126245-46-3

Basic information

• Product Name: 1-BENZYL-3-CYANOACETYLUREA
• Synonyms: 1-BENZYL-3-CYANOACETYLUREA;2-Cyano-N-[[(phenylMethyl)aMino]carbonyl]acetaMide
• CAS NO: 126245-46-3
• Molecular Formula: C₁₁H₁₁N₃O₂
• Molecular Weight: 217.22
• Product Categories: Aromatics Compounds;Aromatics;Intermediates
• Mol File: 126245-46-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 171-174°C
• Appearance: /
• Density: 1.227g/cm³
• Refractive Index: 1.555
• Storage Temp.: -20°C Freezer
• Solubility: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-BENZYL-3-CYANOACETYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-3-CYANOACETYLUREA(126245-46-3)
• EPA Substance Registry System: 1-BENZYL-3-CYANOACETYLUREA(126245-46-3)

Safety Data

• Hazardous Substances Data: 126245-46-3(Hazardous Substances Data)

Usage

Description

1-BENZYL-3-CYANOACETYLUREA is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals, particularly anticonvulsant medications. It is a white crystalline solid with unique chemical properties that make it a valuable component in the development of drugs targeting seizure disorders.

Uses

Used in Pharmaceutical Industry:
1-BENZYL-3-CYANOACETYLUREA is used as an intermediate in the synthesis of anticonvulsant drugs for the treatment of epilepsy and other seizure disorders. Its chemical structure allows for the development of medications that can effectively manage and reduce the frequency of seizures, improving the quality of life for patients suffering from these conditions.
Used in Chemical Research:
As a white crystalline solid with distinct chemical properties, 1-BENZYL-3-CYANOACETYLUREA can also be utilized in chemical research and development. It may serve as a starting material or a building block for the creation of new compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C11H11N3O2/c12-7-6-10(15)14-11(16)13-8-9-4-2-1-3-5-9/h1-5H,6,8H2,(H2,13,14,15,16)

Upstream product

• 538-32-9 benzylurea 
• 372-09-8 cyanoacetic acid 
• 100-46-9 benzylamine 

Downstream Products

• 146494-87-3 3-Amino-2-oxo-1,4-diaza-spiro[4.5]decane-1,3-dicarboxylic acid 3-amide 1-benzylamide 
• 41862-11-7 1-benzyl-6-aminouracil 
• 138574-76-2 2-Oxo-1,4-diaza-spiro[4.5]dec-3-ene-1,3-dicarboxylic acid 3-amide 1-benzylamide 

Relevant articles and documents

Carboxylic acid-catalyzed one-pot synthesis of cyanoacetylureas and their cyclization to 6-aminouracils in guanidine ionic liquid

A novel, one-pot, carboxylic acid-catalyzed synthesis of cyanoacetylureas via in situ generated ureas and their cyclization to 6-aminouracils in the presence of the guanidine-based ionic liquid 1,1,3,3-tetramethylguanidine lactate [TMG][Lac] is described. The ureas were synthesized from amines and potassium cyanate, which on reaction with cyanoacetic acid in the presence of acetic anhydride in the same pot afforded cyanoacetylureas, which undergo cyclization in [TMG][Lac] as solvent as well as catalyst to afford 6-aminouracils. One-pot synthesis of cyanoacetylureas, efficient and rapid cyclization, better yield, shorter reaction time, easy workup procedure, and recyclability of the ionic liquid are some advantages of this procedure.

Structure-based optimization of potent and selective inhibitors of the tyrosine kinase erythropoietin producing human hepatocellular carcinoma receptor B4 (EphB4)

The tyrosine kinase EphB4 is an attractive target for drug design because of its recognized role in cancer-related angiogenesis. Recently, a series of commercially available xanthine derivatives were identified as micromolar inhibitors of EphB4 by high-throughput fragment-based docking into the ATP-binding site of the kinase domain. Here, we have exploited the binding mode obtained by automatic docking for the optimization of these EphB4 inhibitors by chemical synthesis. Addition of only two heavy atoms, methyl and hydroxyl groups, to compound 4 has yielded the single-digit nanomolar inhibitor 66, with a remarkable improvement of the ligand efficiency from 0.26 to 0.37 kcal/(mol per non-hydrogen atom). Compound 66 shows very high affinity for a few other tyrosine kinases with threonine as gatekeeper residue (Abl, Lck, and Src). On the other hand, it is selective against kinases with a larger gatekeeper. A 45 ns molecular dynamics (MD) simulation of the complex of EphB4 and compound 66 provides further validation of the binding mode obtained by fragment-based docking. 2009 American Chemical Society.

Synthesis of cyanacetylureas with a view to testing in Hymenolepis nana

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