943442-96-4

Usage

Uses

Used in Pharmaceutical Industry:
((R)-4-benzylmorpholin-2-yl)methanol is used as a chiral building block for the preparation of various pharmaceuticals. Its unique chiral structure and versatile synthetic applications make it highly useful in the development of new drugs.
Used in Agrochemical Industry:
((R)-4-benzylmorpholin-2-yl)methanol is used as a chiral building block in the synthesis of agrochemicals. It contributes to the development of new agricultural chemicals with improved efficacy and selectivity.
Used in Chemical Research:
((R)-4-benzylmorpholin-2-yl)methanol is used as a chiral ligand in asymmetric catalysis. It plays a crucial role in enhancing the selectivity and efficiency of various chemical reactions, leading to the production of enantiomerically pure compounds.
Used in the Production of Chiral Auxiliaries and Ligands:
((R)-4-benzylmorpholin-2-yl)methanol serves as a starting material in the synthesis of chiral auxiliaries and ligands. These compounds are essential in various asymmetric reactions, facilitating the formation of specific enantiomers with high selectivity.

InChI:InChI=1S/C12H17NO2/c14-10-12-9-13(6-7-15-12)8-11-4-2-1-3-5-11/h1-5,12,14H,6-10H2/t12-/m1/s1

Upstream product

• 40987-25-5 N-benzyl-2-chloromethylmorpholine 
• 61636-32-6 5S-N-Benzylmorpholin-3-one 
• 104-63-2 N-Benzylethanolamine 
• 174560-84-0 1-chloro-3-[(2-hydroxyethyl)(phenylmethyl)amino]-2-propanol 
• 67843-74-7 (S)-epichlorohydrin 
• 148638-80-6 N-benzyl-N-(tert-butoxycarbonyl)-N-<2(S),3-dihydroxypropyl>amine 
• 1022915-29-2 (R)-1-chloro-3-[(2-hydroxyethyl)(phenylmethyl)amino]-2-propanol 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 100-52-7 benzaldehyde 
• 135065-72-4 (S)-N-benzyl-3-chloroacetamidopropane-1,2-diol 
• 148638-81-7 Methanesulfonic acid (S)-2-(benzyl-tert-butoxycarbonyl-amino)-1-methanesulfonyloxymethyl-ethyl ester 
• 148638-79-3 N-benzyl-N-(tert-butoxycarbonyl)-N-amine 
• 148638-82-8 Acetic acid (R)-3-benzyl-2-oxo-oxazolidin-5-ylmethyl ester 
• 148638-77-1 N-Benzyl-2-chloro-N-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-acetamide 

Relevant academic research and scientific papers

Synthesis and Initial Characterization of a Selective, Pseudo-irreversible Inhibitor of Human Butyrylcholinesterase as PET Tracer

The enzyme butyrylcholinesterase (BChE) represents a promising target for imaging probes to potentially enable early diagnosis of neurodegenerative diseases like Alzheimer's disease (AD) and to monitor disease progression in some forms of cancer. In this study, we present the design, facile synthesis, in vitro and preliminary ex vivo and in vivo evaluation of a morpholine-based, selective inhibitor of human BChE as a positron emission tomography (PET) tracer with a pseudo-irreversible binding mode. We demonstrate a novel protecting group strategy for 18F radiolabeling of carbamate precursors and show that the inhibitory potency as well as kinetic properties of our unlabeled reference compound were retained in comparison to the parent compound. In particular, the prolonged duration of enzyme inhibition of such a morpholinocarbamate motivated us to design a PET tracer, possibly enabling a precise mapping of BChE distribution.

Radiosynthesis and evaluation of 18F-labeled dopamine D4-receptor ligands

Introduction: The dopamine D4 receptor (D4R) has attracted considerable attention as potential target for the treatment of a broad range of central nervous system disorders. Although many efforts have been made to improve the performance of putative radioligand candidates, there is still a lack of D4R selective tracers suitable for in vivo PET imaging. Thus, the objective of this work was to develop a D4-selective PET ligand for clinical applications. Methods: Four compounds based on previous and new lead structures were prepared and characterized with regard to their D4R subtype selectivity and predicted lipophilicity. From these, 3-((4-(2-fluorophenyl)piperazin-1-yl)methyl)-1H-pyrrolo[2,3-b]pyridine I and (S)-4-(3-fluoro-4-methoxybenzyl)-2-(phenoxymethyl)morpholine II were selected for labeling with fluorine-18 and subsequent evaluation by in vitro autoradiography to assess their suitability as D4 radioligand candidates for in vivo imaging. Results: The radiosynthesis of [18F]I and [18F]II was successfully achieved by copper-mediated radiofluorination with radiochemical yields of 7% and 66%, respectively. The radioligand [18F]II showed specific binding in areas where D4 expression is expected, whereas [18F]I did not show any uptake in distinct brain regions and exhibited an unacceptable degree of non-specific binding. Conclusions: The compounds studied exhibited high D4R subtype selectivity and logP values compatible with high brain uptake, but only ligand [18F]II showed low non-specific binding and is therefore a good candidate for further evaluation. Advances in knowledge: The discovery of new lead structures for high-affinity D4 ligands opens up new possibilities for the development of suitable PET-radioligands. Implications for patient: PET-imaging of dopamine D4-receptors could facilitate understanding, diagnosis and treatment of neuropsychiatric and neurodegenerative diseases.

Novel Hydrazinone-substituted Pyrimidine Derivatives and Use Thereof

The present invention relates to a pyrimidine derivative substituted with novel hydrazine or a pharmaceutically acceptable salt thereof, and to a pharmaceutical composition for inhibiting c-Met tyrosine kinase activity and to a pharmaceutical composition for preventing or treating hyperproliferative disorders, which comprise same as an active ingredient. The present invention can be effectively used as a treatment agent for various hyperproliferative disorders related to excessive cell proliferation and growth caused by abnormal kinase activity, such as cancer, psoriasis, rheumatoid arthritis, and diabetic retinopathy by efficiently inhibiting c-Met tyrosine kinase activity.

Development of the First Generation of Disulfide-Based Subtype-Selective and Potent Covalent Pyruvate Dehydrogenase Kinase 1 (PDK1) Inhibitors

Pyruvate dehydrogenase kinases (PDKs) are overexpressed in most cancer cells and are responsible for aberrant glucose metabolism. We previously described bis(4-morpholinyl thiocarbonyl)-disulfide (JX06, 16) as the first covalent inhibitor of PDK1. Here, on the basis of the scaffold of 16, we identify two novel types of disulfide-based PDK1 inhibitors. The most potent analogue, 3a, effectively inhibits PDK1 both at the molecular (kinact/Ki = 4.17 × 103 M-1 s-1) and the cellular level (down to 0.1 μM). In contrast to 16, 3a is a potent and subtype-selective inhibitor of PDK1 with >40-fold selectivity for PDK2-4. 3a also significantly alters glucose metabolic pathways in A549 cells by decreasing ECAR and increasing ROS. Moreover, in the xenograft models, 3a shows significant antitumor activity with no negative effect to the mice weight. Collectively, these data demonstrate that 3a may be an excellent lead compound for the treatment of cancer as a first-generation subtype-selective and covalent PDK1 inhibitor.

Novel Triazolopyrazine Derivatives and Use Thereof

The present invention relates to novel triazolopyrazine derivatives or a pharmaceutically acceptable salt, and a pharmaceutical composition for inhibiting c-Met tyrosine kinase activity and a pharmaceutical composition for preventing or treating hyperproliferative disorders, containing the same as active ingredients. The present invention effectively inhibits c-Met tyrosine kinase activity, thereby being able to be useful as a drug for various hyperproliferative disorders such as cancers, psoriasis, rheumatoid arthritis, diabetic retinitis, etc. related to excessive cell proliferation and growth by abnormal kinase activation.

Discovery of substituted pyrazol-4-yl pyridazinone derivatives as novel c-Met kinase inhibitors

A series of pyridazin-3-one substituted with morpholino-pyrimidine derivatives was synthesized and evaluated as tyrosine kinase inhibitors against c-Met enzyme, and anti-proliferative activities of Hs746T human gastric cancer cell line. Most of compounds exhibited good biological activity, while compound 10, 12a, 14a displayed excellent c-Met enzyme inhibitory activities and Hs746T cell-based activities.

NOVEL TRIAZOLOPYRAZINE DERIVATIVE AND USE THEREOF

The present invention relates to a novel triazolopyrazine derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing the same as an active ingredient for preventing or treating hyper proliferative disorder. The present invention can be useful as a therapeutic agent for various hyper proliferative disorders associated with excessive cell proliferation and growth caused by abnormal kinase activity, such as cancer, psoriasis, rheumatoid arthritis, and diabetic retinopathy, by efficiently inhibiting c-Met tyrosine kinase activity.

MORPHOLINO COMPOUNDS, USES AND METHODS

The invention relates to morpholino-derivatives according to Formula (I) or stereoisomers or pharmaceutically acceptable salts or solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7/s

Discovery of substituted 6-pheny-3H-pyridazin-3-one derivatives as novel c-Met kinase inhibitors

We report a series of phenyl substituted pyridazin-3-ones substituted with morpholino-pyrimidines. The SAR of the phenyl was explored and their c-Met kinase and cell-based inhibitory activity toward c-Met driven cell lines were evaluated. Described herein

NOVEL PYRIMIDINE DERIVATIVES, PREPARATION THEREOF, AND PHARMACEUTICAL USE THEREOF AS AKT(PKB) PHOSPHORYLATION INHIBITORS

The present invention relates to novel chemical compounds derived from pyrimidines, to the method for preparing same, to the novel intermediates obtained, to the use thereof as drugs, to the pharmaceutical compositions containing same, and to the therapeutic use thereof as AKT inhibitors.