680215-01-4

Basic information

• Product Name: 1,6-diamino-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
• Synonyms: 1,6-diamino-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
• CAS NO: 680215-01-4
• Molecular Weight: 311.3
• Mol File: 680215-01-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,6-diamino-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-diamino-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile(680215-01-4)
• EPA Substance Registry System: 1,6-diamino-4-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile(680215-01-4)

Safety Data

• Hazardous Substances Data: 680215-01-4(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 140-87-4 Cyanoacetohydrazide 
• 2972-80-7 3,4-dimethoxybenzylidenemalononitrile 
• 109-77-3 malononitrile 

Downstream Products

• 1184721-96-7 C₁₆H₁₁N₅O₃ 

Relevant articles and documents

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.

An efficient and ecofriendly synthesis of highly functionalized pyridones: Via a one-pot three-component reaction

A simple and convenient protocol has been developed for the synthesis of N-amino-3-cyano-2-pyridone derivatives by a one-pot reaction of cyanoacetohydrazide, activated nitrile substrates (malononitrile, ethyl cyanoacetate, cyanoacetamide) and aromatic ald