IM-12

Base Information

• Chemical Name: IM-12
• CAS No.: 1129669-05-1
• Molecular Formula: C22H20FN3O2
• Molecular Weight: 377.4115032
• Mol file: 1129669-05-1.mol

Synonyms:IM-12;3-(4-fluorophenethylaMino)-1-Methyl-4-(2-Methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione;3-[[2-(4-fluorophenyl)ethyl]amino]-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione;3-(4-Fluorophenylethylamino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione IM-12;3-(4-Fluorophenylethylamino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione

Chemical Property of IM-12

Chemical Property:

• Melting Point: 187 °C
• Boiling Point: 600.2±55.0 °C(Predicted)
• PKA: 16.77±0.30(Predicted)
• PSA: 65.20000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 3.48620
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥9mg/mL

Purity/Quality:

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

3-((4-Fluorophenethyl)amino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Description: Glycogen synthase kinase 3β (GSK3β) is a constitutively active serine/threonine protein kinase implicated in several important regulatory processes. It can phosphorylate β-catenin, an intracellular signal transducer in the Wnt signaling pathway, which leads to β-catenin degradation. IM-12 is a non-symmetrically substituted indolylmaleimide that increases β-catenin levels by inhibiting GSK3β (IC50 = 53 nM). It has been shown to reduce proliferation and increase differentiation of a ReNCell VM cell line derived from human ventral midbrain. IM-12 is also reported to have a depolymerizing effect on in vitro tubulin assembly.
• Uses: 3-((4-Fluorophenethyl)amino)-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione acts as an enhancer of Wnt signalling, involved in cell proliferation or differentiation, via inhibition of glycogen synthase kinase 3 beta (GSK-3β).

Technology Process of IM-12

There total 2 articles about IM-12 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: 95.0%

1-methyl-3-bromo-4-(2-methyl-1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione (885701-91-7) + 4-fluoro-2-phenethylamine (1583-88-6) → 3-[[2-(4-fluorophenyl)ethyl]amino]-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (1129669-05-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 20 ℃; Reflux; Inert atmosphere;

DOI:10.1016/j.bmc.2010.07.045

Reference yield: 60.0%

1-methyl-3-bromo-4-(2-methyl-1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione (885701-91-7) + carbon monoxide (201230-82-2) + 4-fluoro-2-phenethylamine (1583-88-6) → 3-[[2-(4-fluorophenyl)ethyl]amino]-1-methyl-4-(2-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione (1129669-05-1) + C23H20FN3O3 (1129668-95-6)

Guidance literature:

With palladium diacetate; triethylamine; catacxium A; In 1,4-dioxane; at 100 ℃; for 16h; under 11251.1 Torr; Autoclave;

DOI:10.1002/ejoc.200800964

upstream raw materials:

1-methyl-3-bromo-4-(2-methyl-1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione

carbon monoxide

4-fluoro-2-phenethylamine

Refernces

• 1、 Brennfuehrer, Anne,Neumann, Helfried,Pews-Davtyan, Anahit,Beller, Matthias. "Catalytic and stoichiometric synthesis of novel 3-aminocarbonyl-, 3-alkoxycarbonyl-, and 3-amino-4-indolylmaleimides". supporting information; experimental part. p. 38 - 42. Retrieved 2009/05/31.