4974-50-9

Basic information

• Product Name: 2-cyano-N-(cyclohexylideneamino)acetamide
• CAS NO: 4974-50-9
• Molecular Formula: C₉H₁₃N₃O
• Molecular Weight: 179.222
• Mol File: 4974-50-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.17g/cm³
• CAS DataBase Reference: 2-cyano-N-(cyclohexylideneamino)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-N-(cyclohexylideneamino)acetamide(4974-50-9)
• EPA Substance Registry System: 2-cyano-N-(cyclohexylideneamino)acetamide(4974-50-9)

Safety Data

• Hazardous Substances Data: 4974-50-9(Hazardous Substances Data)

Upstream product

• 140-87-4 Cyanoacetohydrazide 
• 108-94-1 cyclohexanone 

Downstream Products

• 28748-99-4 3-phenyl-4,5,6,7-tetrahydro-1H-indazole 
• 58413-04-0 3-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-indazole 
• 58413-02-8 3-(4-chloro-phenyl)-4,5,6,7-tetrahydro-1⁽²⁾H-indazole 

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.

Utility of cyano acid hydrazide in heterocyclic chemistry: A new route for the synthesis of new 1,2,4-triazolo[1,5-a]pyridines and 1,2,4-triazolo[1,5-a]isoquinolines

Cyano acid hydrazide 1 was condensed with cyclohexanone in refluxing ethanolic piperidine to yield the hydrazone 4. Compound 4 reacts with arylidines 5a-i to yield the 1,2,4-triazolo[1,5-a]pyridines 7a-i. Compound 4 also reacts with mixtures of aliphatic aldehydes and different active methylene reagents to yield 1,2,4-triazolo[1,5-a]pyridines 8a-d. Similarly reaction of 4 with arylazomalononitrile to yield the triazolopyridines 10a-d. Reaction of 4 with aromatic aldehydes gives 12a-e. Compound 8a reacts with elemental sulfur to yield the thieno-1,2,4-triazolopyridine 13. This underwent cycloaddition with acrylonitrile, ω-nitrostyrene, chalcone, N-phenylmalemide, dimethylacetylenedicarboxylate and tetracyanoethylene yielding the isoquinolines 15-18. All new compounds have been characterized by their IR, 1H NMR and mass spectra.