215923-54-9

Basic information

• Product Name: CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P
• Synonyms: CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P;(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(piperidin-1-yl)Methanone;(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-piperidinylmethanone;1-(2,3-Dihydro-1,4-benzodioxin-6-ylcarbonyl)piperidine;1-(1,4-Benzodioxan-6-ylcarbonyl)piperidine;CX-546;Methanone,(2,3-dihydro-1,4-benzodioxin-6-yl)-1-piperidinyl-;BDP 17
• CAS NO: 215923-54-9
• Molecular Formula: C14H17NO3
• Molecular Weight: 247.29
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;AMPA receptor potentiator which is specifically bound to agonist bound non-desensitized receptors.
• Mol File: 215923-54-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 422.8 °C at 760 mmHg
• Flash Point: 209.5 °C
• Appearance: white to off-white/
• Density: 1.215 g/cm³
• Vapor Pressure: 2.34E-07mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥10mg/mL
• PKA: -1.08±0.20(Predicted)
• CAS DataBase Reference: CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P(CAS DataBase Reference)
• NIST Chemistry Reference: CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P(215923-54-9)
• EPA Substance Registry System: CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P(215923-54-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 215923-54-9(Hazardous Substances Data)

Usage

Description

CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P), also known as a benzoylpiperidine derivative ampakine, is an analog of CX516. It is a compound that has been developed to enhance the function of the glutamatergic receptor α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) in mice.

Uses

Used in Pharmaceutical Industry:
CX546 (1-(1,4-BENZODIOXAN-6-YLCARBONYL)P) is used as a positive allosteric modulator for the glutamatergic receptor AMPA in mice. This application is significant because it has the potential to improve the function of the AMPA receptor, which plays a crucial role in cognitive processes and synaptic plasticity. By modulating the AMPA receptor, CX546 may contribute to the development of new therapeutic strategies for various neurological and psychiatric disorders.

Biological Activity

AMPA receptor potentiator. Binds specifically to the agonist bound non-desensitized receptor, most likely destabilizing the desensitized receptor conformation. Enhances cognitive function in rats.

Biochem/physiol Actions

CX546 has antipsychotic functionality and has the potential to treat schizophrenia. It improves the defects associated with the prepulse inhibition (PPI) and latent inhibition (LI)?in mice lacking metabotropic glutamate receptor type 5 (mGluR5). Additionally, CX546 potentiates synaptic plasticity, elicits neuroprotection and promotes the neurotrophin expression.

InChI:InChI=1/C14H17NO3/c16-14(15-6-2-1-3-7-15)11-4-5-12-13(10-11)18-9-8-17-12/h4-5,10H,1-3,6-9H2

Upstream product

• 110-89-4 piperidine 
• 201230-82-2 carbon monoxide 
• 52287-51-1 6-bromo-1,4-benzodioxane 
• 57744-67-9 6-iodo-1,4-benzodioxane 
• 67-66-3 chloroform 
• 4442-54-0 2,3-dihydro-1,4-benzodioxin-6-carboxylic acid 

Relevant articles and documents

Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis

A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.

Chloroform as a Carbon Monoxide Precursor: In or Ex Situ Generation of CO for Pd-Catalyzed Aminocarbonylations

Conditions for the rapid hydrolysis of chloroform to carbon monoxide (CO) using heterogeneous CsOH·H2O are described. CO and 13CO can be generated cleanly and rapidly under mild conditions and can be captured either in or ex situ in palladium-catalyzed aminocarbonylation reactions. Utilizing only 1-3 equiv of CO allows for the aminocarbonylation of aryl, vinyl, and benzyl halides with a wide variety of primary and secondary amines giving amide products in good to excellent yields. (Chemical Equation Presented).

SYSTEM PROVIDING CONTROLLED DELIVERY OF GASEOUS CO FOR CARBONYLATION REACTIONS

A carbonylation system comprising at least one carbon monoxide producing chamber and at least one carbon monoxide consuming chamber forming an interconnected multi-chamber system, said interconnection allowing carbon monoxide to pass from the at least one carbon monoxide producing chamber to the at least one carbon monoxide consuming chamber, said at least one carbon monoxide producing chamber containing a reaction mixture comprising a carbon monoxide precursor and a catalyst, said at least one carbon monoxide consuming chamber being suitable for carbonylation reactions, said interconnected multi- chamber system being sealable from the surrounding atmosphere during carbonylation.