N-Cyclohexyl-2-(N-(3-fluorophenyl)-2-(2-methyl-1H-imidazol-1-yl)acetamido)-2-(o-tolyl)acetamide

Base Information

• Chemical Name: N-Cyclohexyl-2-(N-(3-fluorophenyl)-2-(2-methyl-1H-imidazol-1-yl)acetamido)-2-(o-tolyl)acetamide
• CAS No.: 1355326-35-0
• Molecular Formula: C27H31FN4O2
• Molecular Weight: 462.567
• Mol file: 1355326-35-0.mol

Synonyms:CS-1429;AGI5198;AGI-5198||AGI5198|AGI 5198|IDH C35;QCR-214;

Chemical Property of N-Cyclohexyl-2-(N-(3-fluorophenyl)-2-(2-methyl-1H-imidazol-1-yl)acetamido)-2-(o-tolyl)acetamide

Chemical Property:

• Boiling Point: 707.6±60.0 °C(Predicted)
• PKA: 14.02±0.20(Predicted)
• PSA: 67.23000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 5.25330
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble3mg/mL, clear

Purity/Quality:

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

AGI5198 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Description: AGI-5198 (135526-35-0) is a potent (IC50?= 70 nM) inhibitor of mutant isocitrate dehydrogenase 1(IDH1).1? It is selective for the R132H-IDH1 mutant and does not affect wild type cells.2? This mutation results in loss-of-function for oxidative decarboxylation of isocitrate and gain-of-function for production of the oncometabolite R-2-hydroxyglutarate (R-2HG) from alpha-ketoglutarate (2-OG).
• Uses: AGI5198 inhibits mutant IDH1 (isocitrate dehydrogenase 1) in cancer cells which delays growth and promotes differentiation of the glioma cells. AGI-5198 has been used as a negative control in ligand dilution series.

Technology Process of N-Cyclohexyl-2-(N-(3-fluorophenyl)-2-(2-methyl-1H-imidazol-1-yl)acetamido)-2-(o-tolyl)acetamide

There total 4 articles about N-Cyclohexyl-2-(N-(3-fluorophenyl)-2-(2-methyl-1H-imidazol-1-yl)acetamido)-2-(o-tolyl)acetamide 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: 42.0%

2-methylimidazole (693-98-1) + 2-chloro-N-(2-(cyclohexylamino)-2-oxo-1-(o-tolyl)ethyl)-N-(3-fluorophenyl)acetamide (1355324-97-8) → AGI-5198 (1355326-35-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Reflux;

DOI:10.1021/ml300225h

Reference yield:

meta-fluoroaniline (372-19-0) → AGI-5198 (1355326-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 0.67 h / 20 °C

1.2: 0.33 h / 20 °C

1.3: 3 h / 20 °C

2.1: triethylamine / dichloromethane / 20 °C / Reflux

With triethylamine; In methanol; dichloromethane; 1.1: |Ugi Condensation / 1.2: |Ugi Condensation / 1.3: |Ugi Condensation;

DOI:10.1021/ml300225h

Reference yield:

2-methylphenyl aldehyde (529-20-4) → AGI-5198 (1355326-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methanol / 0.67 h / 20 °C

1.2: 0.33 h / 20 °C

1.3: 3 h / 20 °C

2.1: triethylamine / dichloromethane / 20 °C / Reflux

With triethylamine; In methanol; dichloromethane; 1.1: |Ugi Condensation / 1.2: |Ugi Condensation / 1.3: |Ugi Condensation;

DOI:10.1021/ml300225h

upstream raw materials:

2-methylimidazole

2-chloro-N-(2-(cyclohexylamino)-2-oxo-1-(o-tolyl)ethyl)-N-(3-fluorophenyl)acetamide

meta-fluoroaniline

2-methylphenyl aldehyde

Downstream raw materials:

N-cyclohexyl-2-(N-(3-fluorophenyl)-2-(2-methyl-1H-imidazol-1-yl)acetamido)-2-(o-tolyl)acetamide hydrochloric acid

Refernces

• 1、 -. "THERAPEUTICALLY ACTIVE COMPOSITIONS AND THEIR METHOD OF USE". Page/Page column 151. . Retrieved 2012/02/02.