88051-30-3

Usage

General Description

NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN, 4-BROMO- is a chemical compound containing a naphthalene core with two dioxin rings, one of which is substituted with a bromine atom at the 4-position. This chemical is a member of the dioxin family, which are highly toxic and persistent environmental pollutants. Dioxins have been linked to a range of adverse health effects, including cancer, reproductive and developmental problems, immune system damage, and hormonal disruptions. The presence of a bromine atom in NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN, 4-BROMO- may have implications for its chemical reactivity and environmental behavior, potentially affecting its persistence and toxicity. Due to its hazardous nature, NAPHTHO[1,8-DE:4,5-D'E']BIS[1,3]DIOXIN, 4-BROMO- is subject to strict regulations and monitoring to minimize human and environmental exposure.

Upstream product

• 88051-28-9 naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine) 

Downstream Products

• 517-88-4 (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione 
• 517-89-5 shikonin 

Relevant academic research and scientific papers

Enantioselective Total Syntheses of (R)- A nd (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product

Both isomers of naphthotectone, an isoprenoid quinone from Verbenaceae Tectona grandis possessing interesting biological activities, were enantioselectively obtained by two different synthetic routes in which the carbon side-chain of the naphthoquinone core was introduced using either a Sonogashira or a Heck coupling reaction. In both cases, the naphthoquinone core of the final products was obtained by a late-stage anodic treatment. (R)-Naphthotectone was obtained in six steps from leuconaphthazarin with an overall yield of 38 % and an enantiomeric excess of 86 %. This compound was found to have the same absolute configuration as the natural product at its C-3′ stereogenic center. (S)-Naphthotectone was obtained in five steps from leuconaphthazarin with an overall yield of 36 % and an enantiomeric excess of 80 %. Naphthotectone was synthesized in both racemic and enantioenriched forms by two different synthetic strategies using Pd coupling reactions and anodic treatment as key steps. The stereochemistry of the natural product has been assigned.

Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study

The synthesis of 1,4-naphthoquinone derivatives is of great interest since these compounds exhibit strong activity as antimalarial, antibacterial, antifungal and anticancer agents. A series of 50 naphthoquinone derivatives was synthesized and evaluated for antibacterial and antifungal activity against Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Candida krusei, Candida parapsilosis and Cryptococcus neoformans using the broth microdilution method. The Candida species were the most susceptible microorganisms. Halogen derivatives of 1,4-naphthoquinone presented strong activity, e.g., 2-bromo-5-hydroxy-1,4-naphthoquinone, which exhibited inhibition at an MIC of 16?μg/mL in S. aureus, and 2-chloro-5,8-dihydroxy-1,4-naphthoquinone, with an MIC of 2?μg/mL in C. krusei. These compounds showed higher activity against fungi, but the antibacterial activities were very low. The study of structure–activity relationships is very important in the search for new antimicrobial drugs due to the limited therapeutic arsenal.

A convenient synthesis of 2-formyl-1,8:4,5-bis(methylenedioxy) naphthalene

2,3-Dihydronaphazarin was prepared from 1,4-dimethoxybenzene and dichloromaleic anhydride. Reaction with bromochloromethane gave 1,8:4,5-bis(methylenedioxy)naphthalene which with NBS, gave 2-bromo-1,8:4,5-bis- (methylenedioxy)naphthalene. Reaction of the Grignard derivative with DMF afforded 2-formyl-1,8:4,5-bis(methylenedioxy)naphthalene. This method had several advantages compared with the reported synthesis, including fewer steps, milder condition and higher yields.

Concise and efficient total syntheses of alkannin and shikonin

Two enantiomic natural products with wound-healing properties, alkannin (1) and shikonin (2), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8-dihydroxy-1,4-naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction.

Naphtho-1,3-dioxines

Treatment of 1,8-Dihydroxy-naphthaline with bromochloromethane/K2CO3 in DMF gives Naphtho-1,3-dioxine (1a) in good yield.The bromo (1b) and nitro compound (1c) can be obtained free of isomerics by electrophilic substitution of 1a.Bromolithium exchange of 1b leads to a lithium organic compound, which possibles the synthesis of alkyl-, olefinic-, and carboxylic derivatives of the substrate 1a.In a similar way the treatment of 2,3-dihydroxynaphthazarin with chlorobromomethane/K2CO3 gives the naphtho-bis-1,3-dioxine (3a).The substrate 3a can besubjected to electrophilic aromatic substitutions. - Key words: 6-Brom-naphtho-1,3-dioxine, 6-Nitro-naphtho-1,3-dioxine, 4-Methyl-naphthobis-1,3-dioxine-9-carboxylic Acid