29754-04-9

Upstream product

• 64-17-5 ethanol 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 100-52-7 benzaldehyde 
• 864871-38-5 diethyl 2-(1-(N-tert-butoxycarbonylamino)-1-phenylmethyl)malonate 
• 471259-71-9 (RS)-3-amino-3-phenyl-propionic acid hydrochloride 
• 271600-36-3 N-[phenyl(toluene-4-sulfonyl)methyl]tert-butoxycarboxyamide 

Downstream Products

• 88636-83-3 ethyl 3-phenyl-3-isocyanatopropanoate 
• 210161-76-5 ethyl-3-[3N'-(2-chloroethyl)ureido]-3-phenylpropionate 
• 26674-16-8 6-methyl-2-phenyl-2,3-dihydropyridin-4(1H)-one 
• 498581-99-0 2-methyl-4-oxo-6-phenyl-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid tert-butyl ester 
• 232594-62-6 ethyl rac-3-(2-benzyloxycarbonylamino-acetylamino)-3-phenyl-propionate 
• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 3082-68-6 (R)-3-amino-3-phenylpropionic acid ethyl ester 
• 697764-20-8 ethyl 3-(3,4-dimethoxybenzylideneamino)-3-phenylpropanoate 
• 697763-51-2 ethyl 3-benzylideneamino-3-phenylpropanoate 
• 262278-79-5 (+/-)-3-[(8-Chloro-4-oxo-4H-quinolizine-3-carbonyl)-amino]-3-phenyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

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.

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.

A versatile and efficient synthesis of 2-alkyl and 2-aryl-6-alkyl-2,3-dihydro-1H-pyridin-4-ones

A versatile and efficient method for the preparation of 2-alkyl and 2-aryl-6-alkyl-2,3-dihydro-1H-pyridin-4-ones is described. The sequence involved the condensation of β-amino acids and t-butyl ketoester to give enaminoesters whose intramolecular cyclisation followed by an hydrolysis step afforded the expected products.

Bispiperidines as antithrombotic agents

Novel compounds which are inhibitors of the binding of fibrinogen to the Gp IIb/IIIa platelet receptors, and which can be used therepeutically as antithrombotic agents

N-(diethoxyphosphoryl)aldimines as synthetic equivalents of A1 type synthons

Novel organophosphorus reagents useful for convergent synthesis of primary amines are presented.