35135-38-7

Usage

Uses

Used in Organic Synthesis:
1,4-Naphthalenedione, 2-hydroxy-3-iodois used as a key intermediate in the synthesis of various organic compounds, contributing to the formation of complex molecules and enhancing the diversity of chemical products.
Used in Pharmaceutical Industry:
1,4-Naphthalenedione, 2-hydroxy-3-iodoserves as a pharmaceutical intermediate, playing a crucial role in the development of new drugs and medicines. Its unique structure allows for the creation of novel therapeutic agents with potential applications in various medical fields.
Used in Dye and Pigment Manufacturing:
In the dye and pigment industry, 1,4-Naphthalenedione, 2-hydroxy-3-iodois utilized in the production of dyes and pigments, providing color and stability to various products, including textiles, plastics, and paints.
Used in Material Science:
1,4-Naphthalenedione, 2-hydroxy-3-iodohas potential applications in material science due to its unique chemical properties, which can be leveraged to develop new materials with enhanced properties, such as improved conductivity, stability, or reactivity.
Used in Nanochemistry:
1,4-Naphthalenedione, 2-hydroxy-3-iodo-'s structure and properties make it a promising candidate for nanochemistry applications, where it can be used to create nanoscale materials with specific functions, such as drug delivery systems, sensors, or catalysts.

Upstream product

• 117560-06-2 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide 
• 571166-63-7 Z,E-3-iodo-4-hydroxy-1[(2-phenylethyl)imino]-2-naphthalenone 
• 106-49-0 p-toluidine 
• 572874-62-5 3-iodo-4-hydroxy-1,2-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 74-88-4 methyl iodide 

Downstream Products

• 6628-97-3 2-(phenylamino)naphthoquinone 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 62452-63-5 2-phenylnaphtho[2,3-b]furan-4,9-dione 
• 655-86-7 2,3-diaminephenazine 
• 10409-20-8 2-(4-chlorophenyl)-3-hydroxynaphthalene-1,4-dione 
• 1150-59-0 2-hydroxy-3-phenyl-1,4-naphthoquinone 

Relevant academic research and scientific papers

Lawsone, Juglone, and β-Lapachone Derivatives with Enhanced Mitochondrial-Based Toxicity

Naphthoquinones are among the most active natural products obtained from plants and microorganisms. Naphthoquinones exert their biological activities through pleiotropic mechanisms that include reactivity against cell nucleophiles, generation of reactive oxygen species (ROS), and inhibition of proteins. Here, we report a mechanistic antiproliferative study performed in the yeast Saccharomyces cerevisiae for several derivatives of three important natural naphthoquinones: lawsone, juglone, and β-lapachone. We have found that (i) the free hydroxyl group of lawsone and juglone modulates toxicity; (ii) lawsone and juglone derivatives differ in their mechanisms of action, with ROS generation being more important for the former; and (iii) a subset of derivatives possess the capability to disrupt mitochondrial function, with β-lapachones being the most potent compounds in this respect. In addition, we have cross-compared yeast results with antibacterial and antitumor activities. We discuss the relationship between the mechanistic findings, the antiproliferative activities, and the physicochemical properties of the naphthoquinones.

Novel trifluoroethyliodonium salts from cyclic enaminones and their thermal decomposition

Upon reaction of 1-[hydroxy(tosyloxy)iodo]-2,2,2-trifluoroethane with cyclic enaminones, stable iodonium tosylates are obtained. Their mild thermolysis provides iodoenaminones and 2,2,2-trifluoroethyl tosylate.

METHOD FOR PRODUCING 2-ALKYLCARBONYLNAPHTHO[2,3-b]FURAN-4,9-DIONE-RELATED SUBSTANCE, AND SAID RELATED SUBSTANCE

Provided is a method for producing a 2-alkylcarbonylnaphtho[2,3-b]furan-4,9-dione-related substance, which is suitable for the production on an industrial scale. The present invention provides: a method for producing an intermediate for the production of

Pd(II)-Catalyzed Synthesis of Alkylidene Phthalides via a Decarbonylative Annulation Reaction

An unprecedented Pd(II)-catalyzed decarbonylative C-H/C-C activation and annulation reaction, which proceeds via intramolecular cyclization, is reported. This reaction of hydroxynaphthoquinones with disubstituted alkynes provides good yields of substituted alkylidene phthalides, which are the key intermediates for the synthesis of bioactive natural products.

1,4-Naphthoquinones potently inhibiting P2X7 receptor activity

P2X7 receptor (P2X7R) is an ATP-gated ion-channel with potential therapeutic applications. In this study, we prepared and searched a series of 1,4-naphthoquinones derivatives to evaluate their antagonistic effect on both human and murine P2X7 receptors. W

Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

Styrenes were coupled with 3-iodolawsone in PEG-400 at 90 °C, leading stereoselectively to (E)-stilbene-quinone hybrids through Heck reactions. The best reaction conditions were found to be the use of NaOH (3 equiv) and 10 mol% of palladium acetate at 90 °C for 15 minutes. The chemical yields of the Heck reactions using styrenes with electron-withdrawing groups (65-98%) were greater than styrenes bearing electron-donating groups (7-32%) on the aromatic ring. In particular, the chemical yields of Heck reactions involving nitrostyrenes were the best ones observed.

Suzuki-Miyaura coupling between 3-iodolawsone and arylboronic acids. Synthesis of lapachol analogues with antineoplastic and antileishmanial activities

A series of 2-hydroxy-3-arylnaphthalene-1,4-diones (3-aryllawsones) were synthesized by Suzuki-Miyaura cross coupling reaction of 3-iodolawsone with arylboronic acids/esters. The hydroxylated resulting products were transformed into their corresponding N,N-diethyl carbamates. The antineoplastic and antileishmanial activities of the compounds were evaluated and compared with lapachol and its carbamate, providing promising results.

Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones-green palladium-catalysed Suzuki cross coupling

Quinones are important scaffolds that are present in a variety of natural products or synthetic bioactive molecules. Arylation is an important strategy for accomplishing structural modifications, leading to new potential candidates for use as drugs. In the present work, palladium-catalysed, ligandless and phosphine-free Suzuki coupling reactions between 2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated. The Osiris and Molinspiration Cheminformatics programs, utilizing in silico analyses, imply that these naphthoquinones are candidates for use as drugs which was reinforced by the outcomes of the in vitro antifungal and trypanocidal activity tests. Our in vitro data indicated a MIC value of 8 μg mL-1 against Candida albicans ATCC 24433 strains, and an EC50 of 0.67 μM with respect to trypanocidal activity against Trypanosoma cruzi epimastigote strains (Y).

Oxidative iodination of carbonyl compounds using ammonium iodide and oxone

A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.

Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase.