2348-79-0

Usage

Type

Fluorescent dye

Usage

Commonly used in biochemical and biomedical research

Absorption

Strong absorption in the ultraviolet and violet regions

Emission

Emits light in the blue region of the spectrum

Application

Labeling proteins, peptides, and other biomolecules in fluorescence studies

Reactivity

Reactive with amino groups

Labeling method

Can be used to label proteins and other molecules through amine-specific reactions

Analysis

Used in the analysis of peptides and amino acids by high-performance liquid chromatography (HPLC)

Visualization

Used as a fluorescent label in immunohistochemistry and immunoblotting techniques for visualizing proteins and other biomolecules.

Upstream product

• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 124-40-3 dimethyl amine 
• 91-20-3 naphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 111843-59-5 methyl (E)-4-dimethylhydrazono-2-butenoate 

Downstream Products

• 83889-95-6 2-(1-hydroxy-ethyl)-naphtho[2,3-b]furan-4,9-dione 
• 5350-26-5 2-chloro-3-(dimethylamino)naphthalene-1,4-dione 

Relevant academic research and scientific papers

Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity

To establish the structure-activity relationship of 5-hydroxy-1,4-naphthoquinones toward anticancer activity, a series of its derivatives were prepared and tested for the activity (IC50 in μM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among them 2 (IC50: 2.3; 2.0; 1.4 μM), 6 (IC50: 1.9; 2.2; 1.3 μM), 9 (IC50: 0.7; 1.7; 0.9 μM) and 10 (IC50:1.7; 1.0; 1.2 μM) showed moderate to excellent activity. Our perception toward the DNA substitution of alkoxy groups at the C2 position of these naphthoquinones for the anticancer activity led us to investigate their reactivity of substitution toward dimethylamine as a nucleophile. The ease of the substitution of alkoxy groups at the C2 position with dimethylamine is strongly accelerated by hydroxyl group at C5 position and is well correlated with the found anticancer activity results.

Concise synthesis of heterocycle-fused naphthoquinones by employing sonogashira coupling and tandem addition-elimination/intramolecular cyclization

A concise method for the synthesis of heterocycle-fused naphthoquinones such as naphtho[2,3-b]-furan-4,9-dione, 1H-benz[f]indole-4,9-dione, and naphtho[2,3-b]thiophene-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-

DIELS-ALDER REACTIONS OF A HYDRAZONOCROTONATE WITH BROMONAPHTHOQUINONES

An efficient and regiospecific synthesis of 4,6- and 4,9-disubstituted 5,10-benzoquinolinequinone derivatives was performed through a hetero Diels-Alder reaction between methyl (E)-4-dimethylhydrazono-2-butenoate (1) and 2- or 3-bromo-5-substituted naphthoquinones (2) and (3).According to the experimental conditions used, the corresponding dihydro or aromatic compounds were isolated as the major products.The regiochemistry of the cycloadditions is governed by the position of the bromine atom at C-2 or C-3 of the quinone.