680215-01-4

Upstream product

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

Downstream Products

• 1184721-96-7 C₁₆H₁₁N₅O₃ 

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.

A three component one-pot synthesis of N-amino-2-pyridone derivatives catalyzed by KF-Al2O3

Synthesis of 1,6-diamino-4-phenyl-3,5-dicyano-2-pyridone derivatives via a one-pot, three-component reaction of aryl aldehydes, malononitrile, and cyanoacetic hydrazide at room temperature using KF-Al2O3 as a recyclable catalyst have been developed. The reaction proceeds through the initial Knoevenagel condensation between aldehyde and malononitrile in the presence of KF-Al2O3 to form the benzylidene derivative which then undergoes Michael addition with cyanoacetic hydrazide followed by intramolecular cyclization of the resulting intermediate to produce the N-amino-2-pyridones in good to excellent yields. The structure of the synthesized compounds were characterized and established on the basis of their spectral data analysis and single-crystal XRD analysis.

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 convenient synthesis of [1,2,4]triazolo[1,5-a]pyridines and 1,8-naphthyridine of analgesic and anti-inflammatory profiles

Starting from 1,6-diamino-3,5-dicyano-4-aryl-2-pyridones, substituted triazolo[1,5-a]pyridines and 1,8-naphthyridine derivatives have been synthesized. All the synthesized compounds were fully characterized by spectroscopic, physical data, and elemental analyses. Some of triazolo[1,5-a]pyridines were tested with respect to their analgesic and anti-inflammatory activities. All tested compounds exhibited analgesic activities comparable or superior to Valdecoxib. The anti-inflammatory activity was present in all the tested compounds as well and exceeded that of Hydrocortisone.