797040-06-3

Upstream product

• 108-24-7 acetic anhydride 
• 797040-05-2 3-[3-(N-hydroxycarbamimidoyl)-phenyl]-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propionic acid 
• 797040-05-2 Tips-Phe(3-OAm)-OH 
• 57213-48-6 3-cyano-(D,L)-phenylalanine 
• 6553-96-4 2,4,6-triisopropylphenylsulfonyl chloride 
• 255374-80-2 Nα-2,4,6-Triisopropylphenylsulfonyl-(L)-3-cyano-phenylalanine 

Downstream Products

• 300579-37-7 3-[(S)-3-[4-(3-Amino-propionyl)-piperazin-1-yl]-3-oxo-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propyl]-benzamidine 
• 797040-25-6 3-[(S)-3-[4-(4-Amino-butyryl)-piperazin-1-yl]-3-oxo-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propyl]-benzamidine 
• 797040-12-1 1-[(S)-3-(3-Carbamimidoyl-phenyl)-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propionyl]-piperidine-4-carboxylic acid (2-amino-ethyl)-amide 
• 901771-96-8 3-[(S)-3-[4-(3-Amino-propionyl)-[1,4]diazepan-1-yl]-3-oxo-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propyl]-benzamidine 
• 797040-69-8 3-[(S)-3-Oxo-3-[4-(piperazine-1-carbonyl)-piperidin-1-yl]-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propyl]-benzamidine 
• 797040-45-0 3-[(S)-3-Oxo-3-[4-(piperidine-4-carbonyl)-piperazin-1-yl]-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propyl]-benzamidine 

Relevant academic research and scientific papers

Secondary amides of sulfonylated 3-amidinophenylalanine. New potent and selective inhibitors of matriptase

Matriptase is an epithelium-derived type II transmembrane serine protease and has been implicated in the activation of substrates such as pro-HGF/SF and pro-uPA, which are likely involved in tumor progression and metastasis. Through screening, we have identified bis-basic secondary amides of sulfonylated 3-amidinophenylalanine as matriptase inhibitors. X-ray analyses of analogues 8 and 31 in complex with matriptase revealed that these inhibitors occupy, in addition to part of the previously described S4-binding site, the cleft formed by the molecular surface and the unique 60 loop of matriptase. Therefore, optimization of the inhibitors included the incorporation of appropriate sulfonyl substituents that could improve binding of these inhibitors into both characteristic matriptase subsites. The most potent derivatives inhibit matriptase highly selective with Ki values below 5 nM. Molecular modeling revealed that their improved affinity results from interaction with the S4 site of matriptase. Analogues 8 and 59 were studied in an orthotopic xenograft mouse model of prostate cancer. Compared to control, both inhibitors reduced tumor growth, as well as tumor dissemination.

N-SULPHONYLATED AMINO ACID DERIVATIVES, METHOD FOR THE PRODUCTION AND USE THEREOF

The invention relates to N-sulphonylated amino acid derivatives wherein an aryl radical is bound to an amino acid via the sulphonyl groups in the N-terminal and a radical is bound in the C-terminal via the carbonyl group. Said radical contains at least one imino group and at least one other basic group representing an optionally modified amino-, amidino- or guanidino group. The invention also relates to a method for the production of said compounds and to the use thereof, especially as inhibitors of matriptase.

3-Amidinophenylalanine-based inhibitors of urokinase

Synthesis and anti-uPA activity of a series of Nα-triisopropyl-phenylsulfonyl-protected 3-amidino-phenylalanine amides are described. We have explored SAR around the C-terminal amide part for inhibition of uPA, plasmin and trypsin. Modification of the ami