79388-04-8

Basic information

• Product Name: 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile
• CAS NO: 79388-04-8
• Molecular Formula: C₁₃H₉N₅O
• Molecular Weight: 251.2435
• Mol File: 79388-04-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 375.8°C at 760 mmHg
• Flash Point: 181.1°C
• Density: 1.47g/cm³
• Vapor Pressure: 7.57E-06mmHg at 25°C
• Refractive Index: 1.715
• CAS DataBase Reference: 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile(79388-04-8)
• EPA Substance Registry System: 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile(79388-04-8)

Safety Data

• Hazardous Substances Data: 79388-04-8(Hazardous Substances Data)

Usage

Description

1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile is a complex chemical compound that belongs to the class of dihydropyridine compounds. It features two amino groups, a carbonyl group, a phenyl group, and two cyano groups, making it a versatile building block in organic synthesis. 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile holds significance in pharmaceutical and organic chemistry due to its potential applications in the synthesis of pharmaceutical drugs, development of new materials, and involvement in various organic reactions.

Uses

Used in Pharmaceutical Industry:
1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile is used as a key intermediate in the synthesis of pharmaceutical drugs for its potential to contribute to the development of new medications.
Used in Organic Chemistry Research:
In the field of organic chemistry, 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile serves as a valuable component in the exploration of new materials and reactions, furthering scientific understanding and innovation.
Used in Material Science:
1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile is also utilized in material science for the development of new materials, capitalizing on its unique structural attributes and functional groups to create novel substances with potential applications in various industries.

Upstream product

• 140-87-4 Cyanoacetohydrazide 
• 2700-22-3 Benzylidenemalononitrile 
• 4974-44-1 N'-benzylidenecyanoacetohydrazide 
• 109-77-3 malononitrile 
• 100-52-7 benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 124443-23-8 2-methyl-5-oxo-7-phenyl-3,5-dihydro-<1,2,4>triazolo<1,5-a>pyridine-6,8-dicarbonitrile 
• 129995-67-1 6-acetamido-1-diacetylamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile 
• 67720-42-7 6-amino-1,2-dihydro-2-oxo-4-phenylpyridine-3,5-dicarbonitrile 
• 1038081-85-4 1-amino-6-(triphenylphosphoranylideneamino)-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrileiminophosphorane 
• 1038081-88-7 5-oxo-7-phenyl-2-thiol-3,5-dihydro[1,2,4]triazolo[1,5-a]pyridine-6,8-dicarbonitrile 
• 1316852-75-1 (Z)-7-isocyano-2-(4-methylbenzylidene)-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-76-2 (Z)-7-isocyano-2-(4-isopropylbenzylidene)-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-77-3 (Z)-2-(4-(tert-butyl)benzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-68-2 (Z)-2-benzylidene-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-69-3 (Z)-2-(4-chlorobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-70-6 (Z)-2-(4-nitrobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-71-7 (Z)-7-isocyano-2-(4-methoxybenzylidene)-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-72-8 (Z)-2-(4-dimethylaminobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 
• 1316852-73-9 (Z)-2-(4-bromobenzylidene)-7-isocyano-3,6-dioxo-8-phenyl-3,6-dihydro-2H-thiazolo[3',2':2,3][1,2,4]triazolo[1,5-a]pyridine-9-carbonitrile 

Relevant articles and documents

A comparative screening of the catalytic activity of nanocrystalline MIIZr4(PO4)6 ceramics in the one-pot synthesis of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile derivatives

A four-component reaction of hydrazine hydrate, ethyl cyanoacetate, malononitrile, and aromatic aldehydes was achieved in the presence of nanocrystalline MIIZr4(PO4)6 ceramics (MII: Mn, Fe, Co, Ni, Cu, Zn, Cd) as heterogeneous catalysts to produce N-amino-2-pyridones. The reactions were performed in the presence of different catalysts, and it is observed that CdZr4(PO4)6 nanocrystallines are the best catalysts among those examined. Atom economy, excellent yields in short times, high catalytic activity, recycling of catalyst, and environmental benignity are some of the important features of this protocol.

An efficient method for the synthesis of N-amino-2-pyridones using reusable catalyst ZnO nanoparticles

A concise and highly efficient protocol for the synthesis of N.amino-2-pyridones has been developed by a four-component coupling of hydrazine hydrate, ethyl cyanoacetate, malononitrile and aromatic aldehydes in the presence of ZnO nanoparticles under mild conditions. The key advantages of this process are using an inexpensive and reusable catalyst, easy work.up and excellent yields.

Triazole-Pyridine Dicarbonitrile Targets Phosphodiesterase 4 to Induce Cytotoxicity in Lung Carcinoma Cells

Phosphodiesterase 4 (PDE4) is a key enzyme involved in the hydrolysis of cyclic adenosine monophosphate (cAMP) and widely expressed in several types of cancers. The inhibition of PDE4 results in an increased concentration of intracellular cAMP levels that imparts the anti-inflammatory response in the target cells. In the present report, two series of triazolo-pyridine dicarbonitriles and substituted dihydropyridine dicarbonitriles were synthesized using green protocol (TBAB in refluxed water). We next evaluated the title compounds for their cytotoxicity towards lung cancer (A549) cells and identified 7′-[4-(methylsulfonyl)phenyl]-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5h) and 7′-(1-methyl-1H-imidazol-2-yl)-5′-oxo-1′,5′-dihydrospiro[cyclohexane-1,2′-[1,2,4]triazolo[1,5-a]pyridine]-6′,8′-dicarbonitrile (5j) as lead analogs with the IC50 values of 15.2 and 24.1 μm, respectively. Furthermore, all the new compounds were tested for PDE4 inhibitory activity and 5j showed relatively good inhibitory activity towards PDE4 with inhibition of 50.9 % at 10 μm. In silico analysis demonstrated the favorable interaction of the title compounds with the target enzyme. Taken together, the present study introduces a new scaffold for the development of novel PDE4 inhibitors to fight against inflammatory diseases.

Convenient Synthesis of New Boric Acid Catalyzed 1,2,4-Triazolopyridinone Derivatives and an Investigation of their Optical Properties

Syntheses of fused heterobicyclic systems containing 1,2,4-triazolopyridinone moieties were accomplished by heterocyclization of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitriles and ninhydrin in ethanol and in the presence of boric acid as a catalyst in 30?min at room temperature. All compounds have been screened for their photophysical properties. Results showed that all compounds exhibit near infrared emissions at 876?nm.