55243-02-2

Usage

Uses

Used in Organic Synthesis:
2,7-Dichloro-1,8-naphthyridine is used as a synthetic intermediate for the development of various chemical compounds. Its unique structure and reactivity make it a valuable component in the creation of complex organic molecules, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,7-Dichloro-1,8-naphthyridine is used as a key building block for the synthesis of novel therapeutic agents. Its chemical properties allow for the development of new drugs with potential applications in treating various diseases and medical conditions.
Used in Chemical Industry:
The chemical industry utilizes 2,7-Dichloro-1,8-naphthyridine as a starting material for the production of various specialty chemicals, including dyes, pigments, and advanced materials with unique properties. Its versatility in organic synthesis contributes to the development of innovative products and technologies.

InChI:InChI=1/C8H4Cl2N2/c9-6-3-1-5-2-4-7(10)12-8(5)11-6/h1-4H

Upstream product

• 106582-47-2 2-hydroxy-7-methoxy-1,8-naphthyridine 
• 49655-93-8 2,7-dihydroxy-1,8-naphthyridine 
• 141-86-6 2.6-diaminopyridine 
• 617-48-1 malic acid 
• 53788-35-5 2-methoxy-7-amino-1,8-naphthyridine 
• 15944-33-9 2-chloro-7-amino-1,8-naphthyridine 
• 1931-44-8 2-amino-7-hydroxy-1,8-naphthyridine 

Downstream Products

• 122768-42-7 2,7-bis(diphenylphosphino)-1,8-naphthyridine 
• 145325-89-9 2,7-bisamino-1,8-naphthyridine 
• 467435-77-4 2,7-bis-(1-tert-butoxycarbonylpyrrol-2-yl)ethynyl-1,8-naphthyridine 
• 889679-04-3 2,7-bis(α-pyridylamino)-1,8-naphthyridine 
• 335594-22-4 N,N'-bisbenzyl-2,7-diamino-1,8-naphthyridine 
• 14903-78-7 2,7-dimethyl-[1,8]naphthyridine 
• 122768-48-3 2,7-Bis-(diphenyl-phosphinoyl)-[1,8]naphthyridine 
• 846031-23-0 2-benzyloxy-7-chloro-[1,8]naphthyridine 
• 1327279-36-6 2,7-bis(benzyloxy)-1,8-naphthyridine 
• 85575-97-9 2,7-diphenyl-[1,8]-naphthyridine 
• 1426415-52-2 2,7-di(p-tolyl)-1,8-naphthyridine 
• 1426415-53-3 2,7-bis(2,5-dimethoxyphenyl)-1,8-naphthyridine 
• 1426415-55-5 2,7-bis(4-methoxyphenyl)-1,8-naphthyridine 
• 1426415-56-6 1,1'-(4,4-(1,8-naphthyridine-2,7-diyl)bis(4,1-phenylene))diethanone 

Relevant academic research and scientific papers

A naphthyridine-indole ligand for selective stabilization of G-quadruplexes and conformational conversion of hybrid topology

The development of ligands to stabilize G-quadruplexes (G4s) or induce G4s to transition from metastable topology to stable topology is a potential strategy for inhibiting cancer cell proliferation. In this study, a novel G-quadruplex (G4) ligand based on a naphthyridine scaffold with two indole pendants, L5-DA, is reported to convert hybrid to the parallel topology. Circular dichroism (CD) and fluorescence spectroscopies were used to investigate the interactions between L5-DA and G4s. The CD spectra revealed that the L5-DA induced the conformational conversion from hybrid topologies to parallel topologies with a melting temperature increase of more than 30 °C. According to F?rster resonance energy transfer assays, the presence of excess duplex competitor had no effect on the ligand-induced stabilization of the hybrid topology, confirming the L5-DA's selectivity for G4s over ds26. With IC50 values of 4.3 μM, the ligand showed significant cytotoxicity against HeLa cells and effectively induced growth inhibition and apoptosis in HeLa cells. Immunofluorescence microscopy revealed an increase in BG4 foci in the presence of the L5-DA, confirming ligand-induced G4s stabilization in HeLa cells. According to these results, the combination of naphthyridine and indole scaffold was an effective design strategy for G4s stabilization and conformational conversion of metastable G4 topology for inhibiting cancer cell growth.

Chiral 1,8-naphthyridine based ligands: Syntheses and characterization of Di- and tetranuclear copper (I) and silver (I) complexes

Oxazoline and camphor-pyrazole units are introduced on the 1,8-naphthyridine scaffold to access chiral ligands L1, L2 and L3. Metalation of these chiral ligands with Cu(I) and Ag(I) precursors afforded di- and tetranuclear complexes [Cu4I4(L1)2] (1), [Cu4I4(L2)2] (2), [Cu2I2(L3)] (3), [Cu2I(L2)2](OTf) (4), [Ag2(L1)2](OTf)2 (5) and [Ag4(L2)4Br](OTf)3 (6), containing [M4Xn] (n = 1,4 and X = Br, I) or [M2Xn] (n = 0, 1, 2 and X = I) core. All complexes are structurally characterized. Naphthyridine-derived ligands reveal bridge-chelate coordination motif and hold two metal centers in close proximity. The tetranuclear complexes are dimer of dinuclear complexes bridged by the halides. Electronic absorption and emission spectra of copper complexes are reported. Catalytic utility of all complexes are examined for asymmetric transformations but they showed poor activity probably due to limited solubility and coordinative saturation at the metal centers. The best results are obtained with [L3/Cu salt] combination for cyclopropanation of styrene, N–H bond insertion and nitroaldol (Henry) reactions with very low enantioselectivity.

Suzuki-miyaura reactions of 2,7-dichloro-1,8-naphthyridine

2,7-Diaryl- and 2,7-dialkenyl-1,8-naphthyridines were prepared in high yields by Suzuki-Miyaura reactions of 2,7-dichloro-1,8-naphthyridines. While most of the products proved to be not or only weakly fluorescent, we observed a strong fluorescence in case of 2,7-bis(4-methoxyphenyl)-1,8-naphthyridine containing two electron-donating aryl groups. Georg Thieme Verlag Stuttgart - New York.

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE

Provided is a novel heterocyclic compound which is useful as a material for an organic electroluminescent device. The heterocyclic compound is represented by the general formula [I]: wherein X represents a nitrogen atom or a carbon atom; Y represents O or S; R1 and R2 each represent, independently of one another, a group selected from the group consisting of a substituted or unsubstituted alkyl group and the like; a represents 0 or more and 3 or less; b represents 0 or more and 3 or less; and Ar1 represents a substituted or unsubstituted heterocyclic ring or the like; and n represents an integer of 2 to 10.

1,8-Naphthyridine compound and organic light-emitting device using the same

Provided a novel 1,8-naphthyridine compound represented by the following general formula [I]: wherein R1 to R6 each represent one selected from the group consisting of a hydrogen atom; an alkyl group, an aralkyl group, an aryl group, a heterocyclic group, a condensed polycyclic aromatic group, a condensed polycyclic heterocyclic group and an aryloxy group which may be substituted; a substituted amino group; a halogen atom; a trifluromethyl group; and a cyano group, and may be the same as or different from one another, provided that at least two of R1 to R6 each represent one selected from the group consisting of an aralkyl group, an aryl group, a heterocyclic group, a condensed polycyclic aromatic group, a condensed polycyclic heterocyclic group and an aryloxy group which may be substituted; and a substituted amino group.

Ruthenium complexes with naphthyridine ligands. Synthesis, characterization and catalytic activity in oxidation reactions

New ruthenium complexes with 1,8-naphthyridine (napy) or derivatives thereof as ligands have been prepared and characterized. Three groups of complexes were obtained. The first consists of three dinuclear ruthenium complexes with two ligands (1,8-naphthyridine and pyridopyrazine) co-ordinated to two ruthenium ions in a bridging fashion. The second consists of two ruthenium dinuclear complexes having one ligand (2,7-dimethoxy-or 2,7-dichloro-1,8-naphthyridine, abbreviated to dmnapy and dcnapy respectively) co-ordinated to two ruthenium atoms. Proton NMR spectra for both complexes in aqueous solution and in acetonitrile revealed the conversion of a symmetrical form, suggesting dinucleating behaviour of the ligand, into an asymmetrical form, suggesting mononucleating behaviour of the ligand. The third group consists of a mono- and a di-nuclear complex with the ligand 2,7-di(phenylazo)-1,8-naphthyridine. The catalytic activity of the novel naphthyridine complexes in oxidation reactions has been studied. The catalytic oxidation of alcohols and the epoxidation of trans-stilbene were examined and the different reaction rates and selectivities are discussed in a comparative way. The active high-valent species resulting from the [Ru2(napy)2(H2O)4Cl(OH)] 4+ complex is discussed in more detail.

Chemistry of Heterocyclic Compounds. 61. Synthesis and Conformational Studies of Macrocycles Possessing 1,8- or 1,5-Naphthyridino Subunits Connected by Carbon-Oxygen Bridges

Polyethereal macrocycles were prepared from both 2,6-dichloro-1,5-naphthyridine (2) and 2,7-dichloro-1,8-naphthyridine (6).The "cross-the-face" structures of 1:1 macrocycles 7, derived from 2, were confirmed by NMR.The 2,7-(1,8-naphthyridino) macrocyclic structures 9 and 10 were also supported by NMR data which were indicative of diminished N-electron density, when compared to the parent 1,8-naphthyridine.Template reactions did not appreciably enhance product yields.The X-ray crystal structure of 1:1 macrocycle 9b was conducted and showed that the imidate moieties possess a nearly 0 deg dihedral angle and that the naphthyridine subunit exhibits marginal deviation from planarity.