Among six structural isomers of naphthyridines, the synthesis and activity of the 2,7 isomer derivatives have not yet been thoroughly investigated. The various pharmacological properties of 2,7-naphthyridine derivatives encourage the search for new methods of their preparation. In the first step, we have determined a way of synthesizing ethyl 8-R-4-hydroxy-1-oxo-6-phenyl-1,2-dihydro- 2,7-naphthyridine-3-carboxylates by the Claisen-Dieckman alkoxide-induced rearrangement, according the method reported in our previous paper [1]. Heating obtained before the new pyrrolo[3,4-c]pyridine derivatives in a fourfold excess of sodium ethoxide resulted in the rearrangement to a naphthyridine ring and also the transestrification and the substitution of the ethoxycarbonylmethoxy to the ethoxy group. Similarly, from the 4-methyl-2-(2-oxo-2-phenyl-ethyl)-6-phenyl-pyrrolo[3,4-c]pyridine- 1,3-dione the 3-benzoyl-4-hydroxy-8-methyl-6-phenyl-2H-2,7- naphthyridin-1-one was obtained. Subsequently, new 2,7-naph- thyridine derivatives were synthesized by the hydrolysis, ammonolysis, and reaction with hydrazine of the 2,7-naphthyridine esters. A series of Schiff's bases were also produced by treating the obtained hydrazides with the aldehydes. Most of newly synthesized compounds were qualified by the NCI (Bethesda, USA) for in vitro antitumor screening. The compounds were evaluated against the 60 different human tumor cell lines, representing melanoma, leukemia, and cancers of the breast, CNS, colon, ovary, kidney, prostate and non-small cell lung. The tested compounds showed variable antitumor activity. The most active were the 2,7-naphthyridine hydrazide derivatives.

The structures of the new compounds were confirmed by elemental analysis and NMR and IR spectra.

Reference

[1] E. Wagner, A. Wójcicka, I. Bryndal, T. Lis, Polish J. Chem., 2009, 83, 207-215.

1. PRESENTATION: Synthesis and antitumor activity of novel 6-phenyl-2,7-naphthyridine derivatives., Microsoft Office Document, 0MB
2. PRESENTATION: Synthesis and antitumor activity of novel 6-phenyl-2,7-naphthyridine derivatives., Microsoft Office Document, 0MB

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