2,7-Naphthyridine is one of the six structural isomers of pyridopyridine, which have a broad spectrum of biological activity such as antimicrobial, antifungal, antimalarial, analgesic, and antiphlogistic [1]. Many of the natural alkaloids containing the 2,7-naphthyridine scaffold show anticancer activity [1]. The various biological properties encourage the synthesis of new 2,7-naphthyridine derivatives. Recently we presented the methods of synthesis and in vitro antitumor screening of novel 1-oxo-6-phenyl-2,7-naphthyridine- 3-carboxylate derivatives [2]. In our studies we have found that the most active were the 2,7-naphthyridine hydrazide derivatives. As a continuation of our research we decided to synthesize a new derivatives by modification of the substituent in position 8 of 2,7-naphthyridine ring. New compounds have been obtained according to the methods described by us before [3]. Heating the ethyl 2-(4-hydroxy-1,3- dioxo-6-phenyl-pyrrolo[3,4-c]pyridin-2-yl)acetate 1 in a fourfold excess of sodium ethoxide resulted in the rearrangement to the ethyl 4,8-dihydroxy-1-oxo-6-phenyl-2H -2,7-naphthyridine-3-carboxylate 2. Ester 2 with hydrazine monohydrate gave appropriate hydrazide 3. The series of Schiff’s bases 4 were synthesized by treating the novel 4,8-dihydroxy-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-   carboxylic acid hydrazide 3 with appropriate aldehydes. Most of newly obtained compounds were qualified by the National Cancer Institute (Bethesda, USA) for in vitro antiproliferative screening against the 60 different human tumor cell lines.

References

[1] A. Wójcicka, E. Wagner, Wiad. Chem. 2011 T.65 nr 3-4, 235-264

[2] E. Wagner, A. Wojcicka, I. Bryndal, T. Lis, Pol. J. Chem. 2009, 83, 207-215

[3] A. M. Wójcicka, E. Wagner, VII Multidisciplinary Conference on Drug Research - MKNOL 2010. Zakopane, Book of abstracts, 39

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1. Synthesis and in vitro anticancer evaluation of the new thiazolo[4,5-d]pyrimidines.
2. Synthesis and antitumor activity of novel 6-phenyl-2,7-naphthyridine derivatives.
3. Synthesis and in vitro anti-hepatitis B and C virus activity of the  new nucleobase analogues containing thiazolo[4,5-d]pyrimidine ring system
4. SYNTHESIS OF NEW DERIVATIVES OF THIAZOLO[4,5-d]PYRIMIDINE AS POTENTIAL ANTITUMOR AGENTS