5453-99-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyl-morpholin-2-one is used as a neurokinin-1 receptor antagonist for its potential role in treating various disorders related to the central nervous system. Its ability to block the neurokinin-1 receptor may contribute to its anti-anxiety and anti-depressant effects, making it a promising candidate for the development of new therapeutic agents.
Used in Mental Health Applications:
4-Benzyl-morpholin-2-one is used as an anti-anxiety agent for its potential to alleviate anxiety symptoms by modulating the neurokinin-1 receptor. This may provide a new approach to treating anxiety disorders and improving the quality of life for affected individuals.
Used in Antidepressant Therapy:
4-Benzyl-morpholin-2-one is used as an anti-depressant agent for its potential to improve mood and alleviate depressive symptoms. Its action as a neurokinin-1 receptor antagonist may contribute to its antidepressant effects, offering a novel therapeutic option for the treatment of depression.
Used in Substance Abuse and Addiction Treatment:
4-Benzyl-morpholin-2-one is used as a potential treatment for substance abuse and addiction due to its investigational role in modulating the neurokinin-1 receptor. This may help in reducing cravings and withdrawal symptoms, supporting the recovery process for individuals struggling with addiction.

InChI:InChI=1/C11H13NO2/c13-11-9-12(6-7-14-11)8-10-4-2-1-3-5-10/h1-5H,6-9H2

Upstream product

• 124948-51-2 (E)-2-(benzylideneamino)ethanol 
• 104-63-2 N-Benzylethanolamine 
• 770-37-6 2-(N-benzylidenamino)ethanol 
• 100-39-0 benzyl bromide 
• 101-32-6 N-benzyl-diethanolamine 
• 105-39-5 chloroacetic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 106-93-4 ethylene dibromide 
• 56-40-6 glycine 
• 5437-45-6 Benzyl bromoacetate 
• 131543-46-9 Glyoxal 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 120800-83-1 2-[Benzyl-(2-hydroxy-ethyl)-amino]-1-pyrrolidin-1-yl-ethanone 
• 118460-15-4 [(2-Acetoxy-ethyl)-benzyl-amino]-acetic acid methyl ester 
• 1375855-46-1 2-(benzyl(2-hydroxyethyl)amino)-N-(2-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthene]-2-yl)ethyl)acetamide 
• 4441-15-0 morpholin-2-one 
• 159706-87-3 4-benzyl-3-(4-fluorophenyl)morpholin-2-one 
• 503187-88-0 (6S)-6-Benzyl-morpholin-2-one 
• 120800-79-5 N-benzyl-N-(2-hydroxyethyl)glycine 
• 101-32-6 N-benzyl-diethanolamine 
• 73933-20-7 N-benzyl-2-hydroxymorpholine 
• 120800-81-9 N-Benzyl-2-[benzyl-(2-hydroxy-ethyl)-amino]-acetamide 
• 120800-82-0 {2-[Benzyl-(2-hydroxy-ethyl)-amino]-acetylamino}-acetic acid methyl ester 
• 120800-80-8 1-[Benzyl-(2-hydroxy-ethyl)-amino]-2-methyl-propan-2-ol 
• 118460-24-5 methyl 2-(benzyl(2-hydroxyethyl)amino)acetate 

Relevant academic research and scientific papers

Facile Access to the 12-Membered Macrocyclic Ligand PCTA and Its Derivatives with Carboxylate, Amide, and Phosphinate Ligating Functionalities

We describe a convenient synthetic pathway to access the 12-membered PCTA macrocycle, a polyaminocarboxylate ligand for which its M2+ and M3+ complexes are commonly associated with applications in biomedical diagnostics and radiother

Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using

Substituted 1,4,7-triazacyclononane-N,N′,N″-triacetic acid and 1,4,7,10-tetraazacyclcododecane-N,N′,N″,N′″-tetraacetic acid compounds with a pendant amino or hydroxyl group, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

Optimization of gefitinib analogues with potent anticancer activity

The interactions of gefitinib (Iressa) in EGFR are hydrogen bonding and van der Waals forces through quinazoline and aniline rings. However the morpholino group of gefitinib is poorly ordered due to its weak electron density. A series of novel piperazino analogues of gefitinib where morpholino group substituted with various piperazino groups were designed and synthesized. Most of them indicated significant anti-cancer activities against human cancer cell lines. In particular, compounds 52-54 showed excellent potency against cancer cells. Convergent synthetic approach has been developed for the synthesis of gefitinib intermediate which can lead to gefitinib as well as numerous analogues.

Organocatalytic ring-opening polymerization of morpholinones: New strategies to functionalized polyesters

The oxidative lactonization of N-substituted diethanolamines with the Pd catalyst [LPd(OAc)]22+[OTf-]2 generates N-substituted morpholin-2-ones. The organocatalytic ring-opening polymerization of N-acyl morpholin-2-ones occurs readily to generate functionalized poly(aminoesters) with N-acylated amines in the polyester backbone. The thermodynamics of the ring-opening polymerization depends sensitively on the hybridization of the nitrogen of the heterocyclic lactone. N-Acyl morpholin-2-ones polymerize readily to generate polymorpholinones, but the N-aryl or N-alkyl substituted morpholin-2-ones do not polymerize. Experimental and theoretical studies reveal that the thermodynamics of ring opening correlates to the degree of pyramidalization of the endocyclic N-atom. Deprotection of the poly(N-Boc-morpholin-2-one) yields a water-soluble, cationic polymorpholinone.

A rhodamine appended tripodal receptor as a ratiometric probe for Hg 2+ ions

A new rhodamine appended tripodal receptor 1 has been designed and synthesized. The receptor selectively recognizes Hg2+ ions in CH 3CN-water (4:1, v/v; 10 μM tris HCl buffer, pH 7.0) by displaying a ratiometric change in emission. Additionally, the visual detection is possible by a sharp change in color. The receptor shows in vitro detection of Hg 2+ ions in human cervical cancer (HeLa) cells.

Simple and efficient one pot synthetic protocol to construct morpholin-2-ones

A new one pot synthetic method to construct 3-substituted morpholine-2-one derivatives is presented. Amino acids refluxed with 1,2-dibromoethane and potassium carbonate in acetonitrile followed by treatment with benzyl bromide in same pot furnished the 3-

Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using

Substituted 1,4,7-triazacyclononane-N,N′,N″-triacetic acid and 1,4,7,10-tetraazacyclcododecane-N,N′,N″,N′″-tetraacetic acid compounds with a pendant amino or hydroxyl group, metal complexes thereof, compositions thereof, and methods of making and use in diagnostic imaging and treatment of cellular disorders.

Synthesis and evaluation of novel polyaminocarboxylate-based antitumor agents

Iron depletion, using iron chelators targeting transferrin receptor (TfR) and ribonucleotide reductase (RR), is proven to be effective in the treatment of cancer. We synthesized and evaluated novel polyaminocarboxylate-based chelators NETA, NE3TA, and NE3TA-Bn and their bifunctional versions C-NETA, C-NE3TA, and N-NE3TA for use in iron depletion tumor therapy. The cytotoxic activities of the novel polyaminocarboxylates were evaluated in the HeLa and HT29 colon cancer cell lines and compared to the clinically available iron depletion agent DFO and the frequently explored polyaminocarboxylate DTPA. All new chelators except C-NETA displayed enhanced cytotoxicities in both HeLa and HT29 cancer cells compared to DFO and DTPA. Incorporation of the nitro functional unit for conjugation to a targeting moiety into the two potent non-functionalized chelators NE3TA and NE3TA-Bn (C-NE3TA and N-NE3TA) was well-tolerated and resulted in a minimal decrease in cytotoxicity. Cellular uptake of C-NE3TA, examined using a confocal microscope, indicates that the chelator is taken up into HT29 cancer cells.

Disproportionation reactions from glyoxal and difunctional basic molecules

Glyoxal was reacted with basic difunctional molecules in order to study the disproportionation reaction.Symmetrical and unsymmetrical 1,2-diamines gave rise to piperazinones; their 1,3-diamine analogues yielded hexahydrodiazepinones; and β-aminoalcohols yielded morpholinones and hydroxyamino acids.Aminoamides gave the expected piperazinediones in low yields and no reaction was observed with diamides.The first step of the reaction consists of the formation of dihydroxy compounds, from which the more basic function assists the departure of OH, providing the expected more stable iminium ion.The observed regioselectivity is consistent with the relative basicities of the two functions; a 100percent regioselectivity is observed with aminoalcohols (giving way to morpholinones and not to amides), a good regiposelectivity with most of N-alkyl-N'-aryl-diamines and a rather low one with N-methyl-N'-ethyl- or N-methyl-N'-p-methoxyphenyl-diamines.Geometry factors were related to the better yield obtained with 1,2-diamines compared with 1,3-diamines.The mechanism was investigated.When deutared glyoxal and diamines were reacted in D2O, incorporation of deuterium was observed, in accordance with the formation of an enolate in the course of the oxidoreduction.The low reactivity of aminoamides and the observed regioselectivities could be related to both the weak basicity of the function that is supposed to allow the formation of the iminium ion and the basicity of the other function that accepts a positive charge and which, if too weak, impedes the reaction because of the instability of the intermediate iminium ion. glyoxal / disproportionation rules / basic difunctional molecules

Nucleophilic Ring-Opening Reactions of Morpholin-2-ones. A Resolution of dl-(Secondary-alkyl)amines

The alcoholysis of morpholin-2-ones yielded an equilibrium mixture of morpholin-2-one and the corresponding hydroxy ester.The equilibrium constants for the methanolysis of several sustituted morpholin-2-ones were determined.Treatment of optically active morpholin-2-ones with (secondary-alkyl)amines resulted in stereoselective ring opening to afford hydroxy amides with up to 30percent de.Hydrolysis of one such hydroxy amide regenerated the optically active (secondary-alkyl)amine and the morpholin-2-one.