1146-72-1

Usage

Uses

Used in Pharmaceutical Industry:
4-acetyl-1,8-naphthalic anhydride is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drug compounds.
Used in Dye and Pigment Industry:
4-acetyl-1,8-naphthalic anhydride is used as a key component in the production of dyes and pigments, where its chemical properties allow for the creation of a wide range of colorants.
Used in Fluorescent Dye Production:
4-acetyl-1,8-naphthalic anhydride is used as a precursor in the production of fluorescent dyes, taking advantage of its potential to emit light upon exposure to certain wavelengths.
Used in Organic Synthesis as a Reagent:
In the field of organic synthesis, 4-acetyl-1,8-naphthalic anhydride serves as a reagent, facilitating various chemical reactions that are crucial for the synthesis of complex organic molecules.
Used in Thiol Detection as a Fluorescent Probe:
4-acetyl-1,8-naphthalic anhydride is studied for its potential use as a fluorescent probe for the detection of thiols, highlighting its possible application in analytical chemistry and biochemistry.
Used in Anti-Cancer Research:
4-acetyl-1,8-naphthalic anhydride is being investigated for its potential as an anti-cancer agent, with research focusing on its ability to target and affect cancer cells.

InChI:InChI=1/C14H8O4/c1-7(15)8-5-6-11-12-9(8)3-2-4-10(12)13(16)18-14(11)17/h2-6H,1H3

Upstream product

• 10047-18-4 5-acetylacenaphthene 
• 859984-27-3 1-(5,6-dihydro-4H-phenalen-1-yl)-ethanone 
• 64-19-7 acetic acid 
• 479-58-3 perinaphthane 
• 83-32-9 acenaphthene 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel aromatic imide-polyamine conjugates

Three types of conjugates in which aromatic imide scaffolds were coupled to diverse amine/polyamine motifs were synthesized, and their antitumor activities were evaluated in vitro and in vivo. Results showed that the conjugate 11e of 1,8-naphthilimide with spermine had pronounced effects on inhibiting tumor cell proliferation and inducing tumor cell apoptosis via ROS-mediated mitochondrial pathway. The in vivo assays on three H22 tumor transplant models revealed that compound 11e exerted potent ability in preventing lung cancer metastasis and extending lifespan. Furthermore, the efficacy of 11e in inhibiting tumor growth and improving body weight index were better than that of positive control, amonafide. Our study demonstrates that compound 11e is a valuable lead compound for further investigation.

Naphthalimide trifluoroacetyl acetonate: A hydrazine-selective chemodosimetric sensor

The trifluoroacetyl acetonate naphthalimide derivative 1 has been synthesized in good yield. In acetonitrile solution, compound 1 reacts selectively with hydrazine (NH2NH2) to give a five-membered ring. This leads to OFF-ON fluorescence with a maximum intensity at 501 nm as well as easily discernible color changes. Based on a readily discernible and reproducible 3.9% change in overall fluorescence intensity, the limit of detection for 1 is 3.2 ppb (0.1 μM), which is below the accepted limit for hydrazine set by the U.S. Environmental Protection Agency (EPA). Compound 1 is selective for hydrazine over other amines, including NH 4OH, NH2OH, ethylenediamine, methylamine, n-butylamine, piperazine, dimethylamine, triethylamine, pyridine, and is not perturbed by environmentally abundant metal ions. When supported on glass-backed silica gel TLC plates, compound 1 acts as a fluorimetric and colorimetric probe for hydrazine vapor at a partial pressure of 9.0 mm Hg, with selectivity over other potentially interfering volatile analytes, including ammonia, methylamine, n-butylamine, formaldehyde, acetaldehyde, H2O2, HCl, and CO2 being observed. Probe 1 can also be used for the detection of hydrazine in HeLa cells and does so without appreciable interference from other biologically abundant amines and metal ions. The Royal Society of Chemistry 2013.

Aromatic heterocyclic modified naphthalimide derivative as well as preparation method and application thereof

The invention discloses an aromatic heterocyclic modified naphthalimide derivative, which has a structural general formula as shown in I, a skeleton is novel, the derivative has high efficiency and low toxicity, and good inhibitory activity on tumor cells. The invention also discloses a preparation method of the compound, which comprises the following steps: by using naphthalimide as a raw material, respectively introducing active groups imidazopyridine and aminothiazole into the parent naphthalene ring to synthesize a new aromatic heterocyclic modified naphthalimide pharmacophore, modifying with a polyamine chain, designing and synthesizing a series of naphthalimide derivatives modified with imidazopyridine and aminothiazole. The compound retains the antitumor activity of naphthalimide and also has the characteristics of imidazopyridine and aminothiazole, the biological activity of original molecules is improved, and the antitumor activity of target molecules is improved. The invention also provides an application of the compound in preparation of antitumor drugs, and the compound shows good development potential.

Combining viscosity-restricted intramolecular motion and mitochondrial targeting leads to selective tumor visualization

We report a novel fluorescent molecular conjugate, V-M1, enabling an accurate visualization of tumor tissues. The emission wavelength of V-M1 exceeds 650 nm, which is well within the near-infrared therapeutic window. Tumor accumulation of this cationic dye allows the visualization of cancerous cells as a function of mitochondrial viscosity.

Naphthalimide Scaffold Provides Versatile Platform for Selective Thiol Sensing and Protein Labeling

Reversible thiol modifications are fundamental of cellular redox regulation. Specific thiol detection, including thiol sensing and protein thiols labeling, is critical to study such modifications. We reported the discovery of 4-methylsulfonyl-N-n-butyl-1,8-naphthalimide (MSBN), a highly selective fluorogenic probe for thiols based on the 1,8-naphthalimide scaffold. Thiols react with MSBN nearly quantitatively via nucleophilic aromatic substitution to replace the methylsulfonyl group and restore the quenched fluorescence (>100-fold increase). MSBN was employed to selectively image thiols in live cells and specifically label protein thiols with a turn-on signal to determine diverse reversible protein thiol modifications. In addition, we introduced a bulky group into the MSBN as a mass tag to create a probe MSBN-TPP, which readily discriminates the reduced thioredoxin from the oxidized one. The specific reaction of MSBN with thiols and the easy manipulation of the naphthalimide unit enable MSBN a versatile scaffold in developing novel probes for thiol-based protein bioconjugation and studying various thiol modifications.