151057-13-5

Basic information

• Product Name: L-701,252
• Synonyms: L-701,252;7-CHLORO-3-(CYCLOPROPYL-CARBONYL)-4-HYDROXY-2(1H)-QUINOLINE;7-CHLORO-3-(CYCLOPROPYLCARBONYL)-4-HYDROXY-2(1H)-QUINOLINONE;7-CHLORO-3-(CYCLOPROPYLCARBONYL)-4-HYDROXY-2(1H)-QUINOLINE[L-701, 252];7-Chloro-3-(cyclopropanecarbonyl)-4-hydroxyquinolin-2(1H)-one
• CAS NO: 151057-13-5
• Molecular Formula: C13H10ClNO3
• Molecular Weight: 263.68
• Product Categories: Glutamate receptor
• Mol File: 151057-13-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 437.3 °C at 760 mmHg
• Flash Point: 218.3 °C
• Appearance: White crystalline solid
• Density: 1.573 g/cm³
• Vapor Pressure: 2.03E-08mmHg at 25°C
• Refractive Index: 1.694
• Storage Temp.: Desiccate at +4°C
• CAS DataBase Reference: L-701,252(CAS DataBase Reference)
• NIST Chemistry Reference: L-701,252(151057-13-5)
• EPA Substance Registry System: L-701,252(151057-13-5)

Safety Data

• Hazardous Substances Data: 151057-13-5(Hazardous Substances Data)

Usage

Biological Activity

An antagonist at the glycine-NMDA site (IC 50 = 420 nM). Also a potent systemic anticonvulsant.

InChI:InChI=1/C13H10ClNO3/c14-7-3-4-8-9(5-7)15-13(18)10(12(8)17)11(16)6-1-2-6/h3-6H,1-2H2,(H2,15,17,18)

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Relevant articles and documents

3-Acyl-4-hydroxyquinolin-2(1H)-ones. Systemically Active Anticonvulsants Acting by Antagonism at the Glycine Site of the N-Methyl-D-Aspartate Receptor Complex

Most full antagonists at the glycine site of the NMDA receptor contain a carboxylic acid, which we believe to be detrimental to penetration of the blood-brain barrier.By consideration of a pharmacophore, novel antagonists at this site have been designed in which the anionic functionality is a vinylogous acid, in the form of a 4-hydroxyquinolin-2(1H)-one.In this series, a 3-substituent is necessary for binding, and correct manipulation of this group leads to compounds such as the 3-(3-hydroxyphenyl)propargyl ester 24 (L-701,273), with an IC50 for displacement of -L-689,560 binding of 0.17 μM and Kb against NMDA in the cortical slice of 1.39 μM.Compounds were tested for their ability to prevent audiogenic seizure in DBA/2 mice; the most potent compound in this series is the cyclopropyl ketone 42 (L-701,252), with an ED50 of 4.1 mg/kg ip.A model is proposed for binding to the glycine site, in which an important interaction is of a putative receptor cation with the ?-system of the 3-substituent.