220729-07-7Relevant academic research and scientific papers
Ethyl 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylates by a tandem S NAr-addition-elimination reaction
Bunce, Richard A.,Nammalwar, Baskar
experimental part, p. 658 - 663 (2012/08/27)
A series of N-substituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate esters has been prepared in two steps from ethyl 2-(2-chloronicotinoyl)acetate. Treatment of the β-ketoester with N,N-dimethylformamide dimethyl acetal in N,N-dimethylformamide (DMF) gave a 95% yield of the 2-dimethylaminomethylene derivative. Subsequent reaction of this β-enaminone with primary amines in DMF at 120oC for 24 h then afforded the target compounds in 47-82% yields by a tandem SNAr-addition-elimination reaction. Synthetic and procedural details as well as a mechanistic rationale are presented.
Optimization and structure-activity relationship of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides: Identification of MK-0873, a potent and effective PDE4 inhibitor
Guay, Daniel,Boulet, Louise,Friesen, Richard W.,Girard, Mario,Hamel, Pierre,Huang, Zheng,Laliberte, France,Laliberte, Sebastien,Mancini, Joseph A.,Muise, Eric,Pon, Doug,Styhler, Angela
scheme or table, p. 5554 - 5558 (2009/06/18)
A SAR study of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides is described. Optimization of the series was based on in vitro potency against PDE4, inhibition of the LPS-induced production of TNF-α in human whole blood and minimizing affinity f
