79388-08-2

Upstream product

• 140-87-4 Cyanoacetohydrazide 
• 2700-23-4 4-Nitrobenzylidenemalononitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 105-56-6 ethyl 2-cyanoacetate 
• 109-77-3 malononitrile 

Downstream Products

• 79388-12-8 6-Amino-4-(4-nitro-phenyl)-2-oxo-1,2-dihydro-pyridine-3,5-dicarbonitrile 

Relevant academic research and scientific papers

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.

Dipyrido[1,2-b:3′,4′-e][1,2,4]triazine Scaffolds from Pentafluoropyridine

Annelation reaction between pentafluoropyridine and diaminodihydro substituted pyridine derivatives gave dipyrido[1,2-b:3′,4′-e][1,2,4]triazine systems as major products arising from the initial nucleophilic substitution of more nucleophilic N-amino group

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

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.

Activated Nitriles in Heterocyclic Synthesis. Part III. Synthesis of N-Amino-2-pyridone, Pyranopyrazole and Thiazolopyridine Derivatives

The reaction of 2-cyanoethanoic acid hydrazide and arylidenemalononitrile was studied as a new route for the synthesis of N-amino-2-pyridones.Pyranopyrazole and thiazolopyridine could be prepared from the reaction of arylideneazolones with t