AR-A014418

Base Information

• Chemical Name: AR-A014418
• CAS No.: 487021-52-3
• Molecular Formula: C₁₂H₁₂N₄O₄S
• Molecular Weight: 308.318
• Mol file: 487021-52-3.mol

Synonyms:Urea, N-[(4-methoxyphenyl)methyl]-N'-(5-nitro-2-thiazolyl)-;

Chemical Property of AR-A014418

Chemical Property:

• Melting Point: 208-210 C (dec.)
• Refractive Index: 1.666
• PSA: 137.31000
• Density: 1.464 g/cm³
• LogP: 3.36870
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: DMSO: ≥20mg/mL, clear, light yellow

Purity/Quality:

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

AR-AO 14418 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: AR-A 014418 (487021-52-3) is a selective glycogen synthase kinase 3 (GSK-3) inhibitor, IC50 = 104 nM. Inhibits β-amyloid-mediated neurodegeneration in hippocampal slices. Anti-inflammatory activity. Cell permeable. Active in rodent models.
• Uses: AR-A014418 has been used as an inhibitor of glycogen synthase kinase 3 (GSK3). Glycogen Synthase Kinase 3β (GSK-3β) inhibitor.

Technology Process of AR-A014418

There total 4 articles about AR-A014418 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: 97.0%

2-amino-5-nitro-1,3-thiazole (121-66-4,176384-36-4,8023-00-5) + N-(1H-imidazol-1-ylcarbonyl)-4-methoxybenzylamine → N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl)urea (487021-52-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/jo302084a

Reference yield: 25.0%

2-amino-5-nitro-1,3-thiazole (121-66-4,176384-36-4,8023-00-5) + bis(trichloromethyl) carbonate (32315-10-9) + 4-methoxy-benzylamine (2393-23-9) → N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl)urea (487021-52-3)

Guidance literature:

bis(trichloromethyl) carbonate; 4-methoxy-benzylamine; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1.25h; Inert atmosphere;

2-amino-5-nitro-1,3-thiazole; With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h; Inert atmosphere;

Reference yield:

4-methoxy-benzylamine (2393-23-9) → N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl)urea (487021-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / dichloromethane; water / 2.5 h / 0 °C

2: n-butyllithium / tetrahydrofuran; hexane / 20 °C

With n-butyllithium; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1016/j.bmcl.2011.06.131

upstream raw materials:

2-amino-5-nitro-1,3-thiazole

4-methoxybenzyl isocyanate

4-methoxy-benzylamine

bis(trichloromethyl) carbonate

Refernces

• 1、 -. "COMPOUNDS AND METHODS FOR TREATMENT OF CANCER BY INHIBITING ATG4B AND BLOCKING AUTOPHAGY". Page/Page column 30; 31; 33. . Retrieved 2017/03/14.
• 2、 Monte, Fabio Lo,Kramer, Thomas,Bol?nder, Alexander,Plotkin, Batya,Eldar-Finkelman, Hagit,Fuertes, Ana,Dominguez, Juan,Schmidt, Boris. "Synthesis and biological evaluation of glycogen synthase kinase 3 (GSK-3) inhibitors: An fast and atom efficient access to 1-aryl-3-benzylureas". supporting information; experimental part. p. 5610 - 5615. Retrieved 2011/10/09.