Asterriquinone

Base Information

• Chemical Name: Asterriquinone
• CAS No.: 60696-52-8
• Molecular Formula: C32H30N2O4
• Molecular Weight: 506.599
• NSC Number: 289487
• UNII: JV64RB1EJO
• DSSTox Substance ID: DTXSID90209505
• Nikkaji Number: J17.914K
• Wikidata: Q27122909
• Metabolomics Workbench ID: 57941
• ChEMBL ID: CHEMBL1966265
• Mol file: 60696-52-8.mol

Synonyms:asterriquinone;NSC 289487;NSC-289487

Chemical Property of Asterriquinone

Chemical Property:

• Vapor Pressure: 3.92E-22mmHg at 25°C
• Boiling Point: 726.2°C at 760 mmHg
• Flash Point: 393°C
• PSA: 84.46000
• Density: 1.2g/cm³
• LogP: 6.82840
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 506.22055744
• Heavy Atom Count: 38
• Complexity: 1010

Purity/Quality:

95%+ ^*data from raw suppliers

ASTERRIQUINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C=C)N1C=C(C2=CC=CC=C21)C3=C(C(=O)C(=C(C3=O)O)C4=CN(C5=CC=CC=C54)C(C)(C)C=C)O
• General Description: Asterriquinone is a biologically significant natural product characterized by its 3-indolyl-2,5-dihydroxybenzoquinone substructure, known for antitumor properties and other bioactivities. Its synthesis involves indole condensation with quinones, followed by oxidation and hydrolysis, or palladium-catalyzed N-annulation for sterically demanding N-substituted derivatives like demethylasterriquinone A1, highlighting its relevance in medicinal chemistry.

Technology Process of Asterriquinone

There total 7 articles about Asterriquinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2,5-dichloro-3,6-bis(1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione (1001099-63-3) → asterriquinone (60696-52-8)

Guidance literature:

With sodium hydroxide; In methanol; for 30h; Heating;

DOI:10.1039/b712227f

Reference yield: 72.0%

asterriquinone dimethyl ether (60924-75-6) → asterriquinone (60696-52-8)

Guidance literature:

With potassium hydroxide; In ethanol; for 1.5h; Heating;

Reference yield: 70.0%

2,5-bis[1-(1,1-dimethylallyl)-1H-indol-3-yl]-3,6-diethoxy-[1,4]benzoquinone (477883-73-1) → asterriquinone (60696-52-8)

Guidance literature:

With potassium hydroxide; In ethanol; at 70 ℃; for 1h;

DOI:10.1021/jo020182a

upstream raw materials:

asterriquinone dimethyl ether

2,5-bis<1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl>-3-acetoxy-6-hydroxy-2,5-cyclohexadiene-1,4-dione

2,5-bis[1-(1,1-dimethylallyl)-1H-indol-3-yl]-3,6-diethoxy-[1,4]benzoquinone

2,5-dibromo-3,6-diethoxy-1,4-benzoquinone

Downstream raw materials:

asterriquinone dimethyl ether

Refernces

Synthesis of 3-Indolyl-2,5-dihydroxybenzoquinones

10.1021/ol006852l

The research describes a novel and efficient method for synthesizing 3-indolyl-2,5-dihydroxybenzoquinones, a substructure found in biologically significant natural products like the asterriquinones, which are known for their antitumor properties and other biological activities. The purpose of the study is to develop a synthetic route that could be used in the total syntheses of asterriquinones or to prepare reagents for probing the biological activity of indolylquinones. The process involves the acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone, followed by DDQ oxidation, resulting in dichloroquinones that are then hydrolyzed to produce the 3-indolyldihydroxybenzoquinones.

Palladium-catalysed N-annulation routes to indoles: The synthesis of indoles with sterically demanding N-substituents, including demethylasterriquinone A1

10.1039/b712227f

The research aims to develop a method for synthesizing indoles with sterically demanding N-substituents using palladium-catalysed tandem aryl and alkenyl C–N bond formation. The study addresses the challenge of synthesizing N-substituted indoles, which are important for their biological and medicinal properties but difficult to produce due to the low nucleophilicity of indole nitrogen atoms. The researchers optimized a catalyst system using Pd(OAc)2, HBF4–PtBu3 ligand, and NaOtBu as base in toluene solvent at 130°C to achieve efficient coupling of bulky amines with dihalogenated styrenes. They demonstrated the versatility of their method by synthesizing a range of indoles with various sterically demanding N-nucleophiles and different styrene substrates. The utility of this method was further highlighted by a short synthesis of the natural product demethylasterriquinone A1, showcasing the potential for creating complex indole-based structures with significant biological functions.