91298-74-7

Usage

Uses

(1S)-2-Methoxy-1-phenylethylamine is an intermediate for G700620.

InChI:InChI=1/C9H13NO/c1-11-7-9(10)8-5-3-2-4-6-8/h2-6,9H,7,10H2,1H3/t9-/m1/s1

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 74-88-4 methyl iodide 
• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 
• 860304-24-1 N,N-diallyl-N-[(1R)-2-methoxy-1-phenylethyl]amine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 875-74-1 (R)-phenylglycine 
• 860304-23-0 (R)-2-N,N-diallylamino-2-phenylethanol 

Downstream Products

• 104942-87-2 R(-)-N-(1-phenyl-2-methoxyethyl)-N-trimethylsilylmethylamine 
• 139224-99-0 (S)-((R)-2-Methoxy-1-phenyl-ethylamino)-p-tolyl-acetonitrile 
• 137029-96-0 ((R)-2-Methoxy-1-phenyl-ethyl)-[4-(2-undecyl-[1,3]dioxolan-2-yl)-but-(E)-ylidene]-amine 
• 159171-45-6 (R)-N-ethylidene-2-methoxy-1-phenylethylamine 
• 159116-88-8 (R,E)-N-heptylidene-2-methoxy-1-phenylethanamine 
• 159116-89-9 ((R)-2-Methoxy-1-phenyl-ethyl)-[3-methylsulfanyl-prop-(E)-ylidene]-amine 
• 159116-91-3 4-[(E)-(R)-2-Methoxy-1-phenyl-ethylimino]-butyric acid tert-butyl ester 
• 159116-90-2 [2-Benzyloxy-eth-(E)-ylidene]-((R)-2-methoxy-1-phenyl-ethyl)-amine 
• 159116-86-6 [2-Cyclohexyl-eth-(E)-ylidene]-((R)-2-methoxy-1-phenyl-ethyl)-amine 
• 204974-19-6 (1R,2S)-2-Ethyl-1-((R)-2-methoxy-1-phenyl-ethylamino)-cyclopropanecarbonitrile 
• 204974-20-9 (1S,2R)-2-Ethyl-1-((R)-2-methoxy-1-phenyl-ethylamino)-cyclopropanecarbonitrile 
• 204973-82-0 (1R,2S)-1-((R)-2-Methoxy-1-phenyl-ethylamino)-2-methyl-cyclopropanecarbonitrile 
• 208844-35-3 N-[(1R)-2-methoxy-1-phenylethyl]-4-hexynamide 
• 252334-54-6 (R)-(E)-N-Butylidene-2-methoxy-1-phenylethylamine 

Relevant academic research and scientific papers

Monofluoroalkene-Isostere as a 19F NMR Label for the Peptide Backbone: Synthesis and Evaluation in Membrane-Bound PGLa and (KIGAKI)3

Solid-state 19F NMR is a powerful method to study the interactions of biologically active peptides with membranes. So far, in labelled peptides, the 19F-reporter group has always been installed on the side chain of an amino acid. Given the fact that monofluoroalkenes are non-hydrolyzable peptide bond mimics, we have synthesized a monofluoroalkene-based dipeptide isostere, Val-Ψ[(Z)-CF=CH]-Gly, and inserted it in the sequence of two well-studied antimicrobial peptides: PGLa and (KIGAKI)3 are representatives of an α-helix and a β-sheet. The conformations and biological activities of these labeled peptides were studied to assess the suitability of monofluoroalkenes for 19F NMR structure analysis.

Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

A base-induced dearomative [2,3] sigmatropic rearrangement of amino acid ester-derived ammonium salts followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters. The reaction of azetidine-2-carboxylic acid-derived ammonium salt, (1S,2S,1′R)-3b, proceeded with a perfect N-to-C chirality transfer to afford α-(ortho-vinylphenyl)azetidine-2-carboxylic acid ester, (R)-5 (99% ee). On the other hand, the reaction of glycine-derived ammonium salt (R)-6a, which involves an efficient chirality transfer from a chiral benzylic carbon to an α-carbon of an ester carbonyl giving the optically active α-(ortho-vinylphenyl)glycine ester, (R)-8a (85% ee), was demonstrated. Although this dearomative [2,3] rearrangement followed by 1,4-elimination has limitations with regard to the structures of the substrates, our method provides unique access to substituted α-arylamino acid derivatives.

Thienopyrimidine derivative, preparation method thereof and application thereof in medicines

The invention provides a thienopyrimidine derivative, a preparation method thereof and an application thereof in medicines. Specifically, the invention relates to a compound represented by a formula I, wherein the radicals are defined in the description. The compound is effective tyrosine kinase inhibitors in one category, and is particularly suitable for being used as an EGFR and/or HER2 inhibitor.

Structure-activity study leading to identification of a highly active thienopyrimidine based EGFR inhibitor

Based on the thieno[2,3-d]pyrimidine scaffold, a series of new 4-amino-6-aryl thienopyrimidines have been prepared and evaluated as EGFR tyrosine kinase inhibitors. The in vitro activity was found to depend strongly on the substitution pattern in the 6-aryl ring, the stereochemistry, and the basicity at the secondary 4-amino group. A stepwise optimization by combination of active fragments led to the discovery of three structures with EGFR IC 50 50 of 0.3 nM towards EGFR and its mutants L858R and L861Q. Studies using human cancer cell lines and an EGFR-L858R reporter cell system revealed good cellular potency, verifying the identified thienopyrimidines as promising lead structures.

Titanium-mediated cross-coupling reactions of imines with ketones or aldehydes: An efficient route for the synthesis of 1,2-amino alcohols

The cross-coupling reactions of imines with ketones using Ti(O iPr)4/c-C5H9MgCl reagent lead to 1,2-amino alcohols after hydrolysis. The coupling reactions with aldehydes could also afford 1,2-amino alcohols, however, in some cases, aziridines were obtained as major products in a stereoselective manner.

Origins of stereoselectivity in optically pure phenylethaniminopyridine tris-chelates M(NN′)3n+ (M = Mn, Fe, Co, Ni and Zn)

One-pot reactions of 2-pyridinecarboxaldehyde, chiral phenylethanamines and Fe(ii) give single diastereomer fac diimine complexes at thermodynamic equilibrium so that no chiral separations are required (d.r. > 200:1). The origins of this stereoselectivity are partly steric and partly a result of the presence of three sets of inter-ligand parallel-offset π-stacking interactions. Mn(ii), Co(ii), Co(iii), Ni(ii) and Zn(ii) give similar fac structures, alongside the imidazole analogues for Fe(ii). While most of the complexes are paramagnetic, the series of molecular structures allows us to assess the influence of the π-stacking present, and there is a strong correlation between this and the M-N bond length. Fe(ii) is close to optimal. For the larger Zn(ii) ion, very weak π-stacking leads to poorer measured stereoselectivity (NMR) but this is improved with increased solvent polarity. The mechanism of stereoselection is further investigated via DFT calculations, chiroptical spectroscopy and the use of synthetic probes.

A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation

The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.

Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction

The chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams was investigated from ethylbromodifluoroacetate and imines during Reformatsky reaction. Influence of various reaction parameters, such as nature of the amine part, nature of the chiral auxiliary, was evaluated. High levels of stereoselectivity (up to 98%) were obtained for gem-difluoro-β-aminoesters and gem-difluoro-β-lactams using either (R)-phenylglycinol or (R)-methoxyphenylglycinol.

Functionalized pyrrolidines inhibit α-mannosidase activity and growth of human glioblastoma and melanoma cells

New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases we

THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).