253443-45-7

Basic information

• Product Name: 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione
• Synonyms: 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione
• CAS NO: 253443-45-7
• Molecular Weight: 299.301
• Mol File: 253443-45-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione(253443-45-7)
• EPA Substance Registry System: 2-[3-(4-fluorophenoxy)propyl]-1H-isoindole-1,3(2H)-dione(253443-45-7)

Safety Data

• Hazardous Substances Data: 253443-45-7(Hazardous Substances Data)

Upstream product

• 371-41-5 4-Fluorophenol 
• 883-44-3 N-(3-hydroxypropyl)phthalimide 
• 1716-42-3 1-(3-chloropropoxy)-4-fluorobenzene 
• 1074-82-4 potassium phtalimide 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 

Downstream Products

• 116753-54-9 3-(4-fluorophenoxy)propan-1-amine 

Relevant articles and documents

AMIDOPROPOXYPHENYL OREXIN RECEPTOR ANTAGONISTS

The present invention is directed to amidopropoxyphenyl compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved.

Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT(1C)-selective antagonist

DOM [i.e., 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane] is a 5- HT(1C/2) serotonin agonist that exerts stimulus control of behavior in animals. In order to determine if the discriminative stimulus effect of DOM is 5-HT(1C)- or 5-HT2-mediated, it would be informative to conduct tests of stimulus antagonism with a 5-HT(1C)- or 5-HT2-selective antagonist. To date, no such agents exist. Although the neuroleptic agent spiperone binds at D2 dopamine receptors and 5-HT(1A) serotonin receptors, (a) it displays about a 1000-fold selectivity for 5-HT2 versus 5-HT(1C) sites and (b) it has been used as a '5-HT2-selective' antagonist. Because spiperone is a behaviorally disruptive agent, it is not suitable for use in drug-discrimination studies. Using the spiperone molecule as a starting point, a limited structure- affinity investigation was conducted in order to identify a suitable antagonist with high affinity and selectivity for 5-HT2 receptors, and yet an antagonist that might lack the disruptive actions of spiperone. Various modifications of the spiperone molecule were examined, but most resulted in decreased 5-HT2 affinity or in loss of selectivity. One compound, 8-[3-(4- fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (26), was shown to bind at 5-HT2 sites with high affinity (K(i) = 2 nM) and >2,000- fold selectivity versus 5-HT(1C) sites. In tests of stimulus antagonism using rats trained to discriminate 1 mg/kg of DOM from saline vehicle, 26 behaved as a potent antagonist (ED50 = 0.003 mg/kg) and lacked the disruptive effects associated with spiperone. As such, (a) it would appear that the DOM stimulus is primarily a 5-HT2-mediated, and not 5-HT(1C)-mediated, phenomenon, and (b) compound 26 may find application in other pharmacologic investigations where spiperone may not be a suitable antagonist.