Design, synthesis, and evaluation of fibrinogen inhibitors, ω-(p- amidinophenoxy)alkanoylaspartic acid derivatives

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 13, 1996, Pages 1443-1448

  Tanaka, Akito ^a   Sakai, Hiroyoshi ^a   Ishikawa, Takatoshi ^a   Nakanishi, Isao ^a   Ohkubo, Mitsuru ^a   Aoki, Toshiaki ^a   Motoyama, Yukio ^a   Takasugi, Hisashi ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 (4 AMIDINOPHENOXY)BUTYRYLASPARTYLVALINE; ANTITHROMBOCYTIC AGENT; ASPARTIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER SIMULATION; DRUG ACTIVITY; DRUG CONFORMATION; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; THROMBOCYTE AGGREGATION INHIBITION;

EID: 0030576303     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00246-6     Document Type: Article

References (31)

1. 1. Davies, M. J.; Thomas, A. C. Br. Heart J., 53, 363 (1985).
2. 2. Hamm, C. W.; Bleifield, W.; Kupper, W.; Lorenz, R. L.; Weber, P. C.; Wober, W. J. Am. Coll. Cardiol., 10, 998 (1987).
3. 3. Plow, E. F.; Pierschbacher, M. D.; Rouslahti, E.; Marguerie, G. A.; Ginsberg, M. H.Proc. Natl. Acad. Sci. USA., 82, 8057 (1985).
4. 4. Ruoslahti, E.; Pierschbacher, M. D. Science, 238, 491 (1987).
5. 5. Kieffer, N.; Phillips, D. F. Annu. Rev. Cell Biol., 6, 329 (1990).
6. 6. Gold, H. K.; Gimple, L.; Yasuda, T.; Ieinbach, R. S.; Jordan, R.; Iuliucci, J.; Coller, B. S. Circulation, 80 (Suppl. II), 267 (1989).
7. 7. a) Topol, E. J.; Califf, R. M.; Weisman, H. F.; Elis, S. G.; Tcheng, J. E.; Worley, S.; Ivanhoe, R.; George, B. S.; Fintel, D.; Weston, M.; Sigmon, K.; Anderson, K. M.; Lee, K. L.; Willerson, J. T.The LANCET, 343, 881 (1994).
8. b) The EPIC Investigators. N. Engl. J. Med., 330, 956 (1994).
9. 8. Coller, B. S. N. Engl. J. Med., 322, 33 (1990).
10. 9. Alig, L.; Edenhofer, A.; Hadvary, P.; Hurzeler, M.; Knopp, D.; Muller, M.; Steiner, B.; Trzecal, A.; Weller ,T. J. Med. Chem., 35, 4393 (1992).
11. 10. Cook, N. S.; Kottirsch, G.; Zerwes, H.-G. Drug of the Future, 19, 135 (1994).
12. 11. Zablocki, J. A.; Miyzno, M.; Garland, R. B.; Pireh, D.; Schretzman, L.; Rao, S. N.; Lindmark, R. J.; Panzer-Knodle, S. G.; Nicholson, N. S.; Taite, B. B.; Sayers, A. K.; King, L. W.; Campion, J. G.; Feigen, L. P. J. Med. Chem., 36, 1811 (1993).
13. 12. Blackburn, B. K.; Gadek, T. R. Ann. Rept. Med. Chem., 28, 79-88 (1993).
14. 13. a) Bondinell, W. E.; Callahan, J. F.; Huffman, W. F.; Keenan, R. M.; Ku, T. W. -F; Newlander, K. A. International Patent Application WO 93/00095 (1993).
15. b) Kopple, K. D.; Baures, P. W; Bean, J. W; D'Ambrosio, C. A.; Hughes, J. L.; Peishoff, C. E.; Eggleston, D. S. J. Am. Chem. soc., 114, 9615 (1992).
16. c) Reed, J.; Hull, W. E.; Lieth, C.-W; Kubler, D.; Suhai, S.; Kinzel, V. Eur. J. Biochem., 178, 141 (1988).
17. d) Mickos, H.; Bahr, J.; Luning, B. Acta. Chem. Scand., 44, 161 (1990).
18. e) Yamada, T.; Song, H; Inaka, K.; Simada, Y; Kikuchi, M.; Matsushima, M. J. Biol. Chem., 270, 5687 (1995).
19. 14. The active conformation is not always the same as its solution or crystal structure. Thus, these experimental reports on the RGD conformation are not evidence for the hypothesis that the active conformation of the RGD sequence is a type II' β-turn.
20. ab is the geometric mean of the k constants associated between atom a and atom b, and L is the distance between the two atoms divided by the sum of their radii,
21. b) Clark, M.; Cramer III, R. D.; Opdenbosch, N. V J. Comput. Chem., 10, 982 (1989).
22. 16. Oyasu, H.; Nakanishi, I.; Tanaka, A.; Murano, K.; Matsuo, M. J. Computer-Aided Molecular Design, 9, 171 (1995).
23. 17. a) A β-turn is usually classified under four types, namely type I, I', II, and II'.
24. b) See ref. 17c about the number of amino acid such as i, (i+1) or (i+2)th.
25. c) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol., 203, 221 (1988).
26. d) Crawford, J. L.; Lipscomb, W. N.; Schellman, C. G. Proc. Nat. Acad. Sci. USA, 70, 538 (1973).
27. 18. Krezel, A. M.; Wagner, G.; Uimer, S.-J.; Lazarus, R. A. Science, 264, 1994 (1994).
28. 19. Samnen, J.; Ali, F.; Romoff, T.; Calvo, R.; Sorenson, E.; Vasko, J.; Storer, B.; Berry, D.; Bennett, D.; Strohsacker, M.; Powers, D.; Stadel, J.; Nichols, A. J. Med. Chem., 34, 3114 (1991).
29. 3CN in 0.1 % TFAaq.; Flow, 118 ml/min; Detection, 254 nm; Retention time,8.0 min. Compounds 6-13 and 15-17 were prepared in a manner similar to that of 14.
30. 21. Born, G. C. R.; Cross, M. J. J. Physiol., 168, 178 (1963).
31. 22. Aoki, T.; Cox, D.; Senzaki, K.; Seki, J.; Tanaka, A.; Takasugi, H.; Motoyama, Y.z Tromb. Res., 81, 439 (1996).