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Design, synthesis and biological activity of novel rigid amidino-phenylalanine derivatives as inhibitors of thrombin. 1995

H Mack, and T Pfeiffer, and W Hornberger, and H J Böhm, and H W Höffken
Main Laboratory, Pharmaceuticals Research, Ludwigshafen, Germany.

(3S)-(Naphthalene-2-sulfonylamino)-1-[2R-(4-amidinophenyl)-1- piperidinocarbonylethyl]-2-pyrrolidinone (1a) is a potent inhibitor of thrombin with an IC50 value by 112 times lower than that of NAPAP (racemate). The selectivity versus trypsin can be improved by incorporation of substituents on the naphthyl ring. The mode of binding of the compound was determined by X-ray crystallography.

UI MeSH Term Description Entries
D007769 Lactams Cyclic AMIDES formed from aminocarboxylic acids by the elimination of water. Lactims are the enol forms of lactams. Lactam,Lactim,Lactims
D010880 Piperidines A family of hexahydropyridines.
D011760 Pyrrolidinones A group of compounds that are derivatives of oxo-pyrrolidines. A member of this group is 2-oxo pyrrolidine, which is an intermediate in the manufacture of polyvinylpyrrolidone. (From Merck Index, 11th ed) Pyrrolidinone,Pyrrolidone,Pyrrolidones
D004151 Dipeptides Peptides composed of two amino acid units. Dipeptide
D006860 Hydrogen Bonding A low-energy attractive force between hydrogen and another element. It plays a major role in determining the properties of water, proteins, and other compounds. Hydrogen Bonds,Bond, Hydrogen,Hydrogen Bond
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000991 Antithrombins Endogenous factors and drugs that directly inhibit the action of THROMBIN, usually by blocking its enzymatic activity. They are distinguished from INDIRECT THROMBIN INHIBITORS, such as HEPARIN, which act by enhancing the inhibitory effects of antithrombins. Antithrombin,Direct Antithrombin,Direct Antithrombins,Direct Thrombin Inhibitor,Direct Thrombin Inhibitors,Antithrombin, Direct,Antithrombins, Direct,Inhibitor, Direct Thrombin,Thrombin Inhibitor, Direct,Thrombin Inhibitors, Direct
D001550 Benzamidines Amidines substituted with a benzene group. Benzamidine and its derivatives are known as peptidase inhibitors.
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D001667 Binding, Competitive The interaction of two or more substrates or ligands with the same binding site. The displacement of one by the other is used in quantitative and selective affinity measurements. Competitive Binding

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