108958-64-1

Upstream product

• 103607-65-4 1-Phenyl-4-oxo-5-cyano-6-(β-dimethylaminovinyl)-1,4-dihydropyrimidine 
• 91255-14-0 α-Cyano-β-N-phenylaminocrotonamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 62321-92-0 α-cyano-β-dimethylaminocrotonamide 
• 62-53-3 aniline 
• 120651-05-0 α-cyano-β-dimethylaminocrotonamide 
• 120650-99-9 (Z)-2-Cyano-3-phenylamino-but-2-enoic acid amide 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 103607-65-4 1-phenyl-5-cyano-6-(β-dimethylamino)vinyl-4-pyrimidone 

Downstream Products

• 1312548-56-3 CH₆N₄*C₁₃H₈ClN₃O₂ 
• 352554-01-9 5-[(4-hydroxy-3-methoxybenzylidene)hydrazonomethyl]-2-oxo-4-phenylamino-1,2-dihydropyridine-3-carbonitrile 
• 371928-77-7 5-benzylidenehydrazonomethyl-2-oxo-4-phenylamino-1,2-dihydropyridine-3-carbonitrile 
• 352554-00-8 3-cyano-5-(2-cyano-2-ethoxycarbonylvinyl)-2-oxo-4-(phenylamino)-1,2-dihydropyridine 
• 352553-54-9 3-cyano-5-(hydrazonomethyl)-2-oxo-4-(phenylamino)-1,2-dihydropyridine 
• 948035-17-4 3-cyano-5-hydroxymethyl-2-oxo-4-phenylamino-1,2-dihydropyridine 

Relevant academic research and scientific papers

CPAP-TUBULIN MODULE

The invention relates to CPAP-tubulin inhibitors having the general formula (1) or a physiologically acceptable salt thereof; and their use as cancer therapeutics.

Synthesis and hydrolytic cleavage of 1-aryl-5-cyano-6-(2- dimethylaminovinyl)-4-oxo(thioxo)-1,4-dihydropyrimidines

1-Aryl-5-cyano-6-(2-dimethylaminovinyl)-4-oxo-1,4-dihydropyrimidines and their 4-thioxo analogs, which were prepared in three steps from cyanoacetamide and cyanothioacetamide, respectively, were subjected to hydrolysis. In aqueous AcOH, hydrolysis of N-(dimethylaminomethylene)-2-cyano-5-dimethylamino-2,4- pentadieneamide derivatives containing amino groups at position 3 afforded formylpyridones. The reaction of 2-cyano-3-dimethylaminothiocrotonamide with DMF dimethyl acetal gave rise to 3-cyano-4-dimethylamino-2-methylthiopyridine.

Study of the reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine with nucleophilic reagents

The reactions of 3-chloro-4-cyanobenzo[b][1,6]naphthyridine (4) with S-, C-, and N-nucleophiles afford stable σ-adducts at position 10. In the base-catalyzed reactions of compound 4 with thiols, the resulting σ-complexes are rearranged into sulfides 14a - c. Sulfides 14b,c undergo the Thorpe - Ziegler cyclization to give 1-aminobenzo[b]thieno[2,3-h][1,6]naphthyridine derivatives 15a,b. The reaction of naphthyridine 4 with aniline affords a mixture of σ-adducts of the C - N and C - C types, while those with aliphatic amines yield 3-amino derivatives 17a - c. In the presence of H2O2, benzonaphthyridine 4 adds peroxycarboxylic acids to give compounds 8a,b. In alkaline medium, adduct 8a is rearranged into 4-aminopyridine-3-carbaldehyde derivative 10.

ACETALS OF LACTAMS AND ACID AMIDES. 47.* INVESTIGATION OF THE BEHAVIOR OF SUBSTITUTED 6-(β-DIMETHYLAMINO)VINYL-4-PYRIMIDINONES IN ACID MEDIA. SYNTHESIS OF 3-CYANO-4-ANILINO-5-FORMYL-2-PYRIDONE AND 3-CHLORO-4-CYANOBENZONAPHTHYRIDINE

The hydrolysis of 1-substituted 5-cyano-6-(β-dimethylamino)vinyl-4-pyrimidinones in acidic media was studied.It was shown that the 1-benzyl derivative is converted to a mixture of α-cyano-4β-benzylamino-crotonamide and 3-cyano- and 3-carbamido-4-benzyl-amino-2-pyridones.The principal product in the hydrolysis of the 1-phenyl derivative is 3-cyano-4-anilino-5-formyl-2-pyridone.Cyclization of the latter by heating in phosphorus oxychloride leads to 3-chloro-4-cyanobenzonaphthyridine.