6492-86-0

Usage

Uses

Used in Dye and Pigment Synthesis:
4-Amino-1,8-naphthalic anhydride is utilized as a key building block in the synthesis of various dyes and pigments, including fluorescent whitening agents and coloring agents for textiles and plastics. Its chemical structure allows for the creation of a wide range of colorants with diverse properties, enhancing the colorfastness and brightness of the final products.
Used in Pharmaceutical Intermediates:
In the pharmaceutical industry, 4-Amino-1,8-naphthalic anhydride is employed as a reagent in the preparation of pharmaceutical intermediates. Its unique chemical properties enable the development of new drug candidates with potential therapeutic applications, contributing to the advancement of medicinal chemistry.
Used in Organic Compound Preparation:
4-Amino-1,8-naphthalic anhydride is also used in the preparation of other organic compounds, serving as a versatile intermediate for the synthesis of various chemical entities. Its presence in the synthesis process can lead to the development of new materials with specific properties, such as improved stability or reactivity, broadening the scope of applications in various industries.

InChI:InChI=1/C12H7NO3/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(14)16-12(8)15/h1-5H,13H2

Upstream product

• 6642-29-1 4-nitronaphthalic-1,8-anhydride 
• 7647-01-0 hydrogenchloride 
• 602-87-9 4-nitroacenaphthene 
• 34087-02-0 2-nitro-1,8-naphthalic anhydride 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 1262149-88-1 6-azido-1H,3H-benzo[de]isochromene-1,3-dione 
• 81-84-5 1,8-Naphthalic anhydride 
• 83-32-9 acenaphthene 

Downstream Products

• 58232-21-6 6-amino-2-cyclohexyl-benz[de]isoquinoline-1,3-dione 
• 6357-99-9 6-amino-1,3-dioxo-1H,3H-benz[de]isochromene-5-sulfonic acid 
• 462657-77-8 4-dabsylamino-1,8-naphthalic anhydride 
• 722541-27-7 4-(1,3-dioxo-1H,3H-benzo[de]isochromen-6-ylazo)-3-hydroxy-naphthalene-2-carboxylic acid (4-methoxy-phenyl)-amide 
• 19125-99-6 2-butyl-6-(butylamino)-1H-benz(de)isoquinoline-1,3(2H)-dione 
• 10166-30-0 6-amino-1,3-dioxo-2-p-tolyl-2,3-dihydro-1H-benz[de]isoquinoline-5-sulfonic acid 
• 1172582-40-9 6-amino-2-(prop-2-yn-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 1267672-96-7 C₂₆H₂₃N₃O₉ 
• 1269171-09-6 C₃₃H₄₂N₂O₅Si 

Relevant academic research and scientific papers

Reduction of 4-azidonaphthalimide with different phosphine ligands and exploration of their spectroscopic properties

A convenient, high efficient method for the reduction of 4-azidonaphthalimide to 4-aminonaphthalimide (1) by using PMe3 has been developed. Several 4-substituted 1,8-naphthalimide iminophosphoranes were also successfully synthesized. Their structures were characterized by NMR and MS analyses. The structures of compounds 2 and 3 were also confirmed by single crystal X-ray diffraction analysis. Their optoelectronic properties of these naphthalimides were investigated. The results indicated that their optical properties could be tuned by different phosphine ligands, which make them novel potential organic luminescent materials.

The effects of varying the substituent and DNA sequence on the stability of 4-substituted DNA-naphthalimide complexes

DNA duplexes are stabilized by many interactions, one of which is stacking interactions between the nucleic acid bases. These interactions are useful for designing small molecules that bind to DNA. Naphthalimide intercalators have been shown to be valuable anti-cancer agents that stack between the DNA bases and exhibit stabilizing effects. There is a continued need to design intercalators that will exhibit these stabilizing effects while being more selective toward DNA binding. This work investigates 4-substituted naphthalimides with varying functional groups and their interactions with nucleic acid duplexes. Mode of binding was determined via wavelength scans, circular dichroism, and viscosity measurements. Optical melting experiments were used to measure the absorbance of the sample as a function of temperature. The Tm values derived from the DNA duplexes were subtracted from the Tm values derived from the DNA-intercalator complexes, resulting in ΔTm values. The ΔTm values demonstrated that the substituents on the intercalator affect the stability of the DNA-intercalator complex. From the results of this study and comparison to results from previous work, we conclude that the substituent type and position on the core intercalator molecule affect the stability of the complex it forms with DNA.

A GSH-responsive PET-based fluorescent probe for cancer cells imaging

An efficient PET-based probe, in which the ferrocene quencher and the naphthalimide fluorophore are linked by a disulfide bond, has been developed. This probe can be activated by GSH with fluorescence a turn-on response for blocking the PET process. In addition, it was successfully applied for distinguishing cancer cells from normal cells

A novel glutathione-Triggered theranostic prodrug for anticancer and imaging in living cells

A novel theranostic prodrug was designed and synthesized by conjugating a naphthalimide derivative with Vitamin D2via a disulfide linker. The prodrug featured a highly selective detection process for glutathione (GSH) and showed a red-shifted f

Enhanced nonradiative decay in aqueous solutions of aminonaphthalimide derivatives via water-cluster formation

The photophysics of two derivatives of 4-aminonaphthalimide have been studied in aqueous, ethanolic, and mixed aqueous/ethanolic solvents, including both normal and deuterated solvents. It is found that the fluorescence quantum yield and lifetime both decrease with increased water content of the solvent and that this is entirely due to increased nonradiative decay, the radiative rate constant being virtually independent of the solvent composition. It is proposed that a mechanism involving the formation of a hydrogen-bonded water cluster is responsible for the observed behavior with the excitation energy of the naphthalimide being distributed amongst the stretching vibrations of the water cluster. The increase in the rate of nonradiative decay is greatly reduced in deuterated solvent mixtures in accord with Siebrand's theory of radiationless processes.

Purification and characterization of a nitroreductase from the soil bacterium Streptomyces mirabilis

A NADH-dependent nitroreductase from an efficient nitro-reducing soil bacterium, Streptomyces mirabilis DUT001, was isolated and characterized. The enzyme was purified to near homogeneity using ammonium sulfate precipitation, ion exchange chromatography, and gel filtration chromatography. The native enzyme was estimated by gel filtration to have a molecular weight of 68 kDa, and its subunit molecular weight determined by SDS-PAGE was about 34 kDa, which indicated this enzyme was a dimer. Polycyclic nitroaromatic compounds were preferred substrates for this enzyme. The purified enzyme exhibited maximum activity at pH 7.5 and 40 °C. The addition of various chemicals such as reducing agents, metal ions, and chelating agents, had effects on enzyme activity. Mg2+, Ca2+, Sr2+, and 1% (w/v) Triton X-100 increased activity. However, Hg2+, Co2+, Ni 2+, Cu2+, and SDS reduced activity. The maximum reaction rate (Vmax) was 64 μM min-1 mg-1 enzyme and the apparent Michaelis-Menten constants (Km) for 4-nitro-1,8- naphthalic anhydride and NADH were 276 and 29 μM, respectively. Menadione, bimethylenebis, sodium benzoate, and antimycin A were inhibitors of the purified nitroreductase with apparent inhibition constants (Kis) of 20, 36, 44 and 80 μM, respectively.

A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent

Disseminated tumors lead to approximately 90% of cancer-associated deaths especially for hepatocellular carcinoma (HCC), indicating the imperative need of antimetastatic drugs and the ineffectiveness of current therapies. Recently polyamine derivatives have been identified as a promising prospect in dealing with metastatic tumors. Herein, a novel class of naphthalimide-polyamine conjugates 8a-8d, 13a-13c, 17 and 21 were synthesized and the mechanism was further determined. The polyamine conjugate 13b displayed remarkably elevated anti-tumor and anti-metastatic effects (76.01% and 75.02%) than the positive control amonafide (46.91% and 55.77%) at 5 mg/kg in vivo. The underlying molecular mechanism indicated that in addition to induce DNA damage by up-regulating p53 and γH2AX, 13b also targeted lysosome to modulate polyamine metabolism and function in a totally different way from that of amonafide. Furthermore, the HMGB1/p62/LC3II/LC3I and p53/SSAT/β-catenin pathways were mainly involved in the inhibition of 13b-induced HCC metastasis by targeting polyamine transporters (PTs) overexpressed in HCC. At last, 13b down-regulated the concentrations of Put, Spd and Spm by modulating polyamine metabolism key enzymes SSAT and PAO, which favored the suppression of fast growing tumor cells. Taken together, our study implies a promising strategy for naphthalimide conjugates to treat terminal cancer of HCC by targeting autophagy and tumor microenvironment with reduced toxicities and notable activities.

Distinguished Cys. Hcy And GSH naphthalimide fluorescent probe as well as preparation method and application thereof

The naphthalimide fluorescent probe can be used for distinguishing Cys, Hcy and GSH naphthalimide fluorescent probe as well as a preparation method and application thereof, and particularly relates to a fluorescence probe (Z1, Z2) for detecting a biological thiol through a urethane linker. The probe itself has blue fluorescence, emits yellow-green fluorescence with longer wavelength after the action of Cys and Hcy, and can realize distinguishing detection of Cys, Hcy and GSH. The fluorescent probe Z1, Z2 pairs Cys are high in action speed, strong in selectivity and high in sensitivity, can be used for detecting and imaging intracellular cysteine, and is simple in synthesis method, accessible in raw materials and easy to popularize.

A 4-aminonaphthalimide-based fluorescent traceable prodrug with excellent photoinduced cytotoxicity

A blue light activated anti-cancer prodrug, NST, was designed based on a photoactive 4-aminonaphthalimide derivative and an anticancer drug, 10-hydroxycamptothecin. NST was hard to be taken up by living cells and showed negligible dark cytotoxicity. The irradiation caused photocleavage of NST and resulted in high cytotoxicity.

Tetravalent platinum naphthalimide complex, preparation method and application thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a tetravalent platinum naphthalimide complex, a preparation method and application thereof. The tetravalent platinum naphthalimide complex has good anti-tumor activity, which is better than that of cis-platinum and oxaliplatin, and the tetravalent platinum naphthalimide complex has better stability than bivalent platinum like cis-platinum, carboplatin and oxaliplatin. According to the invention, the naphthalimide modified tetravalent platinum has good targeting performance on tumor cells, high selectivity on tumor cells is improved, and different from a classic divalent platinum drug, the complex provided by the invention regulates and controls subcellular organelles and cell nucleus functionsto reverse drug resistance by targeting a tumor high polyamine microenvironment, and relieves immunosuppression of T cells around tumors at the same time. The complex provided by the invention also solves the problems of poor solubility, tedious clinical compatibility, poor patient immunity in clinical application of chemotherapeutic drugs and the like of previous bivalent platinum antitumor drugs, and has good fat solubility and water solubility.