone, and a strapdown is provided for synthesizing chiral 4 and 5 - disubstituted pyrrolidine -2 - ketone skeleton.

Structure–activity relationships of GPX4 inhibitor warheads

Direct inhibition of GPX4 requires covalent modification of the active-site selenocysteine. While phenotypic screening has revealed that activated alkyl chlorides and masked nitrile oxides can inhibit GPX4 covalently, a systematic assessment of potential electrophilic warheads with the capacity to inhibit cellular GPX4 has been lacking. Here, we survey more than 25 electrophilic warheads across several distinct GPX4-targeting scaffolds. We find that electrophiles with attenuated reactivity compared to chloroacetamides are unable to inhibit GPX4 despite the expected nucleophilicity of the selenocysteine residue. However, highly reactive propiolamides we uncover in this study can substitute for chloroacetamide and nitroisoxazole warheads in GPX4 inhibitors. Our observations suggest that electrophile masking strategies, including those we describe for propiolamide- and nitrile-oxide-based warheads, may be promising for the development of improved covalent GPX4 inhibitors.

Styrylisoxazole-based fluorescent probes for the detection of hydrogen sulfide

Styrylisoxazoles bearing a nitro group linked to bulky aromatic rings have been synthesized and examined for their absorption and emission studies in organic solvents and water. The molecules showed emission in the visible region with significant solvatochromic emission shifts influenced by the extended conjugation of aromatic rings and intramolecular charge transfer. These absorption and emission changes were used for the efficient and sensitive detection of trace concentrations of hydrogen sulfide (H2S) through the reduction of the nitro group to the amine group in the presence of aqueous sodium sulfide. The experimental results indicated that the probes exhibit an excellent emission response with large shifts in the emission and sensitivity with a micromolar detection limit.