340188-50-3

Usage

Chemical Properties

white powder

InChI:InChI=1/C11H15NO2/c1-2-14-11(13)8-10(12)9-6-4-3-5-7-9/h3-7,10H,2,8,12H2,1H3/p+1/t10-/m1/s1

Upstream product

• 64-17-5 ethanol 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 471259-71-9 (RS)-3-amino-3-phenyl-propionic acid hydrochloride 
• 864871-38-5 diethyl 2-(1-(N-tert-butoxycarbonylamino)-1-phenylmethyl)malonate 
• 100-52-7 benzaldehyde 
• 402828-05-1 (R)-1-butyryloxymethyl-4-phenyl-2-azetidinone 
• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 167834-23-3 ethyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoate 
• 1245606-49-8 (Z)-3-ethoxy-3-oxo-1-phenylprop-1-en-1-amine hydrochloride 
• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 371-27-7 2,2,2-trifluoroethylbutyrate 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 

Downstream Products

• 1021464-42-5 ethyl 3-phenyl-3-(trimethylsiloxycarbonylamino)propanoate 
• 232594-62-6 ethyl rac-3-(2-benzyloxycarbonylamino-acetylamino)-3-phenyl-propionate 
• 100049-94-3 ethyl 3-amino-3-cyclohexylpropanoate hydrochloride 
• 376348-65-1 maraviroc 
• 376348-77-5 (S)-4,4-difluoro-N-(3-hydroxy-1-phenylpropyl)cyclohexanecarboxamide 
• 376348-78-6 4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide 
• 376348-76-4 ethyl (S)-3-[(4,4-difluorocyclohexyl)carboxamido]-3-phenylpropanoate 
• 872001-84-8 C₁₇H₂₄N₂O₃ 
• 872001-83-7 C₁₅H₁₉NO₃ 
• 872001-85-9 cyclopentanecarboxylic acid (3-oxo-1-phenyl-butyl)-amide 

Relevant academic research and scientific papers

Turn Conformation of β-Amino Acid-Based Short Peptides Promoted by an Amidothiourea Moiety at C-Terminus

A C-terminal amidothiourea motif is shown to promote a β-turn-like folded conformation in a series of β-amino acid-based short peptides in both the solid state and solution phase by an intramolecular 11-membered ring hydrogen bond.

Structure activity relationships of αv integrin antagonists for pulmonary fibrosis by variation in aryl substituents

Antagonism of αvβ6 is emerging as a potential treatment of idiopathic pulmonary fibrosis based on strong target validation. Starting from an αvβ3 antagonist lead and through simple variation in the nature and position of the aryl substituent, the discovery of compounds with improved αvβ6 activity is described. The compounds also have physicochemical properties commensurate with oral bioavailability and are high quality starting points for a drug discovery program. Compounds 33S and 43E1 are pan αv antagonists having ca. 100 nM potency against αvβ3, αvβ5, αvβ6, and αvβ8 in cell adhesion assays. Detailed structure activity relationships with these integrins are described which also reveal substituents providing partial selectivity (defined as at least a 0.7 log difference in pIC50 values between the integrins in question) for αvβ3 and αvβ5.

USE OF CONDENSED BENZO[B]THIAZINE DERIVATIVES AS CYTOPROTECTANTS

The present invention relates to arylthiazine compounds, metabolites, N-oxides, amides, esters,pharmaceutically acceptable salts, hydrates and solvates thereof and their use as cytoprotectants in the treatment or prophylaxis of diseases or states, either acute or chronic, involving aberrant cellular lipid peroxidation in the central nervous system or in the periphery of the body. The present invention also relates to a method for their preparation and to pharmaceutical composition comprising as an active ingredient one or more of the aforementioned compounds.

Highly efficient iridium-catalyzed asymmetric hydrogenation of unprotected β-enamine esters

A highly efficient and enantioselective hydrogenation of unprotected β-enamine esters catalyzed by Ir-(S,S)-f-Binaphane complex has been developed. This methodology provides straightforward access to free β-amino acids in high yields with excellent enantioselectivities up to 97% ee and high reactivities (TON > 5000).

An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers

An efficient synthesis of β-aryl-β-amino acid enantiomers has been developed via the lipase-catalysed enantioselective hydrolysis of the corresponding racemic ethyl esters in an organic solvent. High enantioselectivities (E >100) were observed when the lipase PS-catalysed reactions were performed with H2O (0.5 equiv) in diisopropyl ether at 45 °C. The products could be easily separated and were obtained in good yields of ≥40%.

Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters

Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, β-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The 1H NMR spectra show that monosilyl urethanes derived from α-and β-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group. Nauka/Interperiodica 2007.

Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is required after phosgeneation. Unusual generation of cynnamates and intramolecular N→O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic β-aminoacid esters were found. Pleiades Publishing, Inc., 2006.

New access to racemic β3-amino acids

A general simple procedure having the potential for large scale preparations of racemic β3-amino acids has been developed. The procedure involves base-catalyzed Michael-type addition of sodium diethyl malonate to N-Boc-α-amidoalkyl-p-tolyl sulfones in tetrahydrofuran. Hydrolysis of the adducts by refluxing with 6 M aqueous hydrochloric acid affords β3-amino acid hydrochlorides in high yield and excellent purity.

Spiroimidazolidine derivatives, their preparation, their use and pharmaceutical preparations formed therefrom

The present invention relates to spiroimidazolidine derivatives of the formula I in which E, V, W, X, R1and R2have the meanings indicated in the claims. The compounds of the formula I are valuable pharmaceutical active compounds which are suitable, for example, for the therapy and prophylaxis of inflammatory disorders, such as, for example, rheumatoid arthritis, or allergic disorders. The compounds of the formula I are also inhibitors of the adhesion and migration of leukocytes and/or antagonists of the adhesion receptor VLA-4 belonging to the integrins group. They are generally suitable for the therapy and prophylaxis of illnesses which are caused by an undesired extent of leukocyte adhesion and/or leukocyte migration or are associated therewith or in which cell-cell or cell-matrix interactions which are based on interactions of VLA-4 receptors with their ligands play a part. The invention also relates to processes for the preparation of the compounds of the formula I, pharmaceutical preparations which contain compounds of the formula I, and methods for treating these disorders.