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Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 20, 2004, Pages 5165-5170

Design, synthesis, and evaluation of oxyanion-hole selective inhibitor substituents for the S1 subsite of factor Xa

(8) Rumthao, Sochanchingwung a Lee, Oukseub a Sheng, Qi a Fu, Wentao a Mulhearn, Debbie C a Crich, David a Mesecar, Andrew D a Johnson, Michael E a

a UNIVERSITY OF ILLINOIS AT CHICAGO (United States)

Author keywords

Factor Xa; Oxyanion hole; p Hydroxybenzamidine; S1 specificity pocket; Serine protease inhibitor

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; BLOOD CLOTTING FACTOR 10A INHIBITOR; SULFONE DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CATALYSIS; DRUG ACTIVITY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; HYDROGEN BOND; IONIZATION;

ALCOHOLS; AMINES; ANIONS; BENZAMIDINES; CATALYTIC DOMAIN; FACTOR XA; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES;

EID: 4544272635 PISSN: 0960894X EISSN: None Source Type: Journal
DOI: 10.1016/j.bmcl.2004.07.054 Document Type: Article

Times cited : (6)

References (41)

1
- 77956750628
- J.M. Fevig, and R.R. Wexler Annu. Rep. Med. Chem. 34 1999 81
- (1999) Annu. Rep. Med. Chem. , vol.34 , pp. 81
- Fevig, J.M.¹ Wexler, R.R.²

2
- 0029868652
- F.A. Nicolini, P. Lee, J.L. Malycky, J. Lefkovits, K. Kottke-Marchant, E.F. Plow, and E.J. Topol Blood Coagul. Fibrin. 7 1996 39
- (1996) Blood Coagul. Fibrin. , vol.7 , pp. 39
- Nicolini, F.A.¹ Lee, P.² Malycky, J.L.³ Lefkovits, J.⁴ Kottke-Marchant, K.⁵ Plow, E.F.⁶ Topol, E.J.⁷

3
- 0035004409
- R. Rai, P.A. Sprengeler, K.C. Elrod, and W.B. Young Curr. Med. Chem. 8 2001 101
- (2001) Curr. Med. Chem. , vol.8 , pp. 101
- Rai, R.¹ Sprengeler, P.A.² Elrod, K.C.³ Young, W.B.⁴

4
- 0033859659
- J.P. Vacca Curr. Opin. Chem. Biol. 4 2000 394
- (2000) Curr. Opin. Chem. Biol. , vol.4 , pp. 394
- Vacca, J.P.¹

5
- 0035383551
- B.Y. Zhu, W. Huang, T. Su, C. Marlowe, U. Sinha, S. Hollenbach, and R.M. Scarborough Curr. Top. Med. Chem. (Hilversum, Neth.) 1 2001 101
- (2001) Curr. Top. Med. Chem. (Hilversum, Neth.) , vol.1 , pp. 101
- Zhu, B.Y.¹ Huang, W.² Su, T.³ Marlowe, C.⁴ Sinha, U.⁵ Hollenbach, S.⁶ Scarborough, R.M.⁷

6
- 3042749886
- B.Y. Zhu, and R.M. Scarborough Annu. Rep. Med. Chem. 35 2000 83
- (2000) Annu. Rep. Med. Chem. , vol.35 , pp. 83
- Zhu, B.Y.¹ Scarborough, R.M.²

7
- 0033167327
- Y. Zhou, and M.E. Johnson J. Mol. Recognit. 12 1999 235
- (1999) J. Mol. Recognit. , vol.12 , pp. 235
- Zhou, Y.¹ Johnson, M.E.²

8
- 0036132023
- J. Cui, F. Marankan, W. Fu, D. Crich, A. Mesecar, and M.E. Johnson Bioorg. Med. Chem. 10 2002 41
- (2002) Bioorg. Med. Chem. , vol.10 , pp. 41
- Cui, J.¹ Marankan, F.² Fu, W.³ Crich, D.⁴ Mesecar, A.⁵ Johnson, M.E.⁶

9
- 0034680369
- M. Adler, D.D. Davey, G.B. Phillips, S.H. Kim, J. Jancarik, G. Rumennik, D.R. Light, and M. Whitlow Biochemistry 39 2000 12534
- (2000) Biochemistry , vol.39 , pp. 12534
- Adler, M.¹ Davey, D.D.² Phillips, G.B.³ Kim, S.H.⁴ Jancarik, J.⁵ Rumennik, G.⁶ Light, D.R.⁷ Whitlow, M.⁸

10
- 0033947739
- V. Chu, K. Brown, D. Colussi, Y.M. Choi, D. Green, H.W. Pauls, A.P. Spada, M.H. Perrone, R.J. Leadley Jr., and C.T. Dunwiddie Thromb. Res. 99 2000 71
- (2000) Thromb. Res. , vol.99 , pp. 71
- Chu, V.¹ Brown, K.² Colussi, D.³ Choi, Y.M.⁴ Green, D.⁵ Pauls, H.W.⁶ Spada, A.P.⁷ Perrone, M.H.⁸ Leadley Jr., R.J.⁹ Dunwiddie, C.T.¹⁰

11
- 0034614995
- Y. Gong, H.W. Pauls, A.P. Spada, M. Czekaj, G. Liang, V. Chu, D.J. Colussi, K.D. Brown, and J. Gao Bioorg. Med. Chem. Lett. 10 2000 217
- (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 217
- Gong, Y.¹ Pauls, H.W.² Spada, A.P.³ Czekaj, M.⁴ Liang, G.⁵ Chu, V.⁶ Colussi, D.J.⁷ Brown, K.D.⁸ Gao, J.⁹

12
- 0034710722
- S. Maignan, J.P. Guilloteau, S. Pouzieux, Y.M. Choi-Sledeski, M.R. Becker, S.I. Klein, W.R. Ewing, H.W. Pauls, A.P. Spada, and V. Mikol J. Med. Chem. 43 2000 3226
- (2000) J. Med. Chem. , vol.43 , pp. 3226
- Maignan, S.¹ Guilloteau, J.P.² Pouzieux, S.³ Choi-Sledeski, Y.M.⁴ Becker, M.R.⁵ Klein, S.I.⁶ Ewing, W.R.⁷ Pauls, H.W.⁸ Spada, A.P.⁹ Mikol, V.¹⁰

13
- 0035383371
- H.W. Pauls, and W.R. Ewing Curr. Top. Med. Chem. 1 2001 83
- (2001) Curr. Top. Med. Chem. , vol.1 , pp. 83
- Pauls, H.W.¹ Ewing, W.R.²

14
- 0037030682
- G. Phillips, W.J. Guilford, B.O. Buckman, D.D. Davey, K.A. Eagen, S. Koovakkat, A. Liang, M. McCarrick, R. Mohan, H.P. Ng, M. Pinkerton, B. Subramanyam, E. Ho, L. Trinh, M. Whitlow, S. Wu, W. Xu, and M.M. Morrissey J. Med. Chem. 45 2002 2484
- (2002) J. Med. Chem. , vol.45 , pp. 2484
- Phillips, G.¹ Guilford, W.J.² Buckman, B.O.³ Davey, D.D.⁴ Eagen, K.A.⁵ Koovakkat, S.⁶ Liang, A.⁷ McCarrick, M.⁸ Mohan, R.⁹ Ng, H.P.¹⁰ Pinkerton, M.¹¹ Subramanyam, B.¹² Ho, E.¹³ Trinh, L.¹⁴ Whitlow, M.¹⁵ Wu, S.¹⁶ Xu, W.¹⁷ Morrissey, M.M.¹⁸

15
- 0037124198
- Z.J. Jia, Y. Wu, W. Huang, E. Goldman, P. Zhang, J. Woolfrey, P. Wong, B. Huang, U. Sinha, G. Park, A. Reed, R.M. Scarborough, and B.Y. Zhu Bioorg. Med. Chem. Lett. 12 2002 1651
- (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1651
- Jia, Z.J.¹ Wu, Y.² Huang, W.³ Goldman, E.⁴ Zhang, P.⁵ Woolfrey, J.⁶ Wong, P.⁷ Huang, B.⁸ Sinha, U.⁹ Park, G.¹⁰ Reed, A.¹¹ Scarborough, R.M.¹² Zhu, B.Y.¹³

16
- 4544383444
- PCT Int. Appl. (Ajinomoto Co., Inc., Japan) WO, 1999;
- Nakagawa, T.; Sagi, K.; Yoshida, K.; Fukuda, Y.; Shoji, M.; Takehana, S.; Kayahara, T.; Takahara, A. PCT Int. Appl. (Ajinomoto Co., Inc., Japan) WO, 1999; p 143
- Nakagawa, T.¹ Sagi, K.² Yoshida, K.³ Fukuda, Y.⁴ Shoji, M.⁵ Takehana, S.⁶ Kayahara, T.⁷ Takahara, A.⁸

17
- 0032561224
- B. Gabriel, M.T. Stubbs, A. Bergner, J. Hauptmann, W. Bode, J. Sturzebecher, and L. Moroder J. Med. Chem. 41 1998 4240
- (1998) J. Med. Chem. , vol.41 , pp. 4240
- Gabriel, B.¹ Stubbs, M.T.² Bergner, A.³ Hauptmann, J.⁴ Bode, W.⁵ Sturzebecher, J.⁶ Moroder, L.⁷

18
- 0035151738
- H. Nar, M. Bauer, A. Schmid, J.M. Stassen, W. Wienen, H.W. Priepke, I.K. Kauffmann, U.J. Ries, and N.H. Hauel Structure (Camb.) 9 2001 29
- (2001) Structure (Camb.) , vol.9 , pp. 29
- Nar, H.¹ Bauer, M.² Schmid, A.³ Stassen, J.M.⁴ Wienen, W.⁵ Priepke, H.W.⁶ Kauffmann, I.K.⁷ Ries, U.J.⁸ Hauel, N.H.⁹

19
- 0032499683
- K. Kamata, H. Kawamoto, T. Honma, T. Iwama, and S.H. Kim Proc. Natl. Acad. Sci. U.S.A. 95 1998 6630
- (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 6630
- Kamata, K.¹ Kawamoto, H.² Honma, T.³ Iwama, T.⁴ Kim, S.H.⁵

20
- 0037124202
- K.R. Guertin, C.J. Gardner, S.I. Klein, A.L. Zulli, M. Czekaj, Y. Gong, A.P. Spada, D.L. Cheney, S. Maignan, J.P. Guilloteau, K.D. Brown, D.J. Colussi, V. Chu, C.L. Heran, S.R. Morgan, R.G. Bentley, C.T. Dunwiddie, R.J. Leadley, and H.W. Pauls Bioorg. Med. Chem. Lett. 12 2002 1671
- (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1671
- Guertin, K.R.¹ Gardner, C.J.² Klein, S.I.³ Zulli, A.L.⁴ Czekaj, M.⁵ Gong, Y.⁶ Spada, A.P.⁷ Cheney, D.L.⁸ Maignan, S.⁹ Guilloteau, J.P.¹⁰ Brown, K.D.¹¹ Colussi, D.J.¹² Chu, V.¹³ Heran, C.L.¹⁴ Morgan, S.R.¹⁵ Bentley, R.G.¹⁶ Dunwiddie, C.T.¹⁷ Leadley, R.J.¹⁸ Pauls, H.W.¹⁹

21
- 0036661082
- M.M. Mueller, S. Sperl, J. Sturzebecher, W. Bode, and L. Moroder Biol. Chem. 383 2002 1185
- (2002) Biol. Chem. , vol.383 , pp. 1185
- Mueller, M.M.¹ Sperl, S.² Sturzebecher, J.³ Bode, W.⁴ Moroder, L.⁵

22
- 0037142372
- H. Matter, E. Defossa, U. Heinelt, P.M. Blohm, D. Schneider, A. Muller, S. Herok, H. Schreuder, A. Liesum, V. Brachvogel, P. Lonze, A. Walser, F. Al-Obeidi, and P. Wildgoose J. Med. Chem. 45 2002 2749
- (2002) J. Med. Chem. , vol.45 , pp. 2749
- Matter, H.¹ Defossa, E.² Heinelt, U.³ Blohm, P.M.⁴ Schneider, D.⁵ Muller, A.⁶ Herok, S.⁷ Schreuder, H.⁸ Liesum, A.⁹ Brachvogel, V.¹⁰ Lonze, P.¹¹ Walser, A.¹² Al-Obeidi, F.¹³ Wildgoose, P.¹⁴

23
- 0037124195
- P. Zhang, J.F. Zuckett, J. Woolfrey, K. Tran, B. Huang, P. Wong, U. Sinha, G. Park, A. Reed, J. Malinowski, S. Hollenbach, R.M. Scarborough, and B.Y. Zhu Bioorg. Med. Chem. Lett. 12 2002 1657
- (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1657
- Zhang, P.¹ Zuckett, J.F.² Woolfrey, J.³ Tran, K.⁴ Huang, B.⁵ Wong, P.⁶ Sinha, U.⁷ Park, G.⁸ Reed, A.⁹ Malinowski, J.¹⁰ Hollenbach, S.¹¹ Scarborough, R.M.¹² Zhu, B.Y.¹³

24
- 0033535401
- J.B. Rewinkel, H. Lucas, P.J. van Galen, A.B. Noach, T.G. van Dinther, A.M. Rood, A.J. Jenneboer, and C.A. van Boeckel Bioorg. Med. Chem. Lett. 9 1999 685
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 685
- Rewinkel, J.B.¹ Lucas, H.² Van Galen, P.J.³ Noach, A.B.⁴ Van Dinther, T.G.⁵ Rood, A.M.⁶ Jenneboer, A.J.⁷ Van Boeckel, C.A.⁸

25
- 0034624694
- Y.K. Yee, A.L. Tebbe, J.H. Linebarger, D.W. Beight, T.J. Craft, D. Gifford-Moore, T. Goodson Jr., D.K. Herron, V.J. Klimkowski, J.A. Kyle, J.S. Sawyer, G.F. Smith, J.M. Tinsley, R.D. Towner, L. Weir, and M.R. Wiley J. Med. Chem. 43 2000 873
- (2000) J. Med. Chem. , vol.43 , pp. 873
- Yee, Y.K.¹ Tebbe, A.L.² Linebarger, J.H.³ Beight, D.W.⁴ Craft, T.J.⁵ Gifford-Moore, D.⁶ Goodson Jr., T.⁷ Herron, D.K.⁸ Klimkowski, V.J.⁹ Kyle, J.A.¹⁰ Sawyer, J.S.¹¹ Smith, G.F.¹² Tinsley, J.M.¹³ Towner, R.D.¹⁴ Weir, L.¹⁵ Wiley, M.R.¹⁶

26
- 17444438416
- D.K. Herron, T. Goodson Jr., M.R. Wiley, L.C. Weir, J.A. Kyle, Y.K. Yee, A.L. Tebbe, J.M. Tinsley, D. Mendel, J.J. Masters, J.B. Franciskovich, J.S. Sawyer, D.W. Beight, A.M. Ratz, G. Milot, S.E. Hall, V.J. Klimkowski, J.H. Wikel, B.J. Eastwood, R.D. Towner, D.S. Gifford-Moore, T.J. Craft, and G.F. Smith J. Med. Chem. 43 2000 859
- (2000) J. Med. Chem. , vol.43 , pp. 859
- Herron, D.K.¹ Goodson Jr., T.² Wiley, M.R.³ Weir, L.C.⁴ Kyle, J.A.⁵ Yee, Y.K.⁶ Tebbe, A.L.⁷ Tinsley, J.M.⁸ Mendel, D.⁹ Masters, J.J.¹⁰ Franciskovich, J.B.¹¹ Sawyer, J.S.¹² Beight, D.W.¹³ Ratz, A.M.¹⁴ Milot, G.¹⁵ Hall, S.E.¹⁶ Klimkowski, V.J.¹⁷ Wikel, J.H.¹⁸ Eastwood, B.J.¹⁹ Towner, R.D.²⁰ more..

27
- 37049176154
- H.S. Forrest, A.T. Fuller, and J. Walker J. Chem. Soc. 1948 1501
- (1948) J. Chem. Soc. , pp. 1501
- Forrest, H.S.¹ Fuller, A.T.² Walker, J.³

28
- 37049161963
- A.T. Fuller, I.M. Tonkin, and J. Walker J. Chem. Soc. 1945 633
- (1945) J. Chem. Soc. , pp. 633
- Fuller, A.T.¹ Tonkin, I.M.² Walker, J.³

29
- 0001782430
- E. Crundwell J. Chem. Soc. 1956 368
- (1956) J. Chem. Soc. , pp. 368
- Crundwell, E.¹

30
- 84955774900
- A. Pinner, and F. Gradenwitz Liebigs Ann. Chem. 298 1897 47
- (1897) Liebigs Ann. Chem. , vol.298 , pp. 47
- Pinner, A.¹ Gradenwitz, F.²

31
- 37049175414
- M.W. Partridge, and W.F. Short J. Chem. Soc. 1947 390
- (1947) J. Chem. Soc. , pp. 390
- Partridge, M.W.¹ Short, W.F.²

32
- 0021679875
- T. Yaegashi, S. Nunomura, T. Okutome, T. Nakayama, M. Kurumi, Y. Sakurai, T. Aoyama, and S. Fujii Chem. Pharm. Bull. 32 1984 4466
- (1984) Chem. Pharm. Bull. , vol.32 , pp. 4466
- Yaegashi, T.¹ Nunomura, S.² Okutome, T.³ Nakayama, T.⁴ Kurumi, M.⁵ Sakurai, Y.⁶ Aoyama, T.⁷ Fujii, S.⁸

33
- 4544236930
- G. Wagner, and H. Vieweg Pharmazie 37 1982 13
- (1982) Pharmazie , vol.37 , pp. 13
- Wagner, G.¹ Vieweg, H.²

34
- 0031794772
- C. Lila, P. Gloanec, L. Cadet, Y. Herve, J. Fournier, F. Leborgne, T.J. Verbeuren, and G. De Nanteuil Synth. Commun. 28 1998 4419
- (1998) Synth. Commun. , vol.28 , pp. 4419
- Lila, C.¹ Gloanec, P.² Cadet, L.³ Herve, Y.⁴ Fournier, J.⁵ Leborgne, F.⁶ Verbeuren, T.J.⁷ De Nanteuil, G.⁸

35
- 0028076366
- J.L. Acena, O. Arjona, R. Fernandez de la Pradilla, J. Plumet, and A. Viso J. Org. Chem. 59 1994 6419
- (1994) J. Org. Chem. , vol.59 , pp. 6419
- Acena, J.L.¹ Arjona, O.² Fernandez De La Pradilla, R.³ Plumet, J.⁴ Viso, A.⁵

36
- 0030598188
- M.R. Wiley, N.Y. Chirgadze, D.K. Clawson, T.J. Craft, D.S. Gifford-Moore, N.D. Jones, J.L. Olkowski, L.C. Weir, and G.F. Smith Bioorg. Med. Chem. Lett. 6 1996 2387
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2387
- Wiley, M.R.¹ Chirgadze, N.Y.² Clawson, D.K.³ Craft, T.J.⁴ Gifford-Moore, D.S.⁵ Jones, N.D.⁶ Olkowski, J.L.⁷ Weir, L.C.⁸ Smith, G.F.⁹

37
- 37049087486
- Y. Xu, and J. Zhang J. Chem. Soc., Chem. Commun. 1986 1606
- (1986) J. Chem. Soc., Chem. Commun. , pp. 1606
- Xu, Y.¹ Zhang, J.²

38
- 37049049704
- M. Green, and R.F. Hudson J. Chem. Soc. 1958 3129
- (1958) J. Chem. Soc. , pp. 3129
- Green, M.¹ Hudson, R.F.²

39
- 84961974409
- M.D. Liptak, K.C. Gross, P.G. Seybold, S. Feldgus, and G.C. Shields J. Am. Chem. Soc. 124 2002 6421
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 6421
- Liptak, M.D.¹ Gross, K.C.² Seybold, P.G.³ Feldgus, S.⁴ Shields, G.C.⁵

40
- 84961985847
- V. Barone, and M. Cossi J. Phys. Chem. A 102 1998 1995
- (1998) J. Phys. Chem. a , vol.102 , pp. 1995
- Barone, V.¹ Cossi, M.²

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