501925-31-1

Basic information

• Product Name: N-(5-CHLORO-2,4-DIMETHOXYPHENYL)-N'-(5-METHYL-3-ISOXAZOLYL)-UREA
• Synonyms: PNU 120596;N-(5-CHLORO-2,4-DIMETHOXYPHENYL)-N'-(5-METHYL-3-ISOXAZOLYL)-UREA;N-(5-Chloro-2,4-dimethoxphenyl)-N'-(5-methyl-3-isoxazolyl)-urea;1-(5-Chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea;Nsc 216666;Urea, N-(5-chloro-2,4-dimethoxyphenyl)-N'-(5-methyl-3-isoxazolyl)-
• CAS NO: 501925-31-1
• Molecular Formula: C13H14ClN3O4
• Molecular Weight: 311.72096
• Product Categories: Inhibitors
• Mol File: 501925-31-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 385 °C at 760 mmHg
• Flash Point: 186.6 °C
• Appearance: white to off-white/
• Density: 1.403
• Vapor Pressure: 3.94E-06mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Desiccate at +4°C
• Solubility: DMSO: >10mg/mL
• CAS DataBase Reference: N-(5-CHLORO-2,4-DIMETHOXYPHENYL)-N'-(5-METHYL-3-ISOXAZOLYL)-UREA(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-CHLORO-2,4-DIMETHOXYPHENYL)-N'-(5-METHYL-3-ISOXAZOLYL)-UREA(501925-31-1)
• EPA Substance Registry System: N-(5-CHLORO-2,4-DIMETHOXYPHENYL)-N'-(5-METHYL-3-ISOXAZOLYL)-UREA(501925-31-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 501925-31-1(Hazardous Substances Data)

Usage

Uses

PNU 120596 is a type II positive allosteric modulator.

Biological Activity

Positive allosteric modulator of α 7 neuronal nicotinic acetylcholine receptors (EC 50 = 216 nM), with no detectable effect on α 4 β 2, α 3 β 4 and α 9 α 10 receptors. Active in vivo following systemic administration.

Biochem/physiol Actions

An allosteric modulator of α7 nicotinic receptors, N-(5-chloro-2,4-dimethoxyphenyl)-N′-(5-methyl-3-isoxazolyl)-urea (PNU-120596), causes conformational changes in the extracellular ligand binding domain similar to those caused by acetylcholinePNU-120596 is a positive allosteric modulator selective for the α7 nicotinic acetylcholine receptor. PNU-120596 produces no detectable change in currents mediated by α4β2, α3β4, α9α10 nAChRs. It increases channel mean open time, but does not affect ion selectivity. It does not bind at the agonist binding site, but induces conformational changes similar to the natural effector.

references

[1] hurst r s, hajós m, raggenbass m, et al. a novel positive allosteric modulator of the α7 neuronal nicotinic acetylcholine receptor: in vitro and in vivo characterization. the journal of neuroscience, 2005, 25(17): 4396-4405.[2] bertrand d, gopalakrishnan m. allosteric modulation of nicotinic acetylcholine receptors. biochemical pharmacology, 2007, 74(8): 1155-1163.

InChI:InChI=1/C13H14ClN3O4/c1-7-4-12(17-21-7)16-13(18)15-9-5-8(14)10(19-2)6-11(9)20-3/h4-6H,1-3H3,(H2,15,16,17,18)

Upstream product

• 3405-77-4 5-methylisoxazole 3-carboxylic acid 
• 97-50-7 5-chloro-2,4-dimethoxyaniline 
• 61672-67-1 5-methyl-isoxazole-3-carbonyl azide 

Relevant articles and documents

Scalable, One-Pot, Microwave-Accelerated Tandem Synthesis of Unsymmetrical Urea Derivatives

We report a facile, microwave-accelerated, one-pot tandem synthesis of unsymmetrical ureas via a Curtius rearrangement. In this method, one-pot microwave irradiation of commercially available (hetero)aromatic acids and amines in the presence of diphenylphosphoryl azide enabled extremely rapid (1-5 min) construction of an array of unsymmetrical ureas in good to excellent yields. We demonstrate the utility of our method in the efficient, gram-scale synthesis of key biologically active compounds targeting the cannabinoid 1 and α7 nicotinic acetylcholine receptors.