42164-69-2

Usage

Uses

Used in Pharmaceutical Industry:
2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione is used as a pharmaceutical agent for its potential antibacterial, antiviral, and antitumor properties. It has shown promise in laboratory tests, indicating its potential use in the development of new medications to combat various diseases and infections.
Used in Traditional Medicine:
In traditional medicine, 2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione is used for its astringent and anti-inflammatory properties. These characteristics make it a valuable component in treatments for various ailments, particularly those involving inflammation and tissue repair.
Used in Agriculture:
2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione is used in agriculture for its allelopathic properties. It can be employed to control the growth of unwanted plants and weeds by releasing toxic chemicals into the soil, thus providing a natural and environmentally friendly method for managing plant competition.
Used in Cosmetics Industry:
Due to its astringent and anti-inflammatory properties, 2-[(3-methylbut-2-en-1-yl)oxy]naphthalene-1,4-dione can be used in the cosmetics industry for the development of skincare products. It may be incorporated into formulations to help reduce inflammation and tighten the skin, providing potential benefits for various cosmetic applications.

Upstream product

• 870-63-3 prenyl bromide 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 

Downstream Products

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 521-49-3 dunnione 

Relevant academic research and scientific papers

Synthesis and biological evaluation of lipophilic 1,4-naphthoquinone derivatives against human cancer cell lines

To examine the effect of hydrophobicity on the anticancer activity of 1,4-naphthoquinone derivatives, a series of compounds bearing a 2-O-alkyl-, 3-C-alkyl- or 2/3-N-morpholinoalkyl group were synthesized and evaluated for their anticancer activity against five human cancer cell lines in vitro. The cytotoxicity of these derivatives was assayed against HT-29, SW480, HepG2, MCF-7 and HL-60 cells by the MTT assay. Among them, 2-hydroxy-3-farnesyl-1,4-naphthoquinone (11a) was found to be the most cytotoxic against these cell lines. Our results showed that the effectiveness of compound 11a may be attributed to its suppression of the survival of HT-29. Secondly, in the Hoechst 33258 staining test, compound 11a-treated cells exhibited nuclear condensation typical of apoptosis. Additionally, cell cycle analysis by flow cytometry indicated that compound 11a arrested HT-29 cells in the S phase. Furthermore, cell death detected by Annexin V-FITC/propidium iodide staining showed that compound 11a efficiently induced apoptosis of HT-29 in a concentration-dependent manner. Taken together, compound 11a effectively inhibits colon cancer cell proliferation and may be a potent anticancer agent.

PHARMACEUTICAL COMPOSITION FOR TREATMENT AND PREVENTION OF RESTENOSIS

Provided is a pharmaceutical composition for the treatment and/or prevention of restenosis including (a) a therapeutically effective amount of a particular compound represented by Formula 1 and 2, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE

Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

A preparative synthesis of lapachol and related naphthoquinones

The lithium salt of 2-hydroxy-1,4-naphthoquinone was prepared in situ by addition of lithium hydride to the frozen solution of the quinone in dimethyl sulfoxide. As the solution thawed, the lithium quinone was slowly formed and was then alkylated with 3,3-dimethylallyl bromide. Lapachol was thus obtained in 40% yield. When treated with m-chloroperoxybenzoic acid it was converted into its epoxide, that was cyclized with boron trifluoride etherate to 3- hydroxy-β-lapachone in 67% overall yield. Esters of the latter were prepared by condensation with carboxylic acid derivatives using 1,1 '- carbonyldiimidazole and DBU as condensing agents.

β-Lapachone: Synthesis of Derivatives and Activities in Tumor Models

In order to find a 3,4-dihydro-2H-naphthopyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative , we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring.Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity.Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a.However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.

Synthesis of Naturally Occuring Naphthoquinones: Deoxylapachol, 2,3-Di-(3-methyl-but-2-enyl)-1,4-naphthoquinone, 2-Methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone and Lapachol

Deoxylapachol (I), 2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone (II), 2-methyl-3-(3-methyl-but-2-enyl)-1,4-naphthoquinone (III) and lapachol (IV) have been synthesised by the prenylation of 1,4-naphthoquinone (V) (for I and II), 2-methyl-1,4-naphthoquinone (VII) (for III) and 2-hydroxy-1,4-naphthoquinone (IX) (for IV) by prenyl bromide.