5807-09-0

Usage

Uses

Used in Pharmaceutical Industry:
4-morpholin-4-ylbutanoic acid is used as a therapeutic agent for the treatment of neurological and psychiatric disorders such as anxiety, depression, and epilepsy. Its potential anti-convulsant and anxiolytic properties make it a promising candidate for these applications.
Used in Drug Addiction Treatment:
4-morpholin-4-ylbutanoic acid is used as a potential drug candidate for the treatment of drug addiction and withdrawal symptoms. Its interaction with GABAergic signaling pathways may help alleviate the symptoms associated with addiction and withdrawal.
Used in Neurological Research:
4-morpholin-4-ylbutanoic acid is used as a research tool to study the role of GABAergic signaling pathways in the central nervous system. Its potential as a novel and effective therapeutic agent targeting these pathways makes it of interest to researchers and pharmaceutical companies for further investigation and development.

InChI:InChI=1/C8H15NO3/c10-8(11)2-1-3-9-4-6-12-7-5-9/h1-7H2,(H,10,11)

Upstream product

• 5471-53-4 methyl 4-morpholinobutanoate 
• 88217-57-6 3-morpholin-4-ylpropionic acid ethyl ester 

Downstream Products

• 1620517-08-9 4-morpholino-N-(3-(5-p-tolyl-1,3,4-oxadiazol-2-yl)phenyl)butanamide 
• 252936-34-8 N-[2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]-4-morpholin-4-ylbutanamide 

Relevant academic research and scientific papers

Drugs derived from cannabinoids. 2. Basic esters of nitrogen and carbocyclic analogs

Various basic esters of nitrogen (2) and carbocyclic (3 and 4) analogs of cannabinoids were synthesized using dicyclohexylcarbodiimide in methylene chloride. The compounds in the three series were studied in selected pharmacological tests in mice, rats, dogs, and cats. It was shown that making the basic ester from the phenol retains biological activity and can lead to a greater selectivity of action, particularly the antinociceptive activity. The most interesting esters were 5, 6, 10, and 14 in the nitrogen analogs series and 19 and 20 in the carbocyclic series. Compound 5 was more potent than codeine in the writhing, hot plate, and tail flick tests and is at present undergoing clinical testing. Compound 20 was very potent in the mouse audiogenic seizure test and is of interest as an anticonvulsant agent.

QSAR and molecular docking studies of the inhibitory activity of novel heterocyclic GABA analogues over GABA-AT

We have previously reported the synthesis, in vitro and in silico activities of new GABA analogues as inhibitors of the GABA-AT enzyme from Pseudomonas fluorescens, where the nitrogen atom at the γ-position is embedded in heterocyclic scaffolds. With the goal of finding more potent inhibitors, we now report the synthesis of a new set of GABA analogues with a broader variation of heterocyclic scaffolds at the γ-position such as thiazolidines, methyl-substituted piperidines, morpholine and thiomorpholine and determined their inhibitory potential over the GABA-AT enzyme from Pseudomonas fluorescens. These structural modifications led to compound 9b which showed a 73% inhibition against this enzyme. In vivo studies with PTZ-induced seizures on male CD1 mice show that compound 9b has a neuroprotective effect at a 0.50 mmole/kg dose. A QSAR study was carried out to find the molecular descriptors associated with the structural changes in the GABA scaffold to explain their inhibitory activity against GABA-AT. Employing 3D molecular descriptors allowed us to propose the GABA analogues enantiomeric active form. To evaluate the interaction with Pseudomonas fluorescens and human GABA-AT by molecular docking, the constructions of homology models was carried out. From these calculations, 9b showed a strong interaction with both GABA-AT enzymes in agreement with experimental results and the QSAR model, which indicates that bulky ligands tend to be the better inhibitors especially those with a sulfur atom on their structure.

Development of a series of bis-triazoles as G-quadruplex ligands

Maintenance of telomeres-specialized complexes that protect the ends of chromosomes-is provided by the enzyme complex telomerase, which is a key factor that is activated in more than 80% of cancer cells, but absent in most normal cells. Targeting telomere maintenance mechanisms could potentially halt tumour growth across a broad spectrum of cancer types. Telomeric ends of chromosomes consist of noncoding repeat sequences of guanine-rich DNA. These G-rich ends can fold into structures called G-quadruplexes. Stabilization of G-quadruplexes by small binding molecules called G4 ligands can prevent telomerase enzyme from maintaining telomere integrity in cancer cells. G-quadruplexes can exist in other parts of the genome too, especially within promoter sequences of oncogenes, and also be interesting drug targets. Here, we describe the development of a new series of novel bis-triazoles, designed to stabilize G-quadruplex structures selectively as G4 ligands. FRET assays showed two compounds to be moderately effective G4 binders, with particular affinity for the quadruplex formed by the Hsp90a promoter sequence, and good selectivity for G-quadruplex DNA vs. duplex DNA. However, CD spectroscopy failed to provide any information about the folding topology of the human telomeric G-quadruplex resulting from its interaction with one of the ligands. All the new ligands showed potent cell growth inhibitory properties against human colon and pancreatic cancer cell lines, as evidenced by the MTT assay; notably, they were more potent against cancer cells than in fetal lung fibroblasts. Docking studies were performed to rationalize the affinity of these ligands for binding to the telomeric parallel G-quadruplex DNA.

3-UREIDOISOQUINOLIN-8-YL DERIVATIVES

The invention relates to 3-ureidoisoquinolin-8-yl derivatives of formula I I wherein R is alkyl, haloalkyl or cyclopropyl; R 2 is H, halogen, pyridazin-4-yl, pyrimidin-5-yl or an optionally substituted pyridin-3-yl, pyridin-4-yl or phenyl group; R 3 is alkyl, alkynyl, aminoalkyl, carbamoylalkyl, methylcarbamoylalkyl, alkoxy, haloalkoxy, alkynyloxy, (4-hydroxybut-2-yn-1-yl)oxy, (4-aminobut-2-yn-1-yl)oxy, dimethylaminoalkoxy, carbamoylalkoxy, alkylamino, cycloalkyl, cycloalkylalkyl, cycloalkylalkoxy, hydroxyalkyl, hydroxyalkoxy, alkoxyalkyl, alkoxyalkoxy, carboxyalkyl, carboxyalkoxy, alkoxycarbonylalkoxy, aryl, heteroaryl, benzyl, benzyloxy, 2-cyanoethoxy, 2,3-dihydroxypropoxy, 3,4-dihydroxybutoxy, -CH 2 R a, -CH 2 CH 2 R b, -(CH 2 ) n -C(O)O-R d, -(CH 2 ) n -N(R c )C(O)O-R d, -O-(CH 2 ) n -N(R c )C(O)O-R d, -(CH 2 ) n -R e or -O-(CH 2 ) n -R e; R a is cyano, acetylamino or N,N-dimethylamino; R b is cyano or carbamoyl; R c is H or methyl; R d is alkyl; R e is pyrrolidin-1-yl, piperidin-1-yl, piperidin-3-yl, morpholin-1-yl, 2-oxopyrrolidin-1-yl, 5-oxopyrrolidin-2-yl, 2,5-dioxopyrrolidin-1-yl, 2-oxoimidazolidin-1-yl, 4-(tert-butoxycarbonyl)piperazin-1-yl, 4-(aminomethyl)cyclohexyl or heteroaryl; R 4 is H or methyl; and to the salts of such compounds. These compounds are useful for the prevention or the treatment of bacterial infections.

NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS

The present invention provides compounds of formula (I) and compositions thereof, methods of making them, and methods of using them to modulate alpha7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other things, neurological, psychiatric and/or inflammatory system.

Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication

Improved anesthesia methods comprising pretreating a patient to be anesthetized with a benzopyran of formula I STR1 wherein, in the C ring, X is NR1, S, CH2 or STR2 R1 is hydrogen, loweralkyl, loweralkenyl, loweralkynyl, loweralkanoyl, cycloalkyloweralkyl, cycloalkylloweralkanoyl, cycloalkyl, haloloweralkyl, haloloweralkenyl, phenylloweralkyl, phenyloweralkenyl or phenyloweralkylnyl; m is an integer from 0 to 3, n is an integer from 0 to 3 and n + m = 2 or 3; or the C ring is quinuclidine ring STR3 R2 is loweralkyl; R3 is hydrogen or STR4 wherein Y is a straight or branched chain alkylene group having from one to eight carbon atoms, a is an integer from 1 to 4, b is an integer from 1 to 4, Z is CH2, O, S or NR6, R6 being hydrogen or loweralkyl, with the limitation that when Z is O, S or NR5, the sum of a and b is 3 or 4, and R5 is hydrogen or loweralkyl; R4 is C1 -C20 straight or branched chain alkyl, cycloalkyl, or STR5 wherein Y is a straight or branched chain alkylene group having from one to ten carbon atoms, and each R7, R8 and R9 are the same or different members of the group consisting of hydrogen, halo, trifluoromethyl or loweralkyl; and the pharmaceutically acceptable salts thereof, with the limitation that when X is STR6 m = 2 and n = 2, R3 cannot be hydrogen.