20357-59-9

Usage

InChI:InChI=1/C13H11NO2/c15-13-9-5-4-6-11(13)10-14(16)12-7-2-1-3-8-12/h1-10,16H/b11-10+

Upstream product

• 90-02-8 salicylaldehyde 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 

Downstream Products

• 3526-45-2 2-((phenylamino)methyl)phenol 
• 779-84-0 N-phenylsalicylaldimine 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 90-02-8 salicylaldehyde 
• 17082-12-1 trans-azobenzene 
• 69-72-7 salicylic acid 
• 130088-43-6 1-hydroxy-2-(2'-hydroxyphenyl)benzimidazole-3-N-oxide 
• 1357560-66-7 C₁₉H₁₇NO₆ 
• 1357560-77-0 C₁₉H₁₇NO₆ 
• 495-48-7 azoxybenzene 
• 71-36-3 butan-1-ol 

Relevant academic research and scientific papers

Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives

In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR,1H NMR,13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.

Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines

An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.

Synthesis and evaluation of novel 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-diones for advanced glycation end product formation inhibitory activity

The synthesis of some biologically interesting pyrrolo-isoxazolidine derivatives was accomplished by the 1,3-dipolar cycloaddition reaction of substituted azomethine N-oxides 1 with substituted N-aryl maleimides 2 leading to the formation of new stereoisomeric 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives 3 in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay. All the synthesized compounds have been found to exhibit significant activity against AGE formation.

Synthesis and evaluation of novel 4-[(3H,3aH,6aH)-3-phenyl)-4,6-dioxo-2- phenyldihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic acid derivatives as potent acetylcholinesterase inhibitors and anti-amnestic agents

The present study was designed to synthesize and evaluate pyrrolo-isoxazole benzoic acid derivatives as potential acetylcholinesterase (AChE) inhibitors for the management of Alzheimer's disease. The synthesis of pyrrolo-isoxazole benzoic acid derivatives involved ring opening cyclization of p-aminobenzoic acid with maleic anhydride to yield maleanilic acid, which in turn afforded N-arylmaleimide via ring closed cyclization. Azomethine-N-oxides were obtained by condensation of N-arylhydroxylamine with differently substituted benzaldehydes followed by refluxing of N-arylmaleimide with differently substituted azomethine-N-oxides to pyrrolo-isoxazole benzoic acid derivatives as cis- and trans-stereoisomers. The synthesized compounds were evaluated in vitro for AChE inhibitory activity in rat brain homogenate with donepezil as standard AChE inhibitor. Thereafter, the most potent test compound was evaluated for in vitro butyrylcholinesterase inhibitory activity and in vivo memory evaluation in scopolamine (0.4 mg/kg)-induced amnesia in mice by employing Morris water maze test. All pyrrolo-isoxazole benzoic acid derivatives demonstrated potent AChE inhibitory activity. Most of compounds exhibited similar activity to donepezil and four of them (7h, 7i, 8i, and 8h, IC50 = 19.1 ± 1.9-17.5 ± 1.5 nM) displayed higher inhibitory activity as compared to donepezil (21.5 ± 3.2 nM) with compound 8ia (IC50 = 17.5 ± 1.5 nM) being the most active one. The test compound 8ia also ameliorated scopolamine-induced amnesia in mice in terms of restoration of time spent in target quadrant (TSTQ) and escape latency time (ELT). It may be concluded that pyrrolo-isoxazole benzoic acid derivatives may be employed as potential AChE inhibitors.

Synthesis and evaluation of hexahydropyrrolo[3,4-d]isoxazole-4,6-diones as anti-stress agents

A series of 2,3-diphenyl-5-(naphthalen-1-yl)-4H-2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives were synthesized via 1,3-dipolar cycloaddition of azomethine N-oxides with N-(α-naphthyl) maleimide. The pyrrolo-isoxazole derivatives were assigned cis- and trans- configurations (3-A and 3-B) with respect to proton C3-H on azomethinic carbon on the basis of their 1H NMR. The reaction proceeds through cis- endo addition rule indicating the predominance of cis isomer. The cis- and trans- isomers of a prototype compound 3a i.e., compound 3a-A and compound 3a-B were evaluated for anti-stress activity in immobilization-induced acute stress. Compound 3a-A (5 and 10 mg/kg) and compound 3a-B (10 mg/kg) attenuated immobilization stress-induced behavioral alterations in Swiss albino mice suggesting that pyrrolo-isoxazole may serve as lead molecule for the development of anti-stress agents.

Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to synthesis of a large variety of nitrones

Under mild microwave irradiation conditions and without any additional organic solvents, a large variety of nitrones were prepared in a weak Lewis base phosphinite task-specific ionic liquid (TSILOPPh2) in excellent yields. This catalytic TSIL was also re

Synthesis of neutral spin-delocalized electron acceptors for multifunctional materials

(Chemical Equation Presented) A new synthetic route to stable spin-delocalized radicals, annelated nitronyl nitroxides, has been developed on the basis of the condensation of benzofuroxan with aryl nitrones. The electronic structure of the resulting radic

A clean clay catalysed synthesis of α,N-diarylnitrones

The first clean and the facile clay catalysed synthesis of α,N-diarylnitrones in good yield is reported.

1H and 13C NMR Spectra of (Z)-N(o-Hydroxybenzylidene)-p-X-phenylamine N-Oxides and (Z)-N-(2-Hydroxy-1-naphthylmethylene)-p-X-phenylamine N-Oxides

Substituent effects on the 1H and 13C chemical shifts of (Z)-N-(o-hydroxybenzylidene)-p-X-phenylamine N-oxides and (Z)-N-(2-hydroxy-1-naphthylmethylene)-p-X-phenylamine N-oxides have been obtained.A combination of SFDOR and NOE methods was necessary for complete assignment of signals in the naphthalene series.Correlations have been found between the chemical shifts of various protons and carbons and Hammett ? parameters and Swain and Lupton F and R parameters.With both series of compounds a fixed conformation, due to intramolecular hydrogen bonding, is observed which affects the polarity of the nitrone group compared with that in α,N-diphenyl nitrone.Reduced through-resonance between aryl rings via the nitrone function was found.This may be attributed to the α-aryl ring and the nitrone group being held out of coplanarity by the hydrogen bond.

Method of treating inflammation

Relief of inflammation and associated pain and fever by the topical administration of α-phenyl-N-phenylnitrone and its derivatives.