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Syntezy pochodnych 2,7-naftyrydyny

Wójcicka A.

Wiadomości Chemiczne

2017

[Z] 71, 5-6

349--379

2,7-Naphthyridines have been the least known from all of the six structural isomers of pyridopyridines. The broad spectrum of biological activity of 2,7-naphthyridine derivatives [1] is the main of reason for obtaining of the new compounds containing this scaffold (Fig. 1). Gabriel and Colman were the first to obtain isomer 2,7-naphthyridine in 1902 and they called it ‘copiryne’ (Fig. 2) [2]. The goal of this study is the presentation of various methods for the preparation of 2,7-naphthyridine derivatives. Compounds containing copyrine scaffold can be obtained from a different substrates, but that synthesis may be classified into three main categories: from pyridine derivatives, from quinoline derivatives and from other compounds. Most of 2,7-naphthyridines have been synthesized by cyclocondensation (Scheme 5, 7–10, 13–14, 16–18, 20, 28–29, 32, 35–36) or intramolecular cyclization (Scheme 1–4, 6, 11–12, 15, 19, 21–25, 30–31, 33–34, 38) of pyridine derivatives by annulation of the other pyridine ring [3–24, 27–31]. Intramolecular rearrangement of pyrrolo [3,4-c] pyridines (Scheme 26–27) and pyrano [3,4-c] pyridine or thiopyrano [3,4-c] pyridine (Scheme 35–37) also gave the 2,7-naphthyridine scaffold [32-34]. There are also many syntheses of benzo[c][2,7]naphthyridine, benzo [f] [2,7] naphthyridine or benzo [ c,f] [2,7] naphthyridine scaffolds, in which the substrates are quinoline derivatives (Scheme 39–48) [35–43]. 2,7-naphthyridines have been least often obtained by cyclocondensation of non-cyclic substrates (Scheme 49–53) [44–49].

Aktywność biologiczna pochodnych 2,7-naftyrydyny

Wójcicka A., Wagner E.

Wiadomości Chemiczne

2011

[Z] 65, 3-4

235-264

2,7-Naphthyridine is one of the six structural isomers of pyridopyridines. More than one hundred years ago, Gabriel and Colman discovered the isomer 2,7-naphthyridine, and named it “copiryne” [3]. From among of all naphthyridines, the synthesis and properties of the copyrine derivatives have not yet been thoroughly investigated. This paper reviews the synthetic and natural 2,7-naphthyridine derivatives which have been reported to possess various biological activity. A large number alkaloids containing the 2,7-naphthyridine scaffold have been isolated from plants and marine organisms [13–18]. The natural marine alkaloids can be classified into two groups. The bicyclic lophocladines were isolated from the red alga Lophocladia sp. [12]. The pyridoacridines represent a large and growing class the polycyclic alkaloids from sponges, ascidians or tunicates [15, 16]. Many of this natural compounds exhibited cytotoxic, antibacterial, antiviral, antifungal and sedative activity. The broad spectrum of biological activity of copyrine alkaloids is the main of reason for the preparation of new 2,7-naphthyridine derivatives also by the synthetic route. So far, about fifty different methods of synthesizing the 2,7-naphthyridine ring have been published. This study described synthesis only biologically active 2,7-naphthyridine analogues. Biological investigations have shown that copyrine derivatives have a wide spectrum of actions. Antitumor, antimicrobial, analgesic and anticonvulsion activities have been found. Most of 2,7-naphthyridine derivatives have been studied as antitumor agents. Many papers described synthesis and pharmacological properties the best active and highly selective PDE5 inhibitor (T-0156) [55]. So far, none of 2,7-naphthyridine derivatives has been applied as a drug.