57182-49-7

Usage

Molecular structure

The compound has a naphthalene-1,4-dione backbone with an attached 4-methylphenylamino group.

Usage

It is commonly used in the synthesis of dyes and pigments, as well as in the production of optical brighteners and fluorescent dyes.

Industrial applications

It has potential uses in organic electronic devices and as a sensitizer in dye-sensitized solar cells.

Biological activities

It has been studied for its potential anti-cancer and anti-inflammatory properties.

Wide range of applications

The compound has a variety of uses and potential applications in different industries.

Upstream product

• 7473-18-9 2-ethoxy-1,4-naphthoquinone 
• 106-49-0 p-toluidine 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 64-19-7 acetic acid 
• 110-86-1 pyridine 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 64-17-5 ethanol 
• 130-15-4 [1,4]naphthoquinone 
• 2066-93-5 3,4-dioxo-3,4-dihydro-naphthalene-1-sulfonic acid 
• 69085-39-8 4-((4-methylphenyl)amino)naphthalene-1,2-dione 
• 91-20-3 naphthalene 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 2065-37-4 2-bromo-1,4-naphthoquinone 

Relevant academic research and scientific papers

t-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines

The transition-metal free amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines, such as various (hetero)aromatic amine and aliphatic aminevia t-BuOK-mediated oxidative coupling at room temperature has been developed. This react

Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones

A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and N-allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature a

Exploration of Benzo[b]carbazole-6,11-diones as anticancer agents: Synthesis and studies of hTopoIIα inhibition and apoptotic effects

Two series of (hetero)arylamino-naphthoquinones and benzo-fused carbazolequinones were considered for study with the rationale that related structural motifs are present in numerous drugs, clinical trial agents, natural products and hTopoIIα inhibitors. Total 42 compounds were synthesized by reactions including dehydrogenative C–N and Pd-catalyzed C–C bond forming transformations. These compounds were screened against numerous cancer cells including highly metastatic one (MCF-7, MDA-MB-231, H-357 and HEK293T), and normal cells (MCF 10A). Some of the active compounds were evaluated for clonogenic cell survival and apoptotic effects in cancer cells (DAPI nuclear staining, Comet assay, Annexin-V-FITC/PI dual staining, flow cytometry, and western blot analysis with relevant proteins). All compounds were tested for hTopoIIα inhibitory activity. The investigated series compounds showed important properties like significant apoptotic antiproliferation in cancer cells with cell cycle arrest at S-phase and downregulation of NF- κβ signaling cascade, relatively less cytotoxicity to normal cells, and hTopoIIα inhibition with more efficiency compared to an anticancer drug etoposide.

It takes two to tango: synthesis of cytotoxic quinones containing two redox active centers with potential antitumor activity

We report the synthesis of 47 new quinone-based derivativesviaclick chemistry and their subsequent evaluation against cancer cell lines and the control L929 murine fibroblast cell line. These compounds combine two redox centers, such as anortho-quinone/para-quinone or quinones/selenium with the 1,2,3-triazole nucleus. Several of these compounds present IC50values below 0.5 μM in cancer cell lines with significantly lower cytotoxicity in the control cell line L929 and good selectivity index. Hence, our study confirms the use of a complete and very diverse range of quinone compounds with potential application against certain cancer cell lines.

Fluorescent 1,4-Naphthoquinones to Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains

Recent clinical approvals of brain imaging radiotracers targeting amyloid-β provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4-naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-β aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-β aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-β plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-β imaging agents for early stage Alzheimer's.

A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water

A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.

Method for synthesizing 2-substituted amino-1,4-naphthoquinone derivative

The invention discloses a method for synthesizing a 2-substituted amino-1,4-naphthoquinone derivative. The method comprises the following steps: mixing a nitro compound, 2-substituted 1,4-naphthoquinone, a catalyst, a metal and a solvent uniformly at 20-100 DEG C; adding an H source, stirring the components for reaction for 1-24h; performing a reduction-addition reaction between the nitro compoundand the 2-substituted 1,4-naphthoquinone; after the reaction, adding water to the reaction system for dilution; performing filtering; extracting filtrate with ethyl acetate; after organic phases arecombined, washing the mixture with saturated saline solution and drying the mixture with anhydrous sodium sulfate sequentially; subsequently, performing filtering, and performing vacuum concentrationto remove a solvent; and packing solids into a column, and performing separation through column chromatography (a ratio of petroleum ether to ethyl acetate is 5:1) to obtain red solids. Compared withan existing synthesis method, the synthesis method provided by the invention has a wide range of raw materials and the raw materials are easy to obtain; compared with amine compounds, nitro compoundshave better stability; and the synthesis method provided by the invention is simple to operate and mild in reaction condition.

Isomerization of 4-arylamino-1,2-naphthoquinones to 2-arylamino-1,4-naphthoquinones

4-Arylamino-1,2-naphthoquinones isomerize into 2-arylamino-1,4-naphthoquinones upon refluxing in acetic acid. The isomerization follows two routes via intermediate 2-hydroxy-1,4-naphthoquinone and 2-arylamino-1,4-naphthoquinone 4-N-arylimines.

Synthesis of novel substituted methoxybenzo[2,3-b]carbazole derivatives via C-H functionalization. Experimental and theoretical characterization of their photophysical properties

The novel, highly blue, fluorescent N-methyl-6,11-dimethoxybenzo[2,3-b]carbazole derivatives were prepared by oxidative coupling of anilines with naphthoquinone followed by palladium catalyzed oxidative [Formula presented] functionalization and a one pot

INHIBITORS OF THE MITF MOLECULAR PATHWAY

Provided herein are compounds of the formula (IV) as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful as MITF inhibitors, MITF pathway inhibitors and for the treatment of cancer.