1334127-17-1

Basic information

• Product Name: 1-(6-cyanobenzo[d]thiazol-2-yl)-3-(4-methoxybenzyl)urea
• Synonyms: 1-(6-cyanobenzo[d]thiazol-2-yl)-3-(4-methoxybenzyl)urea
• CAS NO: 1334127-17-1
• Molecular Weight: 338.39
• Mol File: 1334127-17-1.mol

Chemical Properties

• CAS DataBase Reference: 1-(6-cyanobenzo[d]thiazol-2-yl)-3-(4-methoxybenzyl)urea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-cyanobenzo[d]thiazol-2-yl)-3-(4-methoxybenzyl)urea(1334127-17-1)
• EPA Substance Registry System: 1-(6-cyanobenzo[d]thiazol-2-yl)-3-(4-methoxybenzyl)urea(1334127-17-1)

Safety Data

• Hazardous Substances Data: 1334127-17-1(Hazardous Substances Data)

Upstream product

• 19759-66-1 2-amino-6-cyanobenzthiazole 
• 56651-60-6 4-methoxybenzyl isocyanate 
• 2393-23-9 4-methoxy-benzylamine 
• 873-74-5 4-Aminobenzonitrile 
• 68867-21-0 4-amino-3-thiocyanatobenzonitrile 

Downstream Products

• 1334128-04-9 C₁₇H₁₅N₇O₂S 

Relevant articles and documents

1-Aryl-3-(4-methoxybenzyl)ureas as potentially irreversible glycogen synthase kinase 3 inhibitors: Synthesis and biological evaluation

Glycogen synthase kinase 3 (GSK-3)has become known for its multifactorial involvement in the pathogenesis of Alzheimer's disease. In this study, a benzothiazole- and benzimidazole set of 1-aryl-3-(4-methoxybenzyl)ureas were synthesised as proposed Cys199-targeted covalent inhibitors of GSK-3β, through the incorporation of an electrophilic warhead onto their ring scaffolds. The nitrile-substituted benzimidazolylurea 2b (IC50 = 0.086 ± 0.023 μM)and halomethylketone-substituted benzimidazolylurea 9b (IC50 = 0.13 ± 0.060 μM)displayed high GSK-3β inhibitory activity, in comparison to reference inhibitor AR-A014418 (1, IC50 = 0.072 ± 0.043)in our assay. The results suggest further investigation of 2b and 9b as potential covalent inhibitors of GSK-3β, since a targeted interaction might provide improved kinase-selectivity.

Synthesis and biological evaluation of glycogen synthase kinase 3 (GSK-3) inhibitors: An fast and atom efficient access to 1-aryl-3-benzylureas

The glycogen synthase kinase 3 (GSK-3) is implicated in multiple cellular processes and has been linked to the pathogenesis of Alzheimer's disease (AD). In the course of our research topic we synthesized a library of potent GSK-3 inhibitors. We utilized the urea scaffold present in the potent and highly selective GSK-3 inhibitor AR-A014418 (AstraZeneca). This moiety suits both (a) a convergent approach utilizing readily accessible building blocks and (b) a divergent approach based on a microwave heating assisted Suzuki coupling. We established a chromatography-free purification method to generate products with sufficient purity for the biological assays. The structure-activity relationship of the library provided the rationale for the synthesis of the benzothiazolylurea 66 (IC50 = 140 nM) and the pyridylurea 62 (IC 50 = 98 nM), which displayed two to threefold enhanced activity versus the reference compound 18 (AR-A014418: IC50 = 330 nM) in our assays.