Demethylasterriquinone B1

Base Information

• Chemical Name: Demethylasterriquinone B1
• CAS No.: 78860-34-1
• Molecular Formula: C₃₂H₃₀N₂O₄
• Molecular Weight: 506.601
• UNII: F6582H6JQW
• Nikkaji Number: J1.107.850H
• Wikidata: Q75057378
• Pharos Ligand ID: GV2NFX3VTCVR
• Metabolomics Workbench ID: 118716
• ChEMBL ID: CHEMBL18879
• Mol file: 78860-34-1.mol

Synonyms:demethyl-asterriquinone B1;demethylasterriquinone B-1;demethylasterriquinone B1;DMAQB-1;L 783281;L-783,281;L783281

Chemical Property of Demethylasterriquinone B1

Chemical Property:

• Vapor Pressure: 1.26E-25mmHg at 25°C
• Boiling Point: 780.2°C at 760 mmHg
• Flash Point: 425.6°C
• PSA: 106.18000
• Density: 1.335g/cm³
• LogP: 7.01170
• Storage Temp.: Desiccate at -20°C
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 506.22055744
• Heavy Atom Count: 38
• Complexity: 1090

Purity/Quality:

98%,99%, ^*data from raw suppliers

Demethylasterriquinone B1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=CC=C1)C(=CN2)C3=C(C(=O)C(=C(C3=O)O)C4=C(NC5=CC=CC=C54)C(C)(C)C=C)O)C
• Description: Demethylasterriquinone B1 (DMAQ B1) is a natural insulin mimic that activates insulin receptor tyrosine kinase (IRTK; EC50 = 6 μM). It less potently activates IGF1R and EGFR (EC50s = 100 μM for both). DMAQ B1 induces glucose uptake in adipocytes and skeletal muscle cells without activating proliferation. DMAQ B1 binds GAPDH in vitro.

Technology Process of Demethylasterriquinone B1

There total 34 articles about Demethylasterriquinone B1 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: 98.0%

4-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-3-hydroxy-6-[7-(3-methyl-but-2-enyl)-1H-indol-3-ylmethylene]-pyran-2,5-dione (245112-21-4) → 2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione (78860-34-1)

Guidance literature:

With sodium methylate; In methanol; at 23 ℃; for 3h;

DOI:10.1016/S0040-4039(99)00965-X

Reference yield: 78.0%

asterriquinone B1 (78708-35-7) → 2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione (78860-34-1)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 2h; Heating;

DOI:10.7164/antibiotics.54.105

Reference yield: 73.0%

3-[2,5-dichloro-4-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-3,6-dioxocyclohexa-1,4-dienyl]-7-(3-methylbut-2-enyl)indole-1-carboxylic acid tert-butyl ester (477883-78-6) → 2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione (78860-34-1)

Guidance literature:

With sodium hydroxide; In methanol; for 0.5h; Heating;

DOI:10.1021/jo020182a

upstream raw materials:

asterriquinone B1

2-[2-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-hydroxy-3-methyl-butyl)-1H-indol-3-yl]-[1,4]benzoquinone

4-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-3-hydroxy-6-[7-(3-methyl-but-2-enyl)-1H-indol-3-ylmethylene]-pyran-2,5-dione

2,5-dibromo-3-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-6-[7-(3-methylbut-2-enyl)-1H-indol-3-yl][1,4]benzoquinone

Downstream raw materials:

asterriquinone B1

Refernces

• 1、 Pirrung, Michael C,Li, Zhitao,Park, Kaapjoo,Zhu, Jin. "Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1.". . p. 7919 - 7926. Retrieved 2007/10/03.
• 2、 Liu, Kun,Wood, Harold B.,Jones, A. Brian. "Total synthesis of asterriquinone B1". . p. 5119 - 5122. Retrieved 2007/10/03.