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Usage

Uses

Used in Pharmaceutical Industry:
2,7-Dimethyl-1,8-naphthyridine is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its unique chemical structure allows it to be incorporated into drug molecules, potentially enhancing their therapeutic properties.
Used in Antimicrobial Applications:
2,7-Dimethyl-1,8-naphthyridine has been studied for its antimicrobial properties. It has the potential to inhibit the growth of various microorganisms, making it a promising candidate for the development of new antimicrobial agents.
Used in Antiviral Applications:
In addition to its antimicrobial activity, 2,7-Dimethyl-1,8-naphthyridine has also been investigated for its antiviral properties. Its ability to interfere with viral replication and infection processes could lead to the development of novel antiviral therapies.
Used in Fluorescent Probes:
2,7-Dimethyl-1,8-naphthyridine has been explored for its potential as a fluorescent probe in biological and environmental applications. Its fluorescent properties allow it to be used for the detection and monitoring of various biological processes and environmental contaminants.
Overall, 2,7-Dimethyl-1,8-naphthyridine is a versatile chemical compound with diverse applications in the pharmaceutical, antimicrobial, antiviral, and fluorescent probe industries. Its unique properties and potential therapeutic effects make it a subject of ongoing research and development in various scientific fields.

Upstream product

• 53051-92-6 2,7-dimethyl-1,8-naphthyridine-4(1H)-one 
• 67-56-1 methanol 
• 84670-41-7 2,7-dimethyl-4-chloro-1,8-naphthyridine 
• 7521-41-7 2-Aminonicotinaldehyde 
• 885276-99-3 2-amino-6-methylpyridine-3-carbaldehyde 
• 67-64-1 acetone 
• 127446-32-6 2,2-Dimethyl-N-(3-formyl-6-methyl-2-pyridinyl)propanamide 
• 86847-79-2 2,2-dimethyl-N-(6-methylpyridin-2-yl)propanamide 
• 86847-64-5 N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide 
• 86847-59-8 2-(pivaloylamino)pyridine 
• 504-29-0 2-aminopyridine 
• 917-54-4 methyllithium 
• 1569-16-0 2-methyl-[1,8]naphthyridine 
• 16867-28-0 2,6-dimethyl-4H-pyrido<1,2-a>pyrimidin-4-one 

Downstream Products

• 1350751-37-9 2,7-bis[2-(N,N-dimethyl-4-aminophenyl)vinyl][1,8]naphthyridine 
• 642988-24-7 (2,7-dimethyl-1,8-naphthyridine)bis(2,6-di(p-tolyl)benzoato)iron(II) 
• 313672-72-9 2,7-bis{2-[2-(1-methyl)benzimidazolylethyl]-N-benzyl-aminomethyl}-1,8-naphthyridine 
• 313672-74-1 2,7-bis(N,N-dibenzyl-aminomethyl)-1,8-naphthyridine 
• 65896-28-8 1,8-naphthyridine-2,7-dicarboxaldehyde 

Relevant academic research and scientific papers

Selective G-quadruplex DNA stabilizing agents based on bisquinolinium and bispyridinium derivatives of 1,8-naphthyridine

Various biologically relevant G-quadruplex DNA structures offer a platform for therapeutic intervention for altering the gene expression or by halting the function of proteins associated with telomeres. One of the prominent strategies to explore the therapeutic potential of quadruplex DNA structures is by stabilizing them with small molecule ligands. Here we report the synthesis of bisquinolinium and bispyridinium derivatives of 1,8-naphthyridine and their interaction with human telomeric DNA and promoter G-quadruplex forming DNAs. The interactions of ligands with quadruplex forming DNAs were studied by various biophysical, biochemical, and computational methods. Results indicated that bisquinolinium ligands bind tightly and selectively to quadruplex DNAs at low ligand concentration (～0.2-0.4 μM). Furthermore, thermal melting studies revealed that ligands imparted higher stabilization for quadruplex DNA (an increase in the Tm of up to 21 °C for human telomeric G-quadruplex DNA and >25 °C for promoter G-quadruplex DNAs) than duplex DNA (ΔTm ≥ 1.6 °C). Molecular dynamics simulations revealed that the end-stacking binding mode was favored for ligands with low binding free energy. Taken together, the results indicate that the naphthyridine-based ligands with quinolinium and pyridinium side chains form a promising class of quadruplex DNA stabilizing agents having high selectivity for quadruplex DNA structures over duplex DNA structures.

Diruthenium complexes with a 1,8-Naphthyridine-based Bis(silyl) supporting ligand: Synthesis and structures of complexes containing RuII2(μ-H)2 and RuI2 cores

We designed a novel naphthyridine-based supporting ligand involving two silyl coordinating moieties at 2,7-positions, t-BuNBSi, for the synthesis of dinuclear metal complexes. Reaction of a ligand precursor t-BuNBSi(H)2 (1) with Ru3(CO)12 gave a di-μ-hydridodiruthenium(II,II) complex (t-BuNBSi)Ru2(μ-H)2(CO)4 (2). Photoirradiation to 2 resulted in the formation of a diruthenium(I,I) complex (t-BuNBSi)Ru2(CO)6 (3). The SiRuRuSi linkage of 2 takes a zigzag arrangement, whereas that of 3 adopts a roughly linear one.

Iron-Catalyzed Water Oxidation: O–O Bond Formation via Intramolecular Oxo–Oxo Interaction

Herein, we report the importance of structure regulation on the O?O bond formation process in binuclear iron catalysts. Three complexes, [Fe2(μ-O)(OH2)2(TPA)2]4+ (1), [Fe2(μ-O)(OH2)2(6-HPA)]4+ (2) and [Fe2(μ-O)(OH2)2(BPMAN)]4+ (3), have been designed as electrocatalysts for water oxidation in 0.1 M NaHCO3 solution (pH 8.4). We found that 1 and 2 are molecular catalysts and that O?O bond formation proceeds via oxo–oxo coupling rather than by the water nucleophilic attack (WNA) pathway. In contrast, complex 3 displays negligible catalytic activity. DFT calculations suggested that the anti to syn isomerization of the two high-valent Fe=O moieties in these catalysts takes place via the axial rotation of one Fe=O unit around the Fe-O-Fe center. This is followed by the O?O bond formation via an oxo–oxo coupling pathway at the FeIVFeIV state or via oxo–oxyl coupling pathway at the FeIVFeV state. Importantly, the rigid BPMAN ligand in complex 3 limits the anti to syn isomerization and axial rotation of the Fe=O moiety, which accounts for the negligible catalytic activity.

Cooperative H2 Activation on Dicopper(I) Facilitated by Reversible Dearomatization of an “Expanded PNNP Pincer” Ligand

A naphthyridine-derived expanded pincer ligand is described that can host two copper(I) centers. The proton-responsive ligand can undergo reversible partial and full dearomatization of the naphthyridine core, which enables cooperative activation of H2 giving an unusual butterfly-shaped Cu4H2 complex.

Elaboration of 1,8-naphthyridine-2,7-dicarboxaldehyde into novel 2,7-dimethylimine derivatives

The known 1,8-naphthyridine-2,7-dicarboxaldehyde was prepared by SeO2 oxidation of 2,7-dimethyl-1,8-naphthyridine. The dimethylated naphthyridine molecule was assembled from an adaptation of the Skraup synthesis using 2-amino-6-methylpyridine and crotonaldehyde to afford a reproducible 37% yield, and constitute a significant advance over the literature of this reaction. The condensation of 1,8-naphthyridine-2,7-dicarboxaldehyde with various primary amines (R = -C6H11, -CH2C6H5, -C(CH3)3, -C10H15, and CH2CH2SCH2CH3) in alcohol affords diimines l(a-e). The inherent crystallinity of 1(a-e) affords pure compounds in reasonable to excellent yields (ca. 70%) after evaporation of solvent and recrystallization. The anticipated spectroscopic features of (N=C-H) 1H nmr shift and v(C=N) in the ir spectrum appear around 8.50 δ and 1640 cm-1, respectively, for the series 1(a-e). These novel naphthyridines typically display the signature 1H nmr doublets at ca. 8.15-8.30 δ ascribed to the 3 and 4 naphthyridine protons, consistent with a mirror plane (through the quaternary carbons) perpendicular to the naphthyridine plane, and syn, syn relationships of the naphthyridine moiety with each imine nitrogen lone pair. Complexation studies of 1(a-e) with transition metals of biological relevance such as copper(I) and copper(II) will be reported elsewhere.

Photoinduced Trifluoromethylation of Arenes and Heteroarenes Catalyzed by High-Valent Nickel Complexes

We describe a series of air-stable NiIII complexes supported by a simple, robust naphthyridine-based ligand. Access to the high-valent oxidation state is enabled by the CF3 ligands on the nickel, while the naphthyridine exhibits either a monodentate or bidentate coordination mode that depends on the oxidation state and sterics, and enables facile aerobic oxidation of NiII to NiIII. These NiIII complexes act as efficient catalysts for photoinduced C(sp2)?H bond trifluoromethylation reactions of (hetero)arenes using versatile synthetic protocols. This blue LED light-mediated catalytic protocol proceeds via a radical pathway and demonstrates potential in the late-stage functionalization of drug analogs.

Nitroacetonitrile and Its Synthetic Equivalents

Nitroacetonitrile (NAN) serves as a cyano(nitro)methylating agent facilitating the construction of polyfunctionalized compounds; however, its explosive property is a significant drawback in terms of practical handling. Alkali metal salts of NAN are therma

A four-hydrogenated 1, 8 - naphthyridine apperception composition preparation method and its prepared chiral products

The invention discloses a preparation method of a tetrahydro 1, 8-naphthyridine compound. The preparation method comprises the following steps: under the existence of a chiral catalyst, enabling a compound with the structure shown in the formula (1) (in the description) and hydrogen to be subjected to addition reaction, wherein the chiral catalyst is a coordination compound with the structure shown in the formula (2) (in the description). The invention further provides a chiral product of the tetrahydro 1, 8-naphthyridine compound, prepared through the preparation method. According to the invention, the proper compound with the structure shown in the formula (1) (in the description) is used as a substrate, and the proper coordination compound with the structure shown in the formula (2) (in the description) is used as the chiral catalyst to perform selective hydrogenation reduction on 1, 8-naphthyridine compound with the structure shown in the formula (1) by adopting hydrogen, so that the chiral product of the tetrahydro 1, 8-naphthyridine compound is prepared with low cost. The chiral product of the tetrahydro 1, 8-naphthyridine compound can be used as a biologically active compound and a structural building block of a chiral drug.

Ruthenium-Catalyzed Enantioselective Hydrogenation of 1,8-Naphthyridine Derivatives

The first asymmetric hydrogenation of 2,7-disubstituted 1,8-naphthyridines catalyzed by chiral cationic ruthenium diamine complexes has been developed. A wide range of 1,8-naphthyridine derivatives were effectively hydrogenated to give 1,2,3,4-tetrahydro-1,8-naphthyridines with up to 99% ee and full conversions. The method provides a practical and facile approach to the preparation of valuable chiral heterocyclic building blocks and useful motifs for a new kind of P,N-ligand.

Borane-catalyzed metal-free hydrogenation of 2,7-disubstituted 1,8-naphthyridines

Metal-free hydrogenation of 2,7-disubstituted 1,8-naphthyridines was successfully realized for the first time using in situ generated borane catalysts under mild conditions to furnish 1,2,3,4-tetrahydro-1,8-naphthyridine derivatives in 83-98% yields. Significantly, up to 74% ee was achieved for the corresponding asymmetric hydrogenation reactions.