33440-64-1

Usage

Uses

Used in Traditional Medicine:
BI-LAWSONE is used as a therapeutic agent in traditional medicine for its anti-inflammatory, anti-microbial, and anti-cancer properties, offering a natural alternative for various health conditions.
Used in Pharmaceutical Applications:
In the pharmaceutical industry, BI-LAWSONE is used as a potential drug candidate for its anti-inflammatory, anti-microbial, and anti-cancer properties, with ongoing research to explore its full potential in treating various diseases.
Used in Cosmetics:
BI-LAWSONE is used as a natural dye in hair and skin products, providing a safe and effective coloring solution. Its anti-inflammatory properties also make it a popular ingredient in topical skincare products, promoting skin health and reducing inflammation.
Used in Natural Dyeing:
In the textile industry, BI-LAWSONE is used as a natural dye for fabrics, offering a sustainable and eco-friendly alternative to synthetic dyes. Its vibrant color and traditional use in henna make it a popular choice for temporary body art and decorative purposes.

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 3408-13-7 2,2'-binaphthoquinone 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 405264-19-9 3'-chloro-3-hydroxy-2,2'-binaphthalenyl-1,4,1',4'-tetraone 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 

Downstream Products

• 88-99-3 benzene-1,2-dicarboxylic acid 
• 26171-90-4 Dinaphtho<2,3-b;2',3'-d>furan-5,13;7,12-dichinon 
• 75083-40-8 Dinaphtho<2,3-b;1',2'-d>furan-5,13;11,12-dichinon 

Relevant academic research and scientific papers

Photoinduced Molecular Transformations. Part 145. Regioselective Photoaddition of 2-Hydroxyphenanthrene-1,4-dione with Electron-rich Alkenes and Phenylacetylene: New One-step Synthesis of 9,10-Dihydrophenanthrofuran-7,11-diones and 2-Phenylphenanthrofuran-7,11-dione

The irradiation of 2-hydroxyphenanthrene-1,4-dione and various electron-rich alkenes such as ethyl vinyl ether, isobutene, 1-methoxycyclohexene and 3,4-dihydro-2H-pyran in acetone with Pyrex-filtered light gave 9,10-dihydrophenanthrofuran-7,11-diones arising from regioselective photoaddition in 25 - 50percent yields.A photoadduct, 9-phenylphenanthrofuran-7,11-dione, can be similarly formed in low yield when 2-hydroxyphenanthrene-1,4-dione and phenylacetylene in acetone are irradiated with Pyrex-filtered light.In contrast, the irradiation of 2-hydroxyphenanthrene-1,4-dione and alkenes such as methyl acrylate, acrylonitrile, cyclohexene, isopropenyl acetate, propenyl acetate, vinyl acetate, 1-phenylprop-1-yne or trimethylsilylacetylene in acetone gave only a dimer in 42-52percent yields, no photoadducts being formed.

Vanadium (V) in perchloric acid: A novel use of the reagent for dimerisation of some naphtalene derivatives

Oxidative dimerisation of 2-naphthol and its methyl ether into the respective 1, 1'-dimers was achieved in good yield and excellent purity through a one-step method using ammonium metavanadate and dilute perchloric acid. 1-Naphthol gave a mixture of isomeric dimers, although its methyl ether was converted almost quantitatively into the corresponding 4, 4'-dimer. This reagent could also dimerise 2-hydroxyl-1, 4-naphthoquinone, a natural product.

Advance of Seriniquinone Analogues as Melanoma Agents

Seriniquinone, a marine natural product, displayed potent cytotoxicity and selectivity against melanoma cancer cells. This selectivity, combined with a novel mode of action (MOA), prompted studies to translate a pharmacologically relevant lead. Herein, we report on structure-activity relationships (SARs), and provide a strategy to prepare analogues that retain activity and offer an improved water solubility and isomeric purity. From intermediates made on a gram-scale, derivatives were prepared and evaluated for their antiproliferation activity and melanoma selectivity. Overall these studies provide methods to install side chain motifs that demonstrate a common, and yet unique, biological profile.

Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis-Naphthoquinones

An efficient annulation involving pyrone addition to a quinone and Dieckmann condensation was developed for rapid assembly of a γ-naphthopyrone monomeric precursor to the bis-naphthoquinone natural product aurofusarin. Dimerization was achieved through Pd

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG). Our work highlights the significant potential of naturally occurring angular-series naphthoquinones as antileukemic agents.

SERINIQUINONES, MELANOMA-SPECIFIC ANTICANCER AGENTS

Accordingly, there are provided, inter alia, derivatives of seriniquinone and methods useful for the treatment of cancer, and in particular treatment of melanoma and prostate cancer.