6628-97-3

Usage

Abbreviation

ANQ

Classification

Naphthoquinone derivative

Primary Use

Redox mediator and electron transfer agent

Applications

Electrochemical sensing
Analytical chemistry

Properties

Antioxidant: Exhibits antioxidant properties
Anti-inflammatory: Demonstrates anti-inflammatory properties

Significance

Valuable tool in bioanalytical chemistry
Significant in materials science
Relevant in medicinal chemistry

Potential Applications

Development of novel drugs
Design of drug delivery systems

Reasons for Importance

Unique chemical structure
Diverse biological activities

InChI:InChI=1/C16H11NO2/c18-15-10-14(17-11-6-2-1-3-7-11)16(19)13-9-5-4-8-12(13)15/h1-10,17H

Upstream product

• 74-96-4 ethyl bromide 
• 64-17-5 ethanol 
• 27828-56-4 4-(phenylamino)naphthalene-1,2-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 542-14-3 aniline acetate 
• 506-96-7 Acetyl bromide 
• 21720-68-3 2-(phenylamino)-4-(phenylimino)-1(4H)-naphthalenone 
• 108-24-7 acetic anhydride 
• 98-88-4 benzoyl chloride 
• 75-03-6 ethyl iodide 
• 64-19-7 acetic acid 
• 75139-96-7 2-Methoxy-naphthochinon-1.4-4-anilid 
• 24308-76-7 phenyl-(4-phenylazo-[1]naphthyl)-amine 
• 62-53-3 aniline 

Downstream Products

• 134045-53-7 1,2,3,4,5,10-Hexahydro-3-methyl-5,10-dioxo-1-phenyl-benzo-3-chinazolinium-perchlorat 
• 134045-56-0 3-Bnezyl-1,2,3,4,5,10-hexahydro-5,10-dioxo-1-phenyl-benzo-3-chinazolinium-perchlorat 
• 1090-16-0 2-chloro-3-(phenylamino)naphthalene-1,4-dione 
• 571-60-8 1,4-Dihydroxynaphthalene 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 62-53-3 aniline 
• 845729-99-9 2-anilino-1,4-naphthoquinone-3-sulphonyl chloride 
• 868562-63-4 C₃₂H₂₀N₂O₄S₂ 
• 1445727-29-6 2-(phenyl(prop-2-ynyl)amino)naphthalene-1,4-dione 
• 1445727-43-4 1-phenyl-1,2-dihydrobenzo[g]quinoline-5,10-dione 

Relevant academic research and scientific papers

Copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes

A copper-catalyzed one-pot amine-alkylation of quinones with amines and alkanes in the presence of di-tert-butyl peroxide (DTBP) was developedviaa radical reaction process. Various alkanes and aromatic or aliphatic amines with diverse structures and electronic properties are suitable substrates, and the chirality of amines can be maintained for the transformation. This method has high step and atom economy for straightforward access to aminated and alkylated quinones from readily available starting materials.

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

Computer-aided design of 1,4-naphthoquinone-based inhibitors targeting cruzain and rhodesain cysteine proteases

Chagas disease and Human African Trypanosomiasis (HAT) are caused by Trypanosoma cruzi and T. brucei parasites, respectively. Cruzain (CRZ) and Rhodesain (RhD) are cysteine proteases that share 70% of identity and play vital functions in these parasites.

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.

AMINO-QUINONE ANTIPOLYMERANTS AND METHODS OF USING

Described are methods and composition for inhibiting polymerization of a monomer (e.g., styrene) composition using an aminated quinone antipolymerant, such as an aminated benzoquinone or aminated naphthoquinone antipolymerant having one or more secondary or tertiary amine group(s). The aminated quinone antipolymerant can be used with little or no nitroxyl group containing antipolymerant yet still provide excellent antipolymerant activity in a monomer-containing composition.

IDO inhibitor, preparation method and applications thereof

The invention relates to an IDO inhibitor, a preparation method and applications thereof, and belongs to the technical field of medicinal chemistry. The IDO inhibitor with the characteristics of a structure represented by a general formula I or the pharma

Synthesis of carbazoloquinone derivatives and their antileukemic activity via modulating cellular reactive oxygen species

Carbazoloquinone alkaloids are of great interest as privileged structures for anticancer drug molecules. The purpose of this study was to investigate the structure-activity relationships of carbazoloquinone derivatives as anticancer agents. A series of ca

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.