105277-69-8

Basic information

• Product Name: 7-(3-chloropropoxy)-4H-chroMen-4-one
• Synonyms: 7-(3-chloropropoxy)-4H-chroMen-4-one
• CAS NO: 105277-69-8
• Molecular Formula: C₁₂H₁₁ClO₃
• Molecular Weight: 238.66694
• Mol File: 105277-69-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-(3-chloropropoxy)-4H-chroMen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(3-chloropropoxy)-4H-chroMen-4-one(105277-69-8)
• EPA Substance Registry System: 7-(3-chloropropoxy)-4H-chroMen-4-one(105277-69-8)

Safety Data

• Hazardous Substances Data: 105277-69-8(Hazardous Substances Data)

Upstream product

• 59887-89-7 7-hydroxy-4H-chromen-4-one 
• 109-70-6 1.3-chlorobromopropane 
• 172739-45-6 1-<4-(3-chloropropoxy)-2-hydroxyphenyl>-1-ethanone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 172739-46-7 (E)-1-[4-(3-Chloro-propoxy)-2-hydroxy-phenyl]-3-dimethylamino-propenone 

Downstream Products

• 105277-58-5 7-[3-(4-(3-methylphenyl)piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 105277-62-1 7-[3-(4-(2-chlorophenyl)-1-piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 105277-55-2 7-[3-(4-(2-methoxyphenyl)piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 131323-73-4 7-[3-(4-Phenyl-[1,4]diazepan-1-yl)-propoxy]-chromen-4-one 
• 105277-65-4 7-[3-(4-(3-hydroxyphenyl)piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 131323-58-5 7-[3-(2,3,5,6-Tetrahydro-[1,2']bipyrazinyl-4-yl)-propoxy]-chromen-4-one 
• 213891-14-6 7-{3-[(3-Hydroxy-benzyl)-methyl-amino]-propoxy}-chromen-4-one 
• 105277-54-1 7-{3-[4-(3-Chloro-phenyl)-piperazin-1-yl]-propoxy}-chromen-4-one 
• 131323-68-7 4-[3-(4-Oxo-4H-chromen-7-yloxy)-propyl]-1-phenyl-piperazine-2,6-dione 
• 105277-53-0 7-{3-[4-(2,3-Dimethyl-phenyl)-piperazin-1-yl]-propoxy}-chromen-4-one 
• 105277-60-9 7-[3-(4-(4-fluorophenyl)piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 105277-66-5 7-[3-(4-(3,4-dimethylphenyl)piperazinyl)-propoxy]-4H-1-benzopyran-4-one 
• 105277-63-2 7-[3-(4-(3,4-dichlorophenyl)piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 131323-76-7 7-{3-[Ethyl-(3-phenyl-propyl)-amino]-propoxy}-chromen-4-one 

Relevant articles and documents

7-[3-(1-piperidinyl)propoxy]chromenones as potential atypical antipsychotics. 2. Pharmacological profile of 7-[3-[4-(6-fluoro-1,2- benzisoxazol-3-yl)piperidin-1-yl] propoxy]-3-(hydroxymethyl)chromen-4-one (abaperidone, FI-8602)

A series of novel 7-[3-(1-piperidinyl)propoxy]chromenones was synthesized and tested as potential antipsychotics in several in vitro and in vive assays. The compounds possessed good affinity for D2 receptors, together with a greater affinity for 5-HT2 receptors, a profile which has been proposed as a model for atypical antipsychotics. Several agents also displayed a high potency in the climbing mice assay on oral administration, suggesting a potent antipsychotic effect as compared to reference standards. Compound 23 was selected for further pharmacological evaluation. Induction of catalepsy and inhibition of stereotypies weaker than standards, along with a lower increase in serum prolactin levels, were indicative of a potential atypical profile for this compound. From these results, 7-[3-[4-(6-fluoro- 1,2-benzisoxazol-3-yl)piperidin1-yl]propoxy]-3-(hydroxymethyl)chromen-4-one (23, abaperidone) has been proposed for clinical evaluation in humans as a potential atypical antipsychotic.

Acetylcholinesterase inhibitors: Synthesis and structure-activity relationships of ω-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)- methyl]aminoalkoxyheteroaryl derivatives

Acetylcholinesterase (ACHE) inhibitors are one of the most actively investigated classes of compounds in the search for an effective treatment of Alzheimer's disease. This work describes the synthesis, AChE inhibitory activity, and structure-activity relationships of some compounds related to a recently discovered series of AChE inhibitors: the ω-[N-methyl-N-(3- alkylcarbamoyloxyphenyl)methyl]aminoalkoxyxanthen-9-ones. The influence of structural variations on the inhibitory potency was carefully investigated by modifying different parts of the parent molecule, and a theoretical model of the binding of one representative compound to the enzyme was developed. The biological properties of the series were investigated in some detail by considering not only the activity on isolated enzyme but the selectivity with respect to butyrylcholinesterase (BuChE) and the in vitro inhibitory activity on rat cerebral cortex as well. Some of the newly synthesized derivatives, when tested on isolated and/or AChE-enriched rat brain cortex fraction, displayed a selective inhibitory activity and were more active than physostigmine. In particular, compound 13, an azaxanthone derivative, displayed the best rat cortex AChE inhibition (190-fold higher than physostigmine), as well as a high degree of enzyme selectivity (over 60-fold more selective for AChE than for BuChE). When tested in the isolated enzyme, compound 13 was less active, suggesting some differences either in drug availability/biotransformation or in the inhibitor-sensitive residues of the enzyme when biologically positioned in rat brain membranes.

4-p-fluorobenzoyl-1-piperidinyl-propoxy-chromen-4-one derivatives, their preparation and their use in the treatment of psychosis and schizophrenia

The present invention relates to new chromene compounds of the general formula (I): STR1 wherein R1 and R2 are hydrogen, alkyl having from 1 to 4 carbon atoms, halogen, trifluoromethyl, optionally substituted phenyl, or hydroxymethyl

7-[3-(1-piperidinyl)propoxy]chromenones as potential atypical antipsychotics

Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)-4- oxobutyl]piperazine), a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1- piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.

Dopamine autoreceptor agonists as potential antipsychotics. 2. (Aminoalkoxy)-4H-1-benzopyran-4-ones

The synthesis and pharmacological properties of a novel type of [(arylpiperazinyl)alkoxy]-4H-1-benzopyran-4-ones with dopaminergic activity are described. The nature of the arylpiperazine (AP) moiety determines the dopamine (DA) agonist/antagonist character of this series of compounds; when the aryl portion of the AP is unsubstituted the compounds appear to be DA autoreceptor agonists while substituted aryl groups seem to impart DA antagonist activity. A heterocyclic piperazine, 7-[3-[4-(2-pyridinyl)-1-piperazinyl]propoxy]-4H-1-benzopyran-4-one (31, PD 119819) has been identified as an extremely selective DA autoreceptor agonist in tests that include [3H]haloperiodol binding, inhibition of spontaneous locomotor activity, inhibition of brain DA synthesis, inhibition of brain DA neuronal firing, stereotypy assessment, and reversal of 6-hydroxydopamine (6-OHDA) induced akinesia in rats. In addition, 31 possesses good oral activity in the Sidman avoidance test in squirrel monkeys, a predictor of clinical antipsychotic efficacy. In another primate model, 31 has been found to lack the liability for extrapyramidal side effects observed with currently available antipsychotic drugs.

4H-1-benzopyran-4-ones and their sulfur containing analogs

Novel 4H-1-benzopyran-4-ones and their sulfur containing analogs are disclosed which are efficacious for the treatment of psychosis including schizophrenia.