60924-75-6

Basic information

• Product Name: 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione
• Synonyms: 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione;Asterriquinone A1;asterriquinone dimethyl ether
• CAS NO: 60924-75-6
• Molecular Formula: C34H34N2O4
• Molecular Weight: 534.64
• Mol File: 60924-75-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione(60924-75-6)
• EPA Substance Registry System: 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione(60924-75-6)

Safety Data

• Hazardous Substances Data: 60924-75-6(Hazardous Substances Data)

Usage

Description

2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione is a member of the asterriquinone class, specifically an asterriquinone with both hydroxy groups replaced by methyl groups. 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione features a unique structure that includes indole moieties and a cyclohexadiene core, which may contribute to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione is used as a pharmaceutical compound for its potential therapeutic properties. The indole and cyclohexadiene structures may provide opportunities for drug development, particularly in the areas of cancer treatment or other therapeutic applications where such structural features are known to be beneficial.
Used in Chemical Research:
In the field of chemical research, 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione can be utilized as a subject for studying the synthesis, properties, and reactions of complex organic molecules. Its unique structure may offer insights into new chemical pathways or mechanisms, contributing to the advancement of organic chemistry.
Used in Material Science:
2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione may also find applications in material science, where its structural features could be leveraged to develop new materials with specific properties. For instance, its indole and cyclohexadiene components might contribute to the creation of novel polymers, coatings, or other materials with unique characteristics.

Upstream product

• 186581-53-3 diazomethane 
• 60696-52-8 asterriquinone 
• 173348-61-3 asterriquinone monomethyl ether 
• 160786-85-6 2,5-bis<1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl>-3-acetoxy-6-hydroxy-2,5-cyclohexadiene-1,4-dione 
• 173348-60-2 Acetic acid 2,5-bis-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl ester 
• 173348-64-6 asterriquinone diacetate 
• 78723-19-0 asterriquinone D 
• 358-72-5 dimethylallyl diphosphate 
• 78708-37-9 asterriquinone B-3 

Downstream Products

• 60696-52-8 asterriquinone 
• 78860-36-3 2-[1-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-3,6-dihydroxy-5-(1H-indol-3-yl)-[1,4]benzoquinone 
• 78860-46-5 2,5-Dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methyl-but-2-enyl)-1H-indol-3-yl]-[1,4]benzoquinone 
• 78860-40-9 didemethylasterriquinone D 

Relevant articles and documents

AstPT catalyses both reverse N1- and regular C2 prenylation of a methylated bisindolyl benzoquinone

Prenylated bisindolyl benzoquinones exhibit interesting biological activities, such as antidiabetic or anti-HIV activities. A number of these compounds, including asterriquinones, have been isolated from Aspergillus terreus. In this study, we identified two putative genes by genome mining, ATEG-09980 and ATEG-00702, which share high sequence similarity with the known bisindolyl benzoquinone prenyltransferase TdiB from Aspergillus nidulans. The coding sequences were cloned and overexpressed in E. coli. The overproduced recombinant proteins were purified to near homogeneity and used for enzyme assays with asterriquinone D in the presence of dimethylallyl diphosphate. HPLC analysis showed that product formation was only detected in enzyme assays with EAU29429 encoded by ATEG-09980, not in those with EAU39348 encoded by ATEG-00702. Product isolation and structure elucidation by NMR and MS analyses led to identification of N1-reversely and C2-regularly monoprenylated derivatives, as well as N1′,N1′′reversely, N1′-reversely, C2′′-regularly diprenylated derivatives. This proved that EAU29429 functions as an asterriquinone prenyltransferase (AstPT) and indicated the involvement of EAU29429 rather than EAU39348 in the biosynthesis of methylated asterriquinones. Furthermore, incubation of monoprenylated enzyme products with AstPT resulted in the formation of the diprenylated derivatives. Copyright

Partial deacetylation of asterriquinone diacetate by aqueous sodium bicarbonate in pyridine

Asterriquinone (ARQ); 2,5 -bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3- yl]-3,6-dihydroxy-2,5-cyclohexadiene-1,4-dione and ARQ monoacetate are metabolites from mycelium of Aspergillus terreux IFO 6123. ARQ diacetate was convened into ARQ monoacetate by treatment with 5% aq. NaHCO3 in pyridine at 80°C for 5 min, and the yield was 93.4%. Similarly, by treatment with 5% aq. NaHCO3 in acetone at room temperature, 2,5-diacetoxy-p-xyloquinone and 2,5- diacetoxy-p-benzoquinone were convened into 2-acetoxy-5-hydroxy-p-xyloquinone (yield, 85.8%) and 2-acetoxy-5-hydroxy-p-benzoquinone (yield, 66.7%), respectively.