100675-76-1

Usage

Chemical Class

Isoxazole derivative

Function

Potent and non-selective inhibitor of cyclic nucleotide phosphodiesterases (PDEs)

Enzyme Inhibition

Inhibits PDEs involved in regulating intracellular levels of cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP)

Scientific Research

Extensively used as a tool to investigate the role of PDEs in various physiological and pathological processes

Applications

Studied for potential therapeutic applications in treating conditions related to cAMP and cGMP signaling dysregulation

Potential Therapeutic Uses

Respiratory diseases, cardiovascular disorders, neurodegenerative diseases

Research Tools

Used in studies related to cell signaling, neurotransmission, and smooth muscle relaxation.

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 140-29-4 phenylacetonitrile 
• 51073-69-9 (2-amino-5-iodophenyl)(phenyl)methanone 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Downstream Products

• 51073-69-9 (2-amino-5-iodophenyl)(phenyl)methanone 
• 97423-34-2 8-Iodo-6-phenyl-1-(phenylmethyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine 
• 97423-32-0 N-(2-Benzoyl-4-iodo-phenyl)-2-bromo-acetamide 
• 97423-33-1 1,3-dihydro-7-iodo-5-phenyl-2H-1,4-benzodiazepine-2-thione 
• 60114-64-9 7-iodo-5-phenyl-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one 

Relevant academic research and scientific papers

Synthesis of 3-phenylbenzo[c]isoxazoles by thermocyclization of 2-azidobenzophenones

3-Phenylbenzo[c]isoxazoles were synthesized by non-catalytic thermolysis of 2-azidobenzophenones in dry xylene with quantitative yields. The trace content of water in solvents reduces the yields of the reaction products. 2-Azidobenzoic acid esters are sta

Nucleophilic replacement of hydrogen in para-substituted nitrobenzenes by phenylacetonitrile carbanion

The kinetic relations holding in nucleophilic replacement of hydrogen in para-substituted nitrobenzenes by phenylacetonitrile carbanion suggest a complex reaction mechanism involving two alternative pathways. The direction of the process is determined by the structure of intermediate σ-complex.

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone

An efficient approach to the synthesis of 2,1-benzisoxazoles through direct construction of the N-O bond by the chemoselective oxidation of 2-aminoacylbenzenes with Oxone is described. This alternative methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing Oxone as a green oxidant instead of hypervalent iodine compounds. Moreover, this new procedure simplifies the number of steps compared to the previously reported procedure by circumventing the use of 2-azido-substituted aryl ketones.

Nucleophilic substitution of hydrogen in activated nitroarenes by phenylacetonitrile carbanion

General relations holding in nucleophilic substitution of hydrogen in para-substituted nitroarenes by phenylacetonitrile carbanion were analyzed in terms of the Klopman reactivity indices. Requirements to the substrate structure were determined, which restrict the scope of application of this method to synthesis of 2,1-benzisoxazole derivatives.

Substituent Effect on the Reaction Rate of para-Substituted Nitrobenzenes with Phenylacetonitrile

The substituent effect on the reaction rate of para-substituted nitrobenzenes with the phenylacetonitrile was evaluated using the model of orbital interactions. The limiting step of the reaction was presumed to have associative character.

FUNCTIONALIZATION OF AROMATIC COMPOUNDS BY NUCLEOPHILIC SUBSTITUTION OF A HYDROGEN ATOM BY THE PHENYLACETONITRILE CARBANION

Aromatic nitro compounds containing a substituent at the para react with phenylacetonitrile in an alcohol solution of alkali with the formation of 2,1-benzisoxazoles.The CH3, NH2, OH, and certain other substituents prevent the reaction.In the reaction of benzonitrile and phthalonitrile with phenylacetonitrile in the sodium hydroxide-DMSO system substitution of a hydrogen atom at the ortho position to the nitrile group is observed; the products from substitution of a hydrogen atom were not obtained in the reaction of phenylacetonitrile with aromatic nitriles containing other substituents.

1-(2-Aminoethyl)-6-aryl-4H-triazolobenzodiazepines with Diuretic and Natriuretic Activity

A series of 1-(2-amino-1-phenylethyl)-6-phenyl-4H-triazolobenzodiazepines was prepared and evaluated for diuretic activity.These compounds have diuretic and natriuretic activity but no kaliuretic activity when evaluated by oral administration to the conscious rat.The structure requirements for this activity are discussed.In particular it was found that the 2-aminoethyl side chain at C-1 with hydrogen or methyl substituents on the amino group was required for diuretic acitvity.A substituent at C-8 was also required: soft substituents such asmethylthio and iodo at this position favored activity.Compounds with both phenyl and 2-pyridyl substituents at C-6 were active; substituents on the C-6 phenyl, however, reduced or eliminated the activity.Substituents other than phenyl at the 1-position of the 2-aminoethyl side chain were detrimental to the activity; phenyl substitution at this position was required for activity when the substituent at C-8 was chloro but not when it was bromo.