2933-75-7

Usage

Structure

consists of a 2-methoxyphenyl group attached to an amino ethanol group

Uses

intermediate in the synthesis of pharmaceuticals and organic compounds, solvent, raw material for other chemical production, potential applications in drug development

Properties

readily undergoes chemical reactions, may pose health and safety risks if not handled and stored properly

InChI:InChI=1/C9H13NO2/c1-12-9-5-3-2-4-8(9)10-6-7-11/h2-5,10-11H,6-7H2,1H3

Upstream product

• 75-21-8 oxirane 
• 90-04-0 2-methoxy-phenylamine 
• 107-07-3 2-chloro-ethanol 
• 107-21-1 ethylene glycol 
• 1836-62-0 2-(2-methoxy-phenoxy)-ethylamine 

Downstream Products

• 3367-49-5 1,4-bis-(2-methoxy-phenyl)-piperazine 
• 1606589-17-6 C₁₈H₂₉NO₃Si 
• 1606589-28-9 C₁₂H₁₅NO₃ 
• 1606589-52-9 4-hydroxy-1-(2-methoxyphenyl)-3-methylenepyrrolidin-2-one 
• 1606589-40-5 C₁₂H₁₃NO₃ 

Relevant academic research and scientific papers

Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics

We report the first examples of radical cation Smiles rearrangements. A series of aryloxy alkylamines underwent spontaneous reaction, with the amino group displacing theipso-alkoxy group through substitution, at ambient temperature and under photoactivation by visible light in the presence of an acridinium catalyst (5 mol%). The study was extended to 3-(2-methoxyphenyl)propan-1-amine derivatives, which lack an appropriateipsoleaving group. Here, efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines.

β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction

Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.

Bis-aryl urea derivatives as potent and selective LIM kinase (Limk) inhibitors

The discovery/optimization of bis-aryl ureas as Limk inhibitors to obtain high potency and selectivity and appropriate pharmacokinetic properties through systematic SAR studies is reported. Docking studies supported the observed SAR. Optimized Limk inhibitors had high biochemical potency (IC50 400-fold), potent inhibition of cofilin phosphorylation in A7r5, PC-3, and CEM-SS T cells (IC50 1 μM), and good in vitro and in vivo pharmacokinetic properties. In the profiling against a panel of 61 kinases, compound 18b at 1 μM inhibited only Limk1 and STK16 with ≥80% inhibition. Compounds 18b and 18f were highly efficient in inhibiting cell-invasion/migration in PC-3 cells. In addition, compound 18w was demonstrated to be effective on reducing intraocular pressure (IOP) on rat eyes. Taken together, these data demonstrated that we had developed a novel class of bis-aryl urea derived potent and selective Limk inhibitors.

INDAZOLEPROPIONIC ACID AMIDE COMPOUND

Disclosed is a compound which is useful in preventing and treating cardiac arrhythmia such as atrial fibrillation. A compound represented by formula (1) or a pharmaceutically acceptable salt of the same. In formula (1), ring X represents benzene or pyridine; R1 represents an optionally substituted alkyl group; R2 represents an optionally substituted aryl group, an optionally substituted heterocyclic group, an optionally substituted arylalkyl group or an optionally substituted heterocyclic group-substituted alkyl group; R3, R4, R5, R6, R7, R8 and R9 represent each hydrogen or an alkyl group, provided that R3 and R5 may be bonded to each other to form, together with the carbon atom adjacent thereto, a cycloalkyl group; and m represents 0 or 1.