1146-72-1

Basic information

• Product Name: 4-ACETYL-1,8-NAPHTHALIC ANHYDRIDE
• Synonyms: 6-Acetyl-benzo[de]isochromene-1,3-dione
• CAS NO: 1146-72-1
• Molecular Formula: C₁₄H₈O₄
• Molecular Weight: 240.21
• Product Categories: Phthalic Acids, Esters and Derivatives
• Mol File: 1146-72-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 499.3°C at 760 mmHg
• Flash Point: 227.8°C
• Appearance: /
• Density: 1.428g/cm³
• Vapor Pressure: 4.19E-10mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 4-ACETYL-1,8-NAPHTHALIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETYL-1,8-NAPHTHALIC ANHYDRIDE(1146-72-1)
• EPA Substance Registry System: 4-ACETYL-1,8-NAPHTHALIC ANHYDRIDE(1146-72-1)

Safety Data

• Hazardous Substances Data: 1146-72-1(Hazardous Substances Data)

Usage

General Description

4-acetyl-1,8-naphthalic anhydride is a chemical compound with the molecular formula C14H12O3. It is a white to off-white solid that is insoluble in water but soluble in organic solvents. 4-acetyl-1,8-naphthalic anhydride is often used as an intermediate in the synthesis of various pharmaceuticals, dyes, and pigments. It is also used in the production of fluorescent dyes and as a reagent in organic synthesis. Additionally, 4-acetyl-1,8-naphthalic anhydride has been studied for its potential as a fluorescent probe for the detection of thiols and as a potential anti-cancer agent. However, it is important to handle this compound with caution, as it can cause skin and eye irritation, and it may pose environmental hazards if not properly handled and disposed of.

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

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Relevant articles and documents

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.

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.

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.