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Chem Pharm Bull (Tokyo) ; 57(9): 1004-7, 2009 Sep.
Article in English | MEDLINE | ID: mdl-19721266

ABSTRACT

Based upon the biphenyl 1-(2-naphthyl)-1H-pyrazole-5-carboxylamides reported in our previous communications, we designed and discovered 2-(6-chloro-3-methylsulfonyl)-naphthyl as an optimal factor Xa S1 binding element. Employing a key Diels-Alder reaction of 1,4-dihydro-2,3-benzoxathiin-3-oxide with maleic anhydride and a key Cu(I)-mediated methylsulfonylation, we prepared two biphenyl 1-(2-(6-chloro-3-methylsulfonyl)-naphthyl)-1H-pyrazole-5-carboxylamides as highly potent factor Xa inhibitors with K(i) values of 0.065 nM and 0.045 nM respectively, and demonstrated the synergistically enhanced binding interaction in the factor Xa S1 site.


Subject(s)
Amides/chemical synthesis , Factor Xa Inhibitors , Serine Proteinase Inhibitors/chemical synthesis , Amides/chemistry , Amides/pharmacology , Binding Sites , Drug Design , Factor Xa/metabolism , Protein Binding , Serine Proteinase Inhibitors/chemistry , Serine Proteinase Inhibitors/pharmacology
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