7617-76-7

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Phenoxy-propylamine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drug molecules. Its electron-donating nature and structural features make it a suitable candidate for creating active pharmaceutical ingredients.
Used in Organic Compound Synthesis:
In the realm of organic chemistry, 3-Phenoxy-propylamine serves as a building block for the synthesis of a wide range of organic compounds. Its unique structure allows for the formation of diverse chemical entities, expanding the scope of organic synthesis.
Used as a Reagent in Chemical Reactions:
3-Phenoxy-propylamine is utilized as a reagent in various chemical reactions due to its electron-donating properties. This characteristic makes it instrumental in facilitating specific types of chemical transformations, such as the formation of new bonds or the alteration of existing ones.
Used in Research and Development:
In the scientific community, 3-Phenoxy-propylamine is employed in research and development for exploring its potential applications and understanding its chemical behavior. This helps in advancing the knowledge of chemical compounds and their uses in different fields.
Used in Chemical Analysis:
3-Phenoxy-propylamine can also be used in chemical analysis to study the properties of other compounds or to develop new analytical methods. Its unique structure and reactivity make it a valuable tool for probing chemical systems and understanding reaction mechanisms.

InChI:InChI=1/C9H13NO/c10-7-4-8-11-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,10H2

Upstream product

• 588-63-6 3-phenoxypropyl bromide 
• 83708-38-7 (3-phthalimidopropyl)-phenyl ether 
• 104053-84-1 N-3-phenoxypropylpropionamide 
• 60-29-7 diethyl ether 
• 3055-86-5 3-phenoxypropionitrile 
• 7647-01-0 hydrogenchloride 
• 591-50-4 iodobenzene 
• 156-87-6 propan-1-ol-3-amine 
• 139-02-6 sodium phenoxide 
• 108-95-2 phenol 
• 6180-61-6 3-phenoxypropanol 
• 104053-83-0 N-3-phenoxypropylacetamide 

Downstream Products

• 101867-50-9 3,3'-(3-phenoxy-propylimino)-di-propionic acid dimethyl ester 
• 857582-24-2 N-[5-(3-phenoxy-propylamino)-pentyl]-benzamide 

Relevant academic research and scientific papers

Aqueous olefin hydroformylation using water-soluble mono- and trinuclear N,O-chelate rhodium(I)-aryl ether precatalysts

Water-soluble, sulfonated, salicylaldiminato-aryl ether mono- (7) and trimeric (8) ligands were prepared and reacted with the [Rh(μ-Cl)(η2:η2?COD)]2 dimer to yield the corresponding water-soluble mononuclear (9) and trinuc

Discovery of N-Aryloxypropylbenzylamines as Voltage-Gated Sodium Channel NaV1.2-Subtype-Selective Inhibitors

We previously reported that a lipophilic N-(4′-hydroxy-3′,5′-di-tert-butylbenzyl) derivative (1) of the voltage-gated sodium channel blocker mexiletine, was a more potent sodium channel blocker in vitro and in vivo. We demonstrate that replacing the chiral methylethylene linker between the amine and di-tert-butylphenol with an achiral 1,3-propylene linker (to give (2)) maintains potency in vitro. We synthesized 25 analogues bearing the 1,3-propylene linker and found that minor structural changes resulted in pronounced changes in state dependence of blocking human NaV1.2 and 1.6 channels by high-throughput patch-clamp analysis. Compared to mexiletine, compounds 1 and 2 are highly selective NaV1.2 inhibitors and >500 times less potent in inhibiting NaV1.6 channels. On the other hand, a derivative (compound 4) bearing 2,6-dimethoxy groups in place of the 2,6-dimethyl groups found in mexiletine was found to be the most potent inhibitor, but is nonselective against both channels in the tonic, frequency-dependent and inactivated states. In a kindled mouse model of refractory epilepsy, compound 2 inhibited seizures induced by 6 Hz 44 mA electrical stimulation with an IC50 value of 49.9±1.6 mg kg?1. As established sodium channel blockers do not suppress seizures in this mouse model, this indicates that 2 could be a promising candidate for treating pharmaco-resistant epilepsy.

Direct Primary Amination of Alkylmetals with NH-Oxaziridine

A method for the primary electrophilic amination of primary, secondary, and tertiary organometallic substrates from a bench-stable NH-oxaziridine reagent is described. This facile and highly chemoselective transformation occurs at ambient temperature and without transition metal catalysts or purification by column chromatography to provide alkylamine products in a single step. Density functional theory (DFT) calculations revealed that, despite the basicity of alkylmetals, the direct NH-transfer pathway is favored over proton and O-transfer.

Virtual screening for novel Atg5-Atg16 complex inhibitors for autophagy modulation

Two hit compounds (14 and 62) were identified using virtual high throughput screening (vHTS) inhibiting the autophagy process in A2780 ovarian cancer cells. The expression levels of the LC3-II and p62 autophagy marker proteins were monitored using Western blotting. Preliminary structure activity relationship (SAR) study of close structural analogues revealed another active compound 38. The three active compounds were tested in the MCF-7 human breast cancer cells and severe reduction of autophagosomes formation was observed confirming the activity of the inhibitors. The docking scaffold used for the vHTS was a lipophilic cleft on the Atg5 protein, which is occupied by a phenylalanine residue in the Atg16 polypeptide. To the best of our knowledge this is the first report on inhibitors that specifically modulate autophagy by directly inhibiting autophagy specific proteins, which is significant due the role autophagy plays in a number of morbid diseases such as cancer. This journal is

Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-β aggregation

A series of 9-N-substituted berberine derivatives were synthesized and biologically evaluated as antioxidant and inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase and amyloid-β aggregation. Most of these compounds exhibited very good antioxidant activities, inhibitive activities of AChE and amyloid-β aggregation. Among them, compound 8d, (o-methylphenethyl)amino linked at the 9-position of berberine, was found to be a good antioxidant (with 4.05 μM of Trolox equivalents), potent inhibitor of AChE (an IC50 value of 0.027 μM), and high active inhibitor of amyloid-β aggregation (an IC50 value of 2.73 μM).

Copper-catalyzed Ullmann coupling under ligand- and additive- free conditions. Part 1: O-Arylation of phenols with aryl halides

O-Arylation of a wide variety of substituted phenols and aliphatic alcohols with aryl halides catalyzed by copper iodide under mild ligand and additive free conditions (nBu4NBr, DMF, K3PO4, reflux, 22 h) is accomplished in good to excellent product yields (up to 95%).

Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists

A combination of benzoxazole, phenoxyalkyl side chain, and phenoxybutyric acids was identified as a highly potent and selective human peroxisome proliferator-activated receptor α (PPARα) agonist. The synthesis, structure-activity relationship (SAR) studies, and in vivo activities of the representative compounds are described.

New formation of 4,5,6,7-tetrahydroisoindoles

The high-yield syntheses of 4,5,6,7-tetrahydro-isoindoles from N-substituted isoindolines under palladium catalyzed hydrogenation conditions are reported. Mechanistic study with deuterated and saturated substrates show extensive H/D exchange and the essence of aromaticity in this transformation.

Polymer bound iminodicarbonate: A new ammonia equivalent for solid-phase synthesis of primary amines

A polymer bound iminodicarbonate has been designed and its use in solid-phase synthesis of primary amines is reported. (C) Elsevier Science Ltd.

COMPOUNDS AND METHODS OF TREATING PSYCHOSIS AND SCHIZOPHRENIA

This invention relates to compounds that are antagonists of dopamine D4 receptors, and to methods of treating psychosis and schizophrenia using a compound that is an antagonist of dopamine D4 receptors.