78723-19-0

Basic information

• Product Name: 2,5-Bis(1H-indol-3-yl)-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione
• Synonyms: 2,5-Bis(1H-indol-3-yl)-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione;Asterriquinone D
• CAS NO: 78723-19-0
• Molecular Weight: 0
• Mol File: 78723-19-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-Bis(1H-indol-3-yl)-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Bis(1H-indol-3-yl)-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione(78723-19-0)
• EPA Substance Registry System: 2,5-Bis(1H-indol-3-yl)-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione(78723-19-0)

Safety Data

• Hazardous Substances Data: 78723-19-0(Hazardous Substances Data)

Upstream product

• 78279-83-1 7-(1H-Indol-3-yl)-5,8-dimethoxy-9a,10-dihydro-9-oxa-10-aza-indeno[1,2-a]indene-4b,6-diol 
• 78279-84-2 C₂₄H₂₀N₂O₆ 
• 213831-78-8 acetic acid 4-hydroxy-2,5-bis-(1H-indol-3-yl)-3,6-dioxo-cyclohexa-1,4-dienyl ester 
• 67-56-1 methanol 
• 1078057-85-8 3,6-dichloro-2,5-bis(3-indolyl)-1,4-benzoquinone 
• 213831-71-1 acetic acid 4-acetoxy-2,5-bis-(1H-indol-3-yl)-3,6-dioxo-cyclohexa-1,4-dienyl ester 
• 213831-84-6 acetic acid 2,5-bis-(1H-indol-3-yl)-4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl ester 
• 78860-40-9 didemethylasterriquinone D 
• 186581-53-3 diazomethane 
• 213831-94-8 2-hydroxy-3,6-bis-(1H-indol-3-yl)-5-methoxy-[1,4]benzoquinone 

Downstream Products

• 78860-40-9 didemethylasterriquinone D 
• 60924-75-6 asterriquinone dimethyl ether 
• 78708-37-9 asterriquinone B-3 

Relevant articles and documents

A facile synthesis of asterriquinone D

(Chemical Equation Presented) Asterriquinone D was easily synthesized in three steps from 2,5-dichloro-1,4-benzoquinone. The reaction of benzoquinone with indole in the presence of Pd(OAc)2, followed by oxidation with cerium (IV) ammonium nitrate (CAN) produced 3,6-dichloro-2,5-bis (3-indolyl)-1,4-benzoquinone. The methoxylation of the dichloride with NaOH in CH3OH afforded asterriquinone D.

Preparation and structure-activity relationships of novel asterriquinone derivatives

Asterriquinone (ARQ, la) is an antitumor metabolite of Aspergillus terreus IFO 6123. To gain insight into the structure-activity relationships of ARQ, a series of chemically modified derivatives (1 - 6), the ARQ analogues (b - e) and the 2,5-dihydroxy-p-benzoquinone analogues (f - h), were prepared, and cytotoxic activity against mouse leukemia P388 cells investigated. Results indicated that: 1) at least one hydroxy group or acetoxy group in the p-benzoquinone moiety is important to exhibit cytotoxicity; 2) in the p-benzoquinone moiety, a single methoxy group and/or one acetoxy group substitution showed more potent cytotoxicity than when two hydroxy groups are substituted (1); 3) the indole ring is important for the cytotoxicity of ARQ analogues; 4) the 1,1-dimethyl-2-propenyl group in the indole ring is not important for the cytotoxic activity of ARQ.

METABOLIC PRODUCTS OF ASPERGILLUS TERREUS. VI. METABOLITES OF THE STRAIN IFO 8835. (3). THE ISOLATION AND CHEMICAL STRUCTURES OF COLORLESS METABOLITES

Seven colorless metabolites related to asterriquinones and one colorless compound of another type were isolated from Aspergillus terreus IFO 8835, and their chemical structures were determined.Keywords-asterriquinones, Aspergillus terreus; IFO 8835; indolyl; indoline; nicotinyl