40987-24-4

Usage

Uses

Used in Pharmaceutical Industry:
(4-Benzyl-1,4-oxazinan-2-yl)methanol is used as an intermediate in the synthesis of various antidepressants and protein kinase inhibitors. Its unique chemical structure allows for the development of new and effective medications that can help treat a range of mental health disorders and conditions related to the dysregulation of protein kinases.
Used in Chemical Industry:
(4-Benzyl-1,4-oxazinan-2-y)methanol is also utilized as a key intermediate in the preparation of other complex organic compounds. Its versatility and unique structure make it a valuable building block for the synthesis of a wide range of chemical products, including specialty chemicals, pharmaceuticals, and advanced materials.

InChI:InChI=1/C12H17NO2/c14-10-12-9-13(6-7-15-12)8-11-4-2-1-3-5-11/h1-5,12,14H,6-10H2/p+1/t12-/m0/s1

Upstream product

• 40987-25-5 N-benzyl-2-chloromethylmorpholine 
• 61636-32-6 5S-N-Benzylmorpholin-3-one 
• 174560-84-0 1-chloro-3-[(2-hydroxyethyl)(phenylmethyl)amino]-2-propanol 
• 104-63-2 N-Benzylethanolamine 
• 769087-80-1 4-benzylmorpholine-2-carboxylic acid 

Downstream Products

• 135065-69-9 tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate 
• 385814-36-8 4-(phenylmethyl)-2-morpholinemethanol methanesulfonate 
• 144053-98-5 2-(hydroxymethyl)morpholine hydrochloride 
• 874815-98-2 4-benzyl-2-(piperazin-1-ylmethyl)morpholine 
• 635698-80-5 tert-butyl 4-((4-benzylmorpholin-2-yl)methyl)piperazine-1-carboxylate 

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.

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 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.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

The present application relates to cannabinoid receptor ligands of formula (I) wherein X1, A1, Rx, R2, R3, R4, and z are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions.

Concise synthesis of (S)-N-BOC-2-hydroxymethylmorpholine and (S)-N-BOC-morpholine-2-carboxylic acid

(Chemical Equation Presented) An operationally simple synthesis of N-BOC-2-hydroxymethylmorpholine (1) and N-BOC-morpholine-2-carboxylic acid (2) from epichlorohydrin has been developed. No chromatography is required in the processing, which allows high p