Indoline derivatives I: Synthesis and Factor Xa (FXa) inhibitory activities

Chemical and Pharmaceutical Bulletin

Volumn 54, Issue 2, 2006, Pages 163-174

  Noguchi, Tetsuji ^a   Tanaka, Naoki ^a   Nishimata, Toyoki ^a   Goto, Riki ^a   Hayakawa, Miho ^a   Sugidachi, Atsuhiro ^a   Ogawa, Taketoshi ^a   Asai, Fumitoshi ^a   Matsui, Yumi ^a   Fujimoto, Koichi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

Anticoagulant; Facter Xa (FXa) inhibitory activity; Indoline derivative

Indexed keywords

2 [4 [(1 ACETIMIDOYL 3 PYRROLIDINYL)OXY]PHENYL] 3 (7 AMIDINO 2 NAPHTHYL)PROPIONIC ACID; BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 10A INHIBITOR; INDOLE DERIVATIVE;

ANTICOAGULATION; ARTICLE; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULE; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 32044457418     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.54.163     Document Type: Article

References (24)

1. Davie E. W., Fujisawa K., Kisiel W., Biochemistry, 30, 10363-10370 (1991).
2. Al-Obeidi F., Ostrem J., Drug Discovery Today, 3, 223-231 (1998).
3. Elodi S., Varadi K., Thromb. Res., 15, 617-629 (1979).
4. Kaiser B., Hauptmann J., Cardiovasc. Drug Rev., 12, 225-236 (1994).
5. Weitz J. I., New Engl. J. Med., 337, 688-698 (1997).
6. Samama M.-M., Gerotziafas G. T., Thromb. Res., 109, 1-11 (2003).
7. Weitz J. I., Hudoba M., Massel D., Maraganore J., Hirsh J., J. Clin. Invest., 86, 385-391 (1990).
8. Hérault P., Bernat A., Pflieger A. M., Lormeau J. C., Herbert J. M., J. Pharmacol. Exp. Ther., 283, 16-22 (1997).
9. Fevig J. M., Wexler R. R., Ann. Rep. Med. Chem., 34, 81-100 (1999).
10. Nagahara T., Yokoyama Y., Inamura K., Katakura S., Komoriya S., Yamaguchi H., Hara T., Iwamoto M., J. Med. Chem., 37, 1200-1207 (1994).
11. Hara T., Yokoyama A., Ishihara H., Yokoyama Y., Nagahara T., Iwamoto M., Thromb. Haemost., 71, 314-319 (1994).
12. Hirayama F., Koshio H., Katayama N., Kurihara H., Taniuchi Y., Sato K., Hisamichi N., Sakai-Moritani Y., Kawasaki T., Matsumoto Y., Yanagisawa I., Bioorg. Med. Chem., 10, 1509-1523 (2002).
13. Brandstetter H., Kuhne A., Bode W., Huber R., von der Saal W., Wirthensohn K., Engh R. A., J. Biol. Chem., 271, 29988-29992 (1996).
14. Bartori G., Bosco M., Dalpozzo R., Todesco E. P., J. Org. Chem., 51, 3694-3696 (1986).
15. Huang W., Zhang P., Zuckett J. F., Wang L., Woolfrey J., Song Y., Jia Z. J., Clizbe L. A., Su T., Tran K., Huang B., Wong P., Sinha U., Park G., Reed A., Malinowski J., Hollenbach S. J., Scarborough R. M., Zhu B., Bioorg. Med. Chem. Lett., 13, 561-566 (2003).
16. Tsunoda T., Yamamiya Y., Ito S., Tetrahedron Lett., 34, 1639-1642 (1993).
17. Walsh D. A., Moran H. W., Shamblee D. A., Uwaydah I. M., Welstead W. J., Jr., Sancilio L. F., Dannenburg W. N., J. Med. Chem., 27, 1379-1388 (1984).
18. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M. C., Polidori G., Camalli M., J. Appl. Cryst., 27, 435 (1994).
19. Adler M., Davey D. D., Phillips G. B., Kim S.-H., Jancarik J., Rumennik G., Light D. R., Whitlow M., Biochemistry, 39, 12534-12542 (2000).
20. Otwinowski Z., Minor W., Methods Enzymol., 276, 307-326 (1997).
21. Jones T. A., Zou J. Y., Cowan S. W., Kjeldgaard M., Acta Crystallogr. Sect. A, 47, 110-119 (1991).
22. Brunger A. T., Adams P. D., Clore G. M., DeLano W. L., Gros P., Grosse-Kunstleve R. W., Jiang J. S., Kuszewski J., Nilges M., Pannu N. S., Read R. J., Rice L. M., Simonson T., Warren G. L., Acta Crystallogr. Sect. D Biol. Crystallogr., 54, 905-921 (1998).
23. Laskowski R. A., MacArthur M. W., Moss D. S., Thornton J. M., J. Appl. Crystallogr., 26, 283-291 (1993).
24. Y. Matsui is a member of the Structural Biology Sakabe Project (SBSP) of the Foundation for Advanced of International Science (FAIS).