Bisindolylmaleimide i

Base Information

• Chemical Name: Bisindolylmaleimide i
• CAS No.: 133052-90-1
• Molecular Formula: C₂₅H₂₄N₄O₂
• Molecular Weight: 412.491
• Hs Code.: 2925199590
• European Community (EC) Number: 603-702-0
• UNII: L79H6N0V6C
• DSSTox Substance ID: DTXSID50157932
• Nikkaji Number: J491.386H
• Wikipedia: BIM-1
• Wikidata: Q866357
• Pharos Ligand ID: CPGXB4PLDPJP
• Metabolomics Workbench ID: 67429
• ChEMBL ID: CHEMBL7463
• Mol file: 133052-90-1.mol

Synonyms:2-(1-(3-dimethylaminopropyl)indol-3-yl)-3-(indol-3-yl)maleimide;3-(1-(3-(dimethylamino)propyl)-1H-indol-3-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione;BIS-1 cpd;bisindolylmaleimide I;bisindoylmaleimide I;GF 109203X;GF-109203X;GF109203X;GFX 203290;Go 6850;Go-6850

Chemical Property of Bisindolylmaleimide i

Chemical Property:

• Appearance/Colour: orange solid
• Vapor Pressure: 1.19E-18mmHg at 25°C
• Melting Point: 208-210 °C
• Boiling Point: 685.6 °C at 760 mmHg
• PKA: 8.13±0.60(Predicted)
• Flash Point: 368.5 °C
• PSA: 70.13000
• Density: 1.3 g/cm³
• LogP: 3.97030
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~1 mg/mlsoluble
• Water Solubility.: Insoluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 412.18992602
• Heavy Atom Count: 31
• Complexity: 748

Purity/Quality:

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

GF 109203X ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCCN1C=C(C2=CC=CC=C21)C3=C(C(=O)NC3=O)C4=CNC5=CC=CC=C54
• Description: GF-109203X (133052-90-1) is a potent and selective protein kinase C inhibitor (IC50 = 10 nM; cAMP-dependent protein kinase IC50 = 2 μM and phosphorylase kinase IC50 = 0.7 μM). Inactive against the tyrosine kinases EGFR, PGDFR and Insulin receptor. Potent inhibitor of GSK-3β in cell lysates (IC50 = 360nM) and GSK-3β immunoprecipitates (IC50 = 170nM) derived from rat epididymal adipocytes.2 Cell permeable.
• Uses: Bisindolylmaleimide is used as a highly selective inhibitor of all PKC isoforms and slight inhibitor of GSK-3, used to selectively probe for PKC-mediated pathways for transduction of hormone, cytokine, and growth factor signals, very potent and selective inhibitor of protein kinase C.

Technology Process of Bisindolylmaleimide i

There total 14 articles about Bisindolylmaleimide i 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: 96.0%

dimethyl amine (124-40-3) + 3-[1-(3-methanesulfonyloxypropyl)-3-indolyl]-4-(3-indolyl)-1H-pyrrole-2,5-dione (203719-62-4) → bisindolylmaleimide I (133052-90-1)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 16h;

DOI:10.1021/jo980513c

Reference yield: 84.0%

2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0) + 1-(3-dimethylaminopropyl)indole-3-acetamide (203719-69-1) → bisindolylmaleimide I (133052-90-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo980513c

Reference yield:

2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleic acid anhydride (776262-13-6) + 2-(1-tert.-butoxycarbonyl-1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl)-N-methylmaleinimide (133053-48-2) + 2-(1H-indol-3-yl)-3-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-maleic acid anhydride hydrochloride + 3-(1H-indol-3-yl)-4-[1-{tert-butyloxycarbonyl}indol-3-yl]-1-methyl-1H-pyrrole-2,5-dione (119139-20-7) + 3-(Dimethylamino)propyl chloride (109-54-6) → bisindolylmaleimide I (133052-90-1)

Guidance literature:

With ammonium acetate; potassium hydroxide; sodium hydrogencarbonate; potassium carbonate; In methanol; ethanol; water; acetone; toluene;

upstream raw materials:

2-(3-indolyl)oxoacetic acid methyl ester

1-(3-dimethylaminopropyl)indole-3-acetamide

dimethyl amine

3-[1-(3-methanesulfonyloxypropyl)-3-indolyl]-4-(3-indolyl)-1H-pyrrole-2,5-dione

Refernces

• 1、 -. "Synthesis of bisindolylmaleimides". . . Retrieved 2008/06/13.
• 2、 Faul, Margaret M.,Winneroski, Leonard L.,Krumrich, Christine A.. "A New, Efficient Method for the Synthesis of Bisindolylmaleimides". . p. 6053 - 6058. Retrieved 2007/10/03.