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1 2009

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Synthesis, Structure, and Pharmacological Screening of 2,7-Naphthyridine Derivatives

Wagner E., Wójcicka A., Bryndal I., Lis T.

Polish Journal of Chemistry

2009

Vol. 83, nr 2

207-215

An attempt to rearrange pyrrolo[3,4-c]pyridine-1,3-diones to the 2,7-naphthyridine ring under the conditions, described in only one report [1], gave compounds 7-9, but did not yield the expected 2,7- or 2,6-naphthyridine isomers. Important for the synthesis of the naphthyridine ring from pyrrolo[3,4-c]pyridine was that, of the two possible isomers, only 2,7- not 2,6-naphthyridine was obtained. Ethyl (4-R'-1,3- dioxo- 6-phenyl-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)acetate (5, 6, 10) treated with sodium ethoxide was rearranged by the Claisen-Dieckmann reaction to ethyl 4-hydroxy-8-R'-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-carboxylate (13, 14), where R' = methyl or ethoxy. The structures of the new compounds were confirmed by elemental analysis and NMR and IR spectra. The structure of 14 was also determined by X-ray crystallography to prove the presence of 2,7-naphthyridine isomer. The in vitro anticancer activities of the final 2,7-naphthyridines were tested at the US NCI (Bethesda, MD). Compound 13 exhibited cytostatic activity in vitro.