64505-67-5

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 106-40-1 4-bromo-aniline 
• 130-15-4 [1,4]naphthoquinone 
• 64-17-5 ethanol 
• 90-15-3 α-naphthol 
• 6628-97-3 2-(phenylamino)naphthoquinone 
• 1203-39-0 3-bromolawsone 
• 131940-35-7 2-(4-bromophenylamino)-3-bromonaphthalene-1,4-dione 

Downstream Products

• 62101-45-5 2-(4-bromophenylamino)-3-chloronaphthalene-1,4-dione 
• 131940-35-7 2-(4-bromophenylamino)-3-bromonaphthalene-1,4-dione 
• 128475-24-1 N-methyl-2-(4-bromophenyl)amino-1,4-naphthoquinone 
• 1445727-32-1 1-(4-bromophenyl)-1,2-dihydrobenzo[g]quinoline-5,10-dione 
• 1445727-18-3 2-((4-bromophenyl)(prop-2-ynyl)amino)naphthalene-1,4-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 106-40-1 4-bromo-aniline 

Relevant academic research and scientific papers

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

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.

Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones

Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y–M. Inhibition of this process by several anilino-, dianilino-, phenoxy-, and diphenoxy-1,4-naphthoquinones was investigated in order to find some correlation between structure, redox properties and biological activity.

Bodipy derivatives as organic triplet photosensitizers for aerobic photoorganocatalytic oxidative coupling of amines and photooxidation of dihydroxylnaphthalenes

We used iodo-Bodipy derivatives that show strong absorption of visible light and long-lived triplet excited states as organic catalysts for photoredox catalytic organic reactions. Conventionally most of the photocatalysts are based on the off-the-shelf compounds, usually showing weak absorption in the visible region and short triplet excited state lifetimes. Herein, the organic catalysts are used for two photocatalyzed reactions mediated by singlet oxygen ( 1O2), that is, the aerobic oxidative coupling of amines and the photooxidation of dihydroxylnaphthalenes, which is coupled to the subsequent addition of amines to the naphthoquinones, via C-H functionalization of 1,4-naphthoquinone, to produce N-aryl-2-amino-1,4-naphthoquinones (one-pot reaction), which are anticancer and antibiotic reagents. The photoreactions were substantially accelerated with these new iodo-Bodipy organic photocatalysts compared to that catalyzed with the conventional Ru(II)/Ir(III) complexes, which show weak absorption in the visible region and short-lived triplet excited states. Our results will inspire the design and application of new organic triplet photosensitizers that show strong absorption of visible light and long-lived triplet excited state and the application of these catalysts in photoredox catalytic organic reactions.

An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N- propargylaminonaphthoquinones

An expedient synthesis of a series of 1,2-dihydrobenzo[g]quinoline-5,10- diones in good yields has been accomplished via three-component one pot sequential reactions of 2-hydroxynaphthalene-1,4-dione, substituted anilines and propargyl as well as 3-ethylp

C-H functionalization of 1,4-naphthoquinone by oxidative coupling with anilines in the presence of a catalytic quantity of copper(II) acetate

The oxidative addition of anilines (2) with 1,4-naphthoquinone (3) to give N-aryl-2-amino-1,4-naphthoquinones (1) was found to be catalyzed by copper(II) acetate. In the absence of the catalyst, the reactions are slower and give lower yields with the formation of many colateral products. In the presence of 10 mol % hydrated copper(II) acetate, the reactions are generally more efficient in that they are cleaner, higher yielding, and faster.