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  • Title: N(2)-Aroylanthranilamide inhibitors of human factor Xa.
    Author: Yee YK, Tebbe AL, Linebarger JH, Beight DW, Craft TJ, Gifford-Moore D, Goodson T, Herron DK, Klimkowski VJ, Kyle JA, Sawyer JS, Smith GF, Tinsley JM, Towner RD, Weir L, Wiley MR.
    Journal: J Med Chem; 2000 Mar 09; 43(5):873-82. PubMed ID: 10715154.
    Abstract:
    Reversal of the A-ring amide link in 1,2-dibenzamidobenzene 1 (fXa K(ass) = 0.81 x 10(6) L/mol) led to a series of human factor Xa (hfXa) inhibitors based on N(2)-aroylanthranilamide 4. Expansion of the SAR around 4 showed that only small planar substituents could be accommodated in the A-ring for binding to the S1 site of hfXa. Bulky groups such as 4-isopropyl, 4-tert-butyl, and 4-dimethylamino were favored in the B-ring to interact with the S4 site of hfXa. The central (C) ring containing a 5-methanesulfonamido group yielded greater activity than carbamoyl groups. Combining the beneficial features from the B- and C-ring SAR, compound 55 represents the most potent hfXa inhibitor in the N(2)-aroylanthranilamide 4 series with hfXa K(ass) = 58 x 10(6) L/mol (K(i) = 11.5 nM).
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