24152-96-3

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL is used as a pharmaceutical intermediate for its role in the synthesis of various medications, including antiviral and anticancer drugs. It serves as a key component in the development of new therapeutic agents, contributing to the advancement of medical treatments.
Used in Medication Synthesis:
2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL is used as a building block in the creation of other compounds, facilitating the design and production of novel pharmaceuticals. Its unique structure allows for versatile chemical reactions, making it an essential tool in the medicinal chemistry field for the development of innovative drugs.
Used in Antiviral and Anticancer Drug Development:
2-AMINO-1-MORPHOLIN-4-YL-ETHANONE HCL is utilized in the formulation of antiviral and anticancer medications due to its potential therapeutic applications. Its presence in these drugs aids in targeting and combating viral and cancerous cells, offering hope for improved treatment options in these areas of medicine.

InChI:InChI=1/C6H12N2O2.ClH/c7-5-6(9)8-1-3-10-4-2-8;/h1-5,7H2;1H

Upstream product

• 864528-04-1 2-azido-1-(morpholin-4-yl)ethan-1-one 
• 114703-81-0 (2-morpholin-4-yl-2-oxo-ethyl)-carbamic acid tert-butyl ester 

Downstream Products

• 25439-22-9 N-(2-morpholin-4-yl-2-oxo-ethyl)-2-phenyl-acetamide 
• 58792-09-9 4-[5-(4-methoxy-phenoxymethyl)-[1,2,3]thiadiazole-4-carbonyl]-morpholine 
• 58792-07-7 4-[5-(3,4-dichloro-phenoxymethyl)-[1,2,3]thiadiazole-4-carbonyl]-morpholine 
• 1251933-13-7 2-(5-chloro-6-methyl-3-(2-morpholino-2-oxoethylamino)-2-oxopyrazin-1(2H)-yl)-2-phenylacetic acid methyl ester 
• 1356556-40-5 (1-(2,6-diisopropylphenyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-65-4 (R)-(1-(1-phenylethyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-32-5 (1-(4-methoxyphenyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-38-1 (1-(4-nitrophenyl)-1H-imidazol-4-yl)(morpholino)methanone 
• 1356556-35-8 ethyl 4-(4-(morpholine-4-carbonyl)-1H-imidazol-1yl)benzoate 
• 1355040-42-4 methyl 3-[(2,4-dichlorobenzoyl)-(2-morpholino-2-oxo-ethyl)amino]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate 
• 1355040-41-3 methyl 3-[(4-chlorobenzoyl)-(2-morpholino-2-oxo-ethyl)amino]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate 
• 1355040-43-5 methyl 5-(3,3-dimethylbut-1-ynyl)-3-[(4-methylbenzoyl)-(2-morpholino-2-oxo-ethyl)amino]thiophene-2-carboxylate 

Relevant academic research and scientific papers

Synthesis and biological evaluation of potential inhibitors of the cysteine proteases cruzain and rhodesain designed by molecular simplification

Analogues of 8-chloro-N-(3-morpholinopropyl)-5H-pyrimido[5,4-b]indol-4-amine 1, a known cruzain inhibitor, were synthesized using a molecular simplification strategy. Five series of analogues were obtained: indole, pyrimidine, quinoline, aniline and pyrrole derivatives. The activity of the compounds was evaluated against the enzymes cruzain and rhodesain as well as against Trypanosoma cruzi amastigote and trypomastigote forms. The 4-aminoquinoline derivatives showed promising activity against both enzymes, with IC50values ranging from 15 to 125?μM. These derivatives were selective inhibitors for the parasitic proteases, being unable to inhibit mammalian cathepsins B and S. The most active compound against cruzain (compound 5a; IC50?=?15?μM) is considerably more synthetically accessible than 1, while retaining its ligand efficiency. As observed for the original lead, compound 5a was shown to be a competitive enzyme inhibitor. In addition, it was also active against T. cruzi (IC50?=?67.7?μM). Interestingly, the pyrimidine derivative 4b, although inactive in enzymatic assays, was highly active against T. cruzi (IC50?=?3.1?μM) with remarkable selectivity index (SI?=?128) compared to uninfected fibroblasts. Both 5a and 4b exhibit drug-like physicochemical properties and are predicted to have a favorable ADME profile, therefore having great potential as candidates for lead optimization in the search for new drugs to treat Chagas disease.

Selective Allosteric Antagonists for the G Protein-Coupled Receptor GPRC6A Based on the 2-Phenylindole Privileged Structure Scaffold

G protein-coupled receptors (GPCRs) represent a biological target class of fundamental importance in drug therapy. The GPRC6A receptor is a newly deorphanized class C GPCR that we recently reported for the first allosteric antagonists based on the 2-arylindole privileged structure scaffold (e.g., 1-3). Herein, we present the first structure-activity relationship study for the 2-arylindole antagonist 3, comprising the design, synthesis, and pharmacological evaluation of a focused library of 3-substituted 2-arylindoles. In a FRET-based inositol monophosphate (IP1) assay we identified compounds 7, 13e, and 34b as antagonists at the GPRC6A receptor in the low micromolar range and show that 7 and 34b display >9-fold selectivity for the GPRC6A receptor over related GPCRs, making 7 and 34b the most potent and selective antagonists for the GPRC6A receptor reported to date.

Inhibitors of Cyclic AMP Phosphodiesterase. 4. Synthesis and Evaluation of Potential Prodrugs of Lixazinone (N-Cyclohexyl-N-methyl-4quinazolin-7-yl)oxy>butyramide, RS-82856)

The cyclic AMP phosphodiesterase (cAMP PDE) inhibitor and cardiotonic agent lixazinone (N-cyclohexyl-N-methyl-4-quinazolin-7-yl)oxy>butyramide, RS-82856, 1) and its acid and base addition salts were found to be insufficiently soluble in formulations suitable for intravenous administration.These results prompted an investigation into potential prodrugs with enhanced aqueous solubility designed to deliver 1 by three distinct mechanisms: (1) decarboxylation of α-carboxamides; (2) hydrolytic loss of a solubilizing N-1-(acyloxy)methyl or (N,N-dialkylamino)methyl moiety; or (3) intramolecular closure of a guanidino ester or amide.The target compounds were evaluated as delivery systems for 1 by three criteria: (1) chemical conversion rate to 1 under physiological conditions; (2) inhibition of type IV cAMP PDE at a fixed time point; and (3) in vivo inotropic activity in anesthetized dogs by both intravenous and oral administration.Release of 1 from 4a (series 1) was found to be too slow to be of value as prodrug of 1, since decarboxylation could be induced only by strong acid, conditions under which hydrolytic ring opening was found to severely compete.Conversely, 1 was released too readily on exposure of (N,N-dialkylamino)methyl derivatives such as 8d (series 2) to physiological conditions, although no large increase in aqueous solubility was realized.Finally, both the physicochemical and in vitro studies indicated that ring closure of the guanidinium esters and amides 17a-k (series 3) to 1 was quantitative and pH- and time-dependent, suggesting the possibility of delivery of the open, water-soluble prodrug form, followed by closure to 1 in plasma.Detailed examination of these agents in vivo, however, demonstrated that only those compounds that rapidly cyclized to 1, as measured by plasma levels of 1, exhibited inotropic activity, indicating that the open prodrug form was not efficiently absorbed upon oral administration.