255375-04-3Relevant academic research and scientific papers
METHOD FOR THE PRODUCTION OF PHENYLALANINE DERIVATIVES
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Page/Page column 8, (2008/06/13)
The invention relates to an improved method for the production of 3-amidino- or 3-guanidinophenylalanine derivatives, especially triisopropylphenyl-sulfonyl-substituted 3-amidino- or 3-guanidinophenylalanine derivatives.
3-Amidinophenylalanine-based inhibitors of urokinase
Stuerzebecher, Joerg,Vieweg, Helmut,Steinmetzer, Torsten,Schweinitz, Andrea,Stubbs, Milton T.,Renatus, Martin,Wikstroem, Peter
, p. 3147 - 3152 (2007/10/03)
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
Synthesis and structure-activity relationships of potent thrombin inhibitors: Piperazides of 3-amidinophenylalanine
Stürzebecher, J?rg,Prasa, Dagmar,Hauptmann, J?rg,Vieweg, Helmut,Wikstr?m, Peter
, p. 3091 - 3099 (2007/10/03)
Thrombin is the key enzyme in the blood coagulation system, and inhibitors of its proteolytic activity are of therapeutic interest since they are potential anticoagulants. The most potent inhibitor of the benzamidine type is N(α)-[(2-naphthylsulfonyl)glycyl]-4-amidinophenylalanylpiperidide (NAPAP). However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration. The goal of designing new compounds was to obtain potent inhibitors with improved pharmacokinetic properties. Piperazide derivatives of 3-amidinophenylalanine as the key building block were synthesized. The piperazine moiety opened the possibility to introduce quite different substituents on the second nitrogen using common synthetic procedures. Some of the newly synthesized compounds are potent inhibitors of thrombin and offer an approach to study structure-function relationships for inhibition of thrombin and related enzymes and for the improvement of their pharmacokinetic properties.
